R. v. Waddling-Leeson, 2025 ONCJ 395

Non-Publication and Non-Broadcast Order

A non-publication and non-broadcast order in this proceeding has been issued under subsection 486.4(1) of the Criminal Code. This subsection and subsection 486.6(1) of the Criminal Code, which is concerned with the consequence of failure to comply with an order made under subsection 486.4(1), read as follows:

486.4 Order restricting publication — sexual offences.

(1) Subject to subsection (2), the presiding judge or justice may make an order directing that any information that could identify the complainant or a witness shall not be published in any document or broadcast or transmitted in any way, in proceedings in respect of

(a) any of the following offences:

(i) an offence under section 151, 152, 153, 153.1, 155, 159, 160, 162, 163.1, 170, 171, 172, 172.1, 173, 210, 211, 212, 213, 271, 272, 273, 279.01, 279.02, 279.03, 346 or 347,

(ii) an offence under section 144 (rape), 145 (attempt to commit rape), 149 (indecent assault on female), 156 (indecent assault on male) or 245 (common assault) or subsection 246(1) (assault with intent) of the Criminal Code, chapter C-34 of the Revised Statutes of Canada, 1970, as it read immediately before January 4, 1983, or

(iii) an offence under subsection 146(1) (sexual intercourse with a female under 14) or (2) (sexual intercourse with a female between 14 and 16) or section 151 (seduction of a female between 16 and 18), 153 (sexual intercourse with step-daughter), 155 (buggery or bestiality), 157 (gross indecency), 166 (parent or guardian procuring defilement) or 167 (householder permitting defilement) of the Criminal Code, chapter C-34 of the Revised Statutes of Canada, 1970, as it read immediately before January 1, 1988; or

(b) two or more offences being dealt with in the same proceeding, at least one of which is an offence referred to in any of subparagraphs (a)(i) to (iii).

(2) MANDATORY ORDER ON APPLICATION. In proceedings in respect of the offences referred to in paragraph (1)(a) or (b), the presiding judge or justice shall

(a) at the first reasonable opportunity, inform any witness under the age of eighteen years and the complainant of the right to make an application for the order; and

(b) on application made by the complainant, the prosecutor or any such witness, make the order.

486.6 OFFENCE - (1) Every person who fails to comply with an order made under subsection 486.4(1), (2) or (3) or 486.5(1) or (2) is guilty of an offence punishable on summary conviction.

Ontario Court of Justice

DATE: 2025-07-24
COURT FILE No.: Toronto #22-70005649

BETWEEN:
His Majesty the King
— AND —
Charles Waddling-Leeson

Dangerous Offender Application
Before Justice Brock Jones
Heard on March 3-7, April 2, July 2 and 9, 2025
Reasons for Judgment released on July 24, 2025

Counsel:
P. Garcia — counsel for the Crown
A. Goldkind — amicus
C. Waddling-Leeson — self-represented

I. Introduction

[1] After a trial, on August 22, 2023, I found Charles Waddling-Leeson guilty of six charges:

• sexual assault while threatening to use a weapon: namely, a knife (Criminal Code section 272(1)(a));
• sexual assault causing bodily harm (Criminal Code section 272(1)(c));
• sexual assault while choking (Criminal Code section 272(1)(c.1));
• robbery (Criminal Code section 343(b));
• possession of property obtained by crime under $5000 (Criminal Code section 354(1)); and
• failing to comply with a probation order (Criminal Code section 733.1(1)).

[2] Following the convictions, the Crown applied to have Mr. Waddling-Leeson assessed to determine whether he met the criteria for a dangerous offender designation under section 752.1 of the Criminal Code. I granted the application on November 22, 2023.

[3] This is my decision regarding the Crown’s application to have the court designate Mr. Waddling-Leeson as a dangerous offender and to impose an indeterminate sentence of incarceration.

II. The Index Offences

[4] I reviewed the evidence and my findings of fact in detail in my trial judgment: see R. v. Waddling-Leeson, 2023 ONCJ 350. The following is a summary of those findings.

[5] Ms. A.A. was 24 years old on March 24, 2022. She was employed as a teaching assistant at what was then known as Ryerson University. During a scheduled class break, at approximately 5 p.m., she entered a women’s washroom.

[6] Mr. Waddling-Leeson entered the washroom after her. No one else was present. He confronted Ms. A.A. He pulled her iPhone from her pocket, throwing it across the room. He placed his hands on her, using one hand to restrain her arms. He pushed her, causing her to fall to the ground.

[7] She began to scream. He put one hand over her mouth to muffle her voice. He forced his penis into her mouth and said, “Suck on it, suck on it sexy.” She could not remember exactly how long this lasted. He then unbuttoned her pants and pulled them down along with her underwear. He performed oral sex on her.

[8] Ms. A.A. was unable to move. She was scared that he might hurt her further if she resisted.

[9] Mr. Waddling-Leeson next digitally penetrated her vagina and anus with his fingers. He warned her that he had a knife and if she made another sound, he would stab her. He touched her elsewhere on her body, including on her left breast. When she wouldn’t follow his instructions to open her mouth, he pressed his hands into her neck, and she felt his fingers gripping her skin. He pressed down so hard she felt like she couldn’t breathe and wondered if she would pass out.

[10] The assault ended when another woman entered the washroom and witnessed what was happening. She quickly left to call for help. Mr. Waddling-Leeson instructed Ms. A.A. not to move before exiting the washroom.

[11] Ms. A.A. was able to get help by contacting the authorities.

III. Victim Impact Statement

[12] The offences changed Ms. A.A.’s life. A simple trip to the washroom became a “catastrophic experience,” which has affected her physically, emotionally, and psychologically. She described her world as being “shattered.”

[13] She suffered from a concussion, had to take HIV prevention medication, has experienced severe insomnia, and has musculoskeletal injuries to her head, neck, and back. Her daily life has become “hard to bear.” A psychologist diagnosed her with post-traumatic stress disorder, panic disorder, heightened anxiety, and depression.

[14] She experienced severe side effects from the HIV prevention medication and had to put her education on hold. For two months, she hardly slept, and even years later, she continues to struggle with sleeping normally. She has lost control over her body and is in constant pain, requiring regular treatment from a physiotherapist.

[15] It is challenging for Ms. A.A. even to accept casual touching from others, such as hugs or handshakes. She is a “much more fearful person” than she could have imagined before the attack.

[16] While she was able to complete her teaching degree and is now employed as a teacher, she does not feel comfortable in her workplace. Tragically, she also no longer views schools as safe places for learning, given her terrible experience.

IV. Procedural History

[17] On the first day of the sentencing hearing, March 3, 2025, Mr. Goldkind informed me that his relationship with his client had deteriorated, and he no longer felt comfortable representing him as defence counsel. However, he was willing to remain as amicus and had no concerns about his ability to continue advocating on Mr. Waddling-Leeson’s behalf ethically, should I permit him to take on a particularly adversarial role for the sentencing hearing.

[18] Mr. Waddling-Leeson consented to this procedure. I informed him of his right to obtain new counsel. I connected him with a representative from Legal Aid Ontario to discuss his options, including a potential Rowbotham application and any concerns that might arise regarding Mr. Goldkind's role as amicus. After some time to reflect, he informed me that he did not wish to adjourn the proceedings to obtain a new lawyer. He was content to represent himself with the assistance of amicus.

[19] After the first five days of the sentencing hearing concluded on March 7, 2025, I adjourned the matter for further evidence and submissions. The case recommenced on March 21, 2025. Mr. Waddling-Leeson maintained that he wished to proceed without a new lawyer and with Mr. Goldkind acting as amicus.

[20] In R. v. Kahsai, 2023 SCC 20, at para. 33, the Supreme Court of Canada held that a trial judge has a “broad discretion to appoint amicus and determine the scope of their mandate”: see para. 50. The appointment of amicus can be appropriate where “complex issues or serious criminal charges made an adversarial perspective necessary for trial balance and fairness”: see para. 60.

[21] A dangerous offender hearing is a legally complex process, and the stakes for the accused person could not be higher. At the same time, an accused person has the fundamental right to represent themselves: see R. v. Swain, 1991 SCC 104, [1991] 1 SCR 933, per Lamer C.J., at p. 972. Mr. Waddling-Leeson made an informed decision to proceed in this manner.

[22] Mr. Goldkind was instructed to adopt an entirely adversarial stance towards the Crown and to raise any legal questions that would assist the court or help advance Mr. Waddling-Leeson’s position for a different sentence than that sought by the Crown. He made it clear that he would not encounter any conflict of interest that would prevent him from continuing in this role.

V. Background Of The Offender

[23] Mr. Waddling-Leeson has had a troubled life.

[24] He is currently 30 years old. He was born in Ajax, Ontario. His mother, Crystal Swatridge, raised him and his siblings, and he had a good relationship with her. He never knew his biological father, Roger, but described his stepfather, Roy, as supportive, although he felt that Roy preferred his biological children within the family.

[25] Mr. Waddling-Leeson self-reported that he did not witness or experience physical violence as a child. However, the Children’s Aid Society became involved with his family when he was only three years old due to allegations that his father was physically abusing him. There were also reports of neglect during the time he was in the care of his mother and stepfather. Ms. Swatridge reached out for assistance because she felt she could not cope with raising him alone, especially given his frequent tantrums.

[26] As a young child, Mr. Waddling-Leeson was prescribed medication for depression and to manage his mood. He often experienced multiple tantrums each day. Ms. Swatridge grew concerned that he might have been sexually abused by an adult male when he was only 9. However, Mr. Waddling-Leeson denied ever being sexually abused.

[27] The CAS remained involved following an allegation that he was sexually assaulting other children. The victims reported inappropriate touching and claimed he threatened them if they told anyone. They were frightened of him. Ms. Swatridge described him as “uncontrollable” at this time. Mr. Waddling-Leeson was referred to the Shoniker Clinic for care and treatment.

[28] He was also prone to fits of rage and violence. He put his fist through a wall and physically fought with his brother. His mother and stepfather reported to the CAS that he was physically aggressive, stating that he “hated women.” Ms. Swatridge described him attempting to burn down the house when he was 9 or 10 and using scissors against his brother.

[29] When he was 12, his mother had “lost all control of him.” When he was 13 or 14, he sexually abused a younger family member. The family eventually made the difficult decision to have him removed from the home.

[30] As a young person, Mr. Waddling-Leeson began interacting with the criminal justice system. He was arrested for assaulting his mother in 2010 and was subsequently charged with contacting her in violation of his release order. He accepted a voluntary placement with a local CAS.

[31] Later that year, the CAS had difficulty placing him in a group home due to his challenging behavioural issues. While at one group home, he engaged in sexualized conduct and was generally disobedient. As a result, he was soon placed on a youth probation order as well. He expressed dissatisfaction with having to follow the rules imposed by both the CAS and youth probation.

[32] He achieved brief success while residing at Youth Connections, a residential group home for youth with special needs, starting in February 2011. He attended school, followed the house rules, and appeared amenable to his living arrangements. Unfortunately, this did not last. By the end of 2011, he was implicated in selling and using drugs, as well as skipping school. On April 19, 2012, he was arrested for drug-related offences due to materials found in his closet. He was evicted from Youth Connections, and the same year, he was made a Crown ward.[1] He received counselling for anger issues and sexual misbehaviour.

[33] Eventually, Mr. Waddling-Leeson returned to live with his family for a brief period while still a teenager. Ms. Swatridge reported that he frequently stole and was consistently using drugs. His attendance at high school was poor.

VI. Criminal History

[34] Mr. Waddling-Leeson turned 18 on December 8, 2012. As an adult, he amassed a concerning number of criminal convictions for various offences. He has spent the majority of his adult life under a bail order, a probation order, or in custody. His criminal record was submitted as an exhibit in this hearing. For this judgment, I wish to emphasize some entries on that record that involve violence against women.

[35] As a young person, he was found guilty on November 18, 2010, of assaulting his mother. He forced his way into her residence and shoved her chest with two hands. He then struck her a second time with such force that she required immediate medical attention. After he was arrested and released, he was placed on an undertaking. One of the conditions of that undertaking prohibited him from attending at his mother’s home. He did so anyway and was arrested for failing to comply with that order. He was sentenced to 18 months’ probation.

[36] On March 1, 2017, following a trial, he was convicted of sexual assault, forcible confinement, and failing to comply with a probation order. He was at a house party and touched the 17-year-old victim’s vagina in a small bathroom without her consent. During the assault, he pushed her against a bathroom wall and put his hands over her mouth. He then pulled her pants and underwear down. She cried for him to stop. He was 21 years of age. Javed J. sentenced him to nine months in jail and two years' probation.

[37] After he was sentenced, Mr. Waddling-Leeson uttered a threat that he would “beat the living shit out of [the victim.]” This was about the victim who had just testified against him in the trial. He was convicted of that offence and sentenced to 45 days' jail.

[38] On June 21, 2015, Mr. Waddling-Leeson was convicted of threatening a woman and her son following a dispute he had with them at an apartment complex where he had been residing. He believed they had wronged him. He threatened to “come upstairs and kill” them. He was sentenced to the equivalent of 30 days in jail and 18 months' probation.

[39] On September 18, 2020, Mr. Waddling-Leeson pleaded guilty to one count of sexual assault. He had been residing at the victim’s house while visiting. While she was cleaning her washroom, he came at her from behind, and rubbed her rear end and breasts on top of her clothing. She told him to stop. Later, he groped her again and attempted to pull down her shorts. He was sentenced to 54 days served and placed on probation for two years.

[40] Following his convictions for the index offences by this court, Mr. Waddling-Leeson pleaded guilty to several other outstanding charges before North J., including breaking and entering into a hotel in Toronto and assaulting a woman who worked there. On March 24, 2022, he unlawfully gained access to 100 King Street West in Toronto. On the 65th floor, he encountered the victim, who was cleaning the area. She was vulnerable and alone. He pulled out a pair of scissors and pointed them at her, demanding keys to the offices. Fearing for her life, she fled. For these offences, and others, he received a global sentence of 21 months in jail.

[41] In total, Mr. Waddling-Leeson has been convicted or found guilty of more than 40 violent crimes (including the index offences) and 15 offences for failing to comply with court orders. This is in addition to drug-related offences and property crimes, such as breaking and entering and theft.

[42] His reporting habits while on probation have been poor. He was deemed non-compliant with probation and community supervision. He did not complete the requirement to participate in counselling (including for substance abuse, mental health, pro-criminal behaviours, or sexual offending) due to his non-attendance.

[43] His conduct while in custody has been troubling. He has been charged with institutional misconduct over two hundred times. Some of these incidents resulted in criminal charges being filed. For example, he was found guilty of over twenty criminal counts on December 10, 2024. He admitted to various acts of misconduct, including insulting staff, destroying jail property, and assaulting correctional officers, sometimes with his feces or urine.

[44] On July 9, 2025, he pleaded guilty to one count of assault and one count of mischief before me. Both charges related to criminal activity while he was held in custody at the Toronto South Detention Centre (“TSDC”). The facts of the offences were that on June 6, 2025, he intentionally damaged the fire sprinkler system in his cell. This triggered the fire alarm and prompted correctional officers to respond to a potential emergency. Water poured out of the sprinkler. The total damage was approximately $1000.

[45] On June 8, 2025, he threw a cup of his urine at the face of a nurse who was delivering medication to him. The liquid splashed down the right side of the victim, including her face, neck and shoulder. He said"That's for always checking if I take my medication." The assault interrupted the scheduled delivery of medication to other inmates on his unit.

[46] I sentenced him to two years and three months in custody for these offences, consecutive to any other sentence he was already serving.

VII. Dr. Klassen’s Testimony / Section 752.1 Report

[47] Dr. Klassen was qualified as an expert witness in forensic psychiatry. He examined Mr. Waddling-Leeson to prepare a Criminal Code section 752.1 assessment and testified over several days.

[48] While he generally found Mr. Waddling-Leeson to be pleasant and forthcoming, he was not fully cooperative. Dr. Klassen asked Mr. Waddling-Leeson to participate in phallometric testing, but he declined.

[49] Mr. Waddling-Leeson had little to no insight into his criminal tendencies. He stated that he is not a “sexual predator” and has no “unusual sexual desires.” He denied being impulsive. He claimed he was not aggressive as a child or teenager. He only took responsibility for his actions “sometimes.” When asked if he had any regrets about his prior actions, he stated, “Not really.” He described himself as “not a real violent man.”

[50] He has never held a “regular job” apart from some seasonal work for tradespeople. Instead, he has supported himself through Ontario Works and the sex trade. He described it as a source of “good money” and mused that he would like to be an actor in pornographic films upon his release from custody.

[51] He acknowledged a history of mental health concerns and some efforts at treatment. Dr. Klassen reviewed Mr. Waddling-Leeson’s prior medical records from various service providers. As a child, Mr. Waddling-Leeson was examined by Dr. Khattak at the Kids’ Clinic in 2010, who diagnosed him with ADHD, oppositional defiant disorder, conduct disorder, and cannabis misuse. As a young adult, Mr. Waddling-Leeson was examined by Dr. Zakaria from Lakeridge Health in 2014, when he was 19 years old. Dr. Zakaria reported that Mr. Waddling-Leeson experienced depression and anger and had a history of defiance, aggression, vandalism, and duplicity.

[52] While in custody as an adult, Mr. Waddling-Leeson repeatedly violated the institutional code of conduct. He regularly assaulted correctional officers. He was assessed by a psychiatrist in 2017, who concluded there was no evidence of psychosis or distress. Dr. Wesley arrived at the same conclusion in 2020. In 2021, while in custody, Mr. Waddling-Leeson was seen by Dr. Glancy from CAMH but declined psychiatric care. During the interview, he threatened to stab Dr. Glancy.

[53] Dr. Klassen interviewed Mr. Waddling-Leeson about his prior convictions. He took little to no responsibility for his crimes and offered no insight into the harm he caused his victims. For example, regarding the 2017 sexual assault, he denied there was any assault yet stated he just “took a plea.” That is false; he was convicted after a trial. He further described the victim as a “liar” to his probation officer. He had no memory of subsequently threatening the victim after the trial, despite his conviction for doing so. Regarding the 2020 conviction for sexual assault, he said he had a “playful” relationship with the victim and, after using cannabis, both thought they could “have a little fun.” She “blew it all out of proportion.”

[54] Regarding the index offences, he acknowledged that he did not know the victim beforehand, but told the police that he did. He blamed intoxication for his behaviour. He “couldn’t recall” if his offending behaviour was “impulsive.” He could not recall the assaults as he “blacked out" which directly contradicted his trial testimony that the sexual contact was purportedly consensual and he remembered the events. He also admitted he “made a story up.” He said he just “needed to use the washroom." When pushed by Dr. Klassen to explain why the offences would have occurred, he stated he could not tell him.

[55] Ms. Swatridge informed Dr. Klassen that her son has “never” expressed any guilt or remorse for his actions. In her assessment, he does not want “a normal life” and has “no intention” of changing his behaviour. He has not acknowledged any mental health difficulties and does not wish to receive any programming. Instead, he hopes to lead a life free from accountability.

[56] Dr. Klassen diagnosed Mr. Waddling-Leeson with antisocial personality disorder. Individuals with antisocial personality disorder fail to conform to social norms regarding lawful behaviour. They exhibit a pattern of disregarding and violating the rights of others. They may be deceitful and manipulative, making decisions without considering the consequences for themselves and others, for the sake of short-term personal gain. This diagnosis was partly based on his history of conduct-disordered behaviour exhibited since childhood. Troublingly, he has also demonstrated narcissistic personality traits, including a lack of empathy.

[57] Dr. Klassen assessed Mr. Waddling-Leeson using various actuarial methods for risk evaluation. He scored 29 out of 40 on the Psychopathy Checklist-Revised (PCL-R), which places him in the 80th percentile. This score indicates challenges with treatment responsiveness and community supervision. Mr. Waddling-Leeson's score on the Static-99R was 10, positioning him in the 99.99th percentile regarding re-offending. Additionally, he scored 37 on the Violence Risk Appraisal Guide-Revised (VRAG-R), corresponding to the 98th percentile for re-offending.

[58] Considering all available evidence, Dr. Klassen concluded that Mr. Waddling-Leeson was at a very high risk of future sexual and violent recidivism.

[59] Dr. Klassen emphasized that certain dynamic variables related to Mr. Waddling-Leeson’s offending behaviour could be targeted for treatment and supervision. These include his antisocial values and attitudes, his willingness to comply with community-based supervision, his lack of involvement in structured prosocial activities, and the establishment of realistic future goals. However, his willingness to change was, at best, uncertain, in Dr. Klassen’s opinion.

VIII. Efforts At Rehabilitative Programming

[60] While detained at the TSDC after his most recent arrest, Mr. Waddling-Leeson completed twelve one-hour programs. He did not complete any programs longer than an hour. Longer programs are available to offenders in pre-sentence custody, but he did not participate in any of them. Additionally, he did not complete any in-custody programs during his previous periods of pre-trial incarceration for prior criminal charges or sentences that were imposed prior to his commission of the index offences.

[61] Regarding community-based supervision, he told Dr. Klassen that he found probation “painful” in the past and struggled to work with his probation officers. In 2017, he informed his probation officer that he didn’t want counselling. He failed to report several times while under probation. His poor reporting habits hindered efforts to address any of the criminogenic factors that increased the likelihood of his re-offending. He never completed any counselling for substance abuse, mental health, or sexual offending. While on probation, he continued to re-offend. Ultimately, he was deemed unsuitable for future periods of community supervision.

[62] He was convicted nine times for failing to comply with a probation order. Mr. Waddling-Leeson also neglected to report after being placed on the national sex offender registry. He received two convictions for this offence.

[63] Nevertheless, he told Dr. Klassen that he would “do his best” to manage a long-term supervision order (“LTSO”) if one were imposed at the end of this hearing, rather than an indeterminate sentence of incarceration. On July 9, 2025, in court, during his right of allocution, Mr. Waddling-Leeson, however, expressed great frustration at the idea of being on a form of state-mandated supervision after he served any additional prison sentence I imposed, if that would result in him serving a sentence until he was 50 or older.

[64] He informed Dr. Klassen that he was open to sex offender treatment, including options that would involve medication and various psychotherapies. Dr. Klassen noted that “it is difficult to know whether these sentiments are sincere and genuine… and durable.” Mr. Waddling-Leeson has not demonstrated a history of following through or remaining committed to rehabilitative programming. He is prone to mood changes. In the past, he had made comments to his probation officer indicating that he did not like to take medication and preferred to “self-medicate” with marijuana.

[65] Of particular concern to Dr. Klassen was Mr. Waddling-Leeson's apparent lack of distress or concern regarding the course his life had taken. This included his numerous interactions with the criminal justice system and the time spent in custody. Consequently, his attitude could influence his commitment to making the necessary changes to prevent re-offending in the future.

[66] On August 3, 2023, Mr. Waddling-Leeson was sentenced to 11 months' jail by Moore J. On January 4, 2024, he was sentenced to 21 months, to be served consecutively to any other sentence he was currently serving, by North J. This resulted in Mr. Waddling-Leeson being transferred to a federal penitentiary. Records provided from the Correctional Service of Canada (“CSC”) when Mr. Waddling-Leeson was completing this recent aggregate federal sentence of over two years indicate that Mr. Waddling-Leeson has been assessed as requiring a high level of intervention based on a variety of factors.[2] However, Mr. Waddling-Leeson is noted to have expressed an interest in engaging with the required integrated correctional program model for sexual offenders and an associated high-intensity program for those offenders. Mr. Waddling-Leeson’s behaviour was also noted to have improved while in federal custody.[3] I will comment on this in greater detail later in this judgment.

IX. Institutional Misconduct and Demeanour In Court

[67] Mr. Waddling-Leeson has accumulated an astonishing number of infractions while in custody. These include formal criminal convictions as well as institutional findings that were documented but did not result in criminal charges. His institutional behaviour in provincial jails was described as “abysmal” by the Correctional Service of Canada.[4] However, it did acknowledge that he improved while serving a sentence in a maximum-security penitentiary from 2024 to the first half of 2025.

[68] The documented incidents of misconduct include destroying property, being disobedient, and assaulting staff and correctional officers. On one occasion, he also threatened a nurse who was administering medication to inmates. This behaviour predates his incarceration for the index offences and has occurred in multiple provincial jails. It began at least as early as 2015.

[69] Many of these assaults involve gratuitous and degrading behaviour intended to humiliate victims. Mr. Waddling-Leeson routinely threw feces, urine, and garbage at correctional staff. He would damage the sprinkler systems or sinks in his cells, causing flooding.

[70] When asked about these acts of misconduct, Mr. Waddling-Leeson did not express remorse. More than once, he expressed pride regarding this conduct.[5]

[71] On July 2, 2025, Mr. Waddling-Leeson appeared before me on Zoom. He was charged with new offences relating to his behaviour while in custody at the Toronto South Detention Centre. Those offences included an assault due to an incident on June 8, 2025. They had not been properly adjudicated, and he was presumed innocent of the allegations, although, as previously noted, he ultimately pleaded guilty to these offences on July 9, 2025.

[72] Mr. Waddling-Leeson immediately referred to the court in profane and demeaning language. He expressed a desire to plead guilty to these new offences. When the Assistant Crown Attorney put his position on the record for a six-month jail sentence, he became angry. He wanted to be sentenced to at least two years in prison. He used a highly derogatory term to describe the Assistant Crown Attorney and asked rhetorically if he wanted to give “breaks to criminals” and added that he “wished he could piss on [the Assistant Crown Attorney.]” He explained that he had recently served a sentence at a federal correctional institution but was transferred back to a provincial jail when he became eligible for statutory release. He told me he “threw piss” at a nurse and would keep “committing more charges” until he was transferred back to a penitentiary. He bragged that he had already assaulted more staff members. He showed no compassion for any of these victims.

X. Desire To Transition Into A Female Person

[73] During the sentencing hearing, Mr. Waddling-Leeson explained that he identifies as transgender and is in the process of transitioning to become a female person. He has requested the use of female pronouns while in custody. He has begun treatment to change his hormone levels, which includes using testosterone blockers and introducing increased levels of estrogen and progesterone. Additionally, he has started seeking funding for sex reassignment surgery.[6]

[74] Dr. Klassen was asked about the significance of Mr. Waddling-Leeson’s desire to transition from a risk-based perspective. Dr. Klassen testified that lowering Mr. Waddling-Leeson’s testosterone levels would diminish his sex drive. Dr. Klassen explained that he has worked at a gender clinic for many years, and the outcome of male-to-female transition usually involves surgical interventions, including castration.

[75] Dr. Klassen explained that the impact of feminizing hormones on aggression is not a well-studied topic. While there is generally a link between a person becoming more feminine and exhibiting less aggressive behaviour, each case is unique. The potential impact on Mr. Waddling-Leeson’s libido is also challenging to determine. The changes associated with chemical-based treatments could be reversed if Mr. Waddling-Leeson does not remain committed to taking them.

[76] For example, chemical castration, which involves administering certain drugs to reduce sexual arousal, is generally reversible, meaning that the effects typically cease or subside when the treatment is stopped. This contrasts with physical or surgical castration, which is a permanent procedure. If physical castration is performed, it is expected to affect his risk level of re-offending. However, no evidence was presented that Mr. Waddling-Leeson intended to undergo such a procedure.

[77] Throughout his interview with Mr. Waddling-Leeson, Dr. Klassen found him to be “vague and contemplative” about his desire to transition. Not everyone who begins the process of transitioning continues down that path. Given that Mr. Waddling-Leeson’s expressed intention to transition is relatively recent, Dr. Klassen would not change his opinion regarding Mr. Waddling-Leeson’s risk level at this time.

[78] Dr. Klassen was clear that while he felt qualified to answer these questions, there were limits to his expertise in this area. A physician specializing in treatments associated with transitioning would be better suited to provide expert opinion evidence in this regard.

[79] Correctional records further highlight Mr. Waddling-Leeson’s struggles with gender identity. After his arrest, he was housed mainly in male facilities during his detention for the index offences. However, he was transferred to Vanier, a women’s detention centre, on September 3, 2024. While held at Maplehurst Correctional Complex, he informed authorities that he identified as a woman and requested a transfer. He was then removed from Vanier on October 7, 2024, after breaching the behavioural contract required of all inmates there. During oral submissions on July 9, 2025, Ms. Garcia stated she was advised Mr. Waddling-Leeson was involved in a relationship with another inmate at Vanier. Federal correctional records indicate that Mr. Waddling-Leeson stated he met his “girlfriend” while staying at Vanier.[7]

[80] In 2024, Mr. Waddling-Leeson was placed in a penitentiary due to sentences imposed on him by other courts for different offences. He was assessed as requiring a high level of intervention. He downplayed his sexual assault convictions, describing them as only involving “touching and stuff”, and felt the way the criminal justice system had treated him was “ridiculous.”[8] He had a limited understanding of consent and personal boundaries. Nevertheless, he agreed to participate in the correctional plan developed for him, which included sexual behaviour programming. He explained that he considered himself a trans-female, and was prescribed medication for hormone therapy while in federal custody. His preferred name was Lolita, and he requested the use of female pronouns.

XI. Positions Of The Parties And Submissions Of Amicus

[81] On behalf of the Crown, Ms. Garcia submits that Mr. Waddling-Leeson should be designated a dangerous offender and sentenced to an indeterminate period of incarceration. He has a lengthy criminal record for crimes of violence, including sexual violence against women. The index offences were horrifying and will have a life-long impact on Ms. A.A.

[82] She asks me to find that despite spending nearly all his adult life in jail or subject to a form of state supervision, no sentence thus far has succeeded in controlling him or deterring him from re-offending. His risk of violent recidivism cannot be managed in the community or even governed while in custody. He has shown no meaningful commitment to treatment in the past and shows outright contempt for authority figures. He can experience outbursts of anger and lacks empathy for his victims. He is defiant and manipulative.

[83] His disorders should be deemed insurmountable. No treatment can overcome them. Where a determination that an offender’s risk may be safely controlled in the community is contingent on adequate community supervision as opposed to treatment, the resources necessary to implement the supervision must be available, capable of performance, and reasonable at the time of the dangerous offender hearing. The evidence at this hearing was that they are not resources capable of controlling Mr. Waddling-Leeson in the community. Therefore, nothing less than an indeterminate sentence is sufficient, and I cannot be satisfied that a lesser sentence will adequately protect the public.

[84] Mr. Waddling-Leeson agreed to being designated a dangerous offender. He requested a fixed sentence of 7 to 10 years.[9]

[85] Mr. Goldkind, as amicus, recommended a sentence of 8 – 12 years in custody followed by a 10-year LTSO. He submits that Mr. Waddling-Leeson was abused himself as a child. His ongoing unlawful behaviour is almost certainly a result of the trauma he likely experienced. While that does not excuse any of his criminal actions, it does help to explain what has gone wrong in his life. Unquestionably, he needs significant treatment and programming to reduce his risk of reoffending. And while the treatment he has been engaged with thus far has not succeeded, it has also not been sufficient to meet his needs.

[86] Mr. Waddling-Leeson’s conduct in custody, according to Mr. Goldkind, is unquestionably deplorable. However, provincial jails are not equipped to address his needs. When he was placed in a penitentiary, he did better. That explains his recent outbursts, in which he expressed his desire to return to that setting. At a federal prison, he will be able to complete the high-intensity programming necessary to address the underlying causes of his crimes of violence. The evidence further demonstrates that Mr. Waddling-Leeson does far better in a penitentiary on a day-to-day basis. His infractions for misconduct in provincial jails are not truly a reflection of Mr. Waddling-Leeson’s intractable violent behaviour, but rather a reflection of the reality of the conditions he experienced in those institutions.

[87] If Mr. Waddling-Leeson were sentenced to a lengthy prison term, he would have years to engage with the counselling and programming available to offenders of his nature. The environment where he would serve that sentence would be different from where he had been incarcerated for the vast majority of his prior time in provincial custody. There is a realistic possibility he might do far better there and demonstrate a capacity for change. He should be allowed to engage with this programming, which he has never been offered previously. Mr. Waddling-Leeson will also be subject to stringent supervision in the community by the CSC when placed on an LTSO following his time in a penitentiary. He will face the serious risk of additional punishment if he violates the terms of such an order. That deterrent effect will also serve as a check on any possible desire to reoffend.

[88] Mr. Goldkind further submits that Mr. Waddling-Leeson is now nearly 31 years of age. After serving a fixed sentence of up to 12 years, followed by a 10-year LTSO, Mr. Waddling-Leeson will be over 50 years old when he is finally released from correctional supervision. By that age, offenders are generally expected to have a dramatically reduced risk of re-offending. I should exercise extreme caution before assuming that at such a young age, Mr. Waddling-Leeson is beyond hope and that an indeterminate sentence is truly necessary.

XII. Dangerous Offender Sentencing Law

[89] A dangerous offender proceeding is a two-stage process. First, there is the designation phase; second, there is the penalty phase: see Boutilier at paras. 13-15. The designation phase “is concerned with assessing the future threat posed by an offender,” while the penalty phase “is concerned with imposing the appropriate sentence to manage the established threat”: see para. 31.

[90] In R. v. Currie, 1997 SCC 347, the Supreme Court held that the sentencing court must “be satisfied beyond a reasonable doubt of the likelihood of future danger than offender presents to society before he or she can impose the dangerous offender designation and an indeterminate sentence”: see para. 25. In Boutilier, the Supreme Court held that a finding of dangerousness requires the Crown to prove a “high likelihood of harmful recidivism and the intractability of the violent pattern of conduct”: see para. 46.

[91] In Boutilier, Côté J. noted that four criteria were established for a dangerous offender designation under the older (pre-2008) legislation, and that these criteria remain relevant under the current provisions: see para. 46. At paras. 26-27 Côté J. wrote:

In Lyons, Justice La Forest read the objective element of the designation — the requirement that the predicate offence be a “serious personal injury offence” — together with the subjective element — the “threat” assessment — and concluded that four criteria were “explicit” from the language of s. 753(1): (1) the offender has been convicted of, and has to be sentenced for, a “serious personal injury offence”; (2) this predicate offence is part of a broader pattern of violence; (3) there is a high likelihood of harmful recidivism; and (4) the violent conduct is intractable (p. 338). The last three criteria are part of the assessment of the “threat” posed by the offender. The last two of these are future-oriented, and Justice La Forest explained them as follows:

Thirdly, it must be established that the pattern of conduct is very likely to continue and to result in the kind of suffering against which the section seeks to protect, namely, conduct endangering the life, safety or physical well-being of others or, in the case of sexual offences, conduct causing injury, pain or other evil to other persons. Also explicit in one form or another in each subparagraph of s. [688, now 753] is the requirement that the court must be satisfied that the pattern of conduct is substantially or pathologically intractable. [Emphasis added; p. 338.]

[92] Justice Côté further commented on the requirement that the offender’s pattern of conduct is “substantially or pathologically intractable”: see Boutilier at paras. 26-27. Intractable conduct refers to “behaviour that the offender is unable to surmount.”

[93] Treatability of the offender must be considered at both stages. During the designation stage, treatability is crucial when the court assesses the threat posed by the offender. In the penalty phase, treatability aids in determining the appropriate sentence to manage the threat posed by the offender: Boutilier at para. 45.

[94] In R. v. Broadfoot, 2018 ONCJ 215, Justice Greene explained, at para. 77, how courts should analyze intractability at both the designation and sentencing stages:

At the designation stage, intractability relates to whether or not the conduct can be treated. At the sentencing stage, the court has found that the conduct cannot be treated so the question becomes can the conduct be managed. For example, in Boutilier, in looking at the issue of intractability at the designation stage, the court considered the depth of Mr. Boutilier’s addiction (as it was his addiction that made him dangerous). The trial judge concluded that the treatment prospects did not rise beyond an expression of hope. In looking at the issue of intractability at the sentencing stage, the court commented on Mr. Boutilier’s consistent failure to comply with conditions of his release which therefore led the court to conclude that supervision in the community would not adequately protect the public.

[95] At the penalty stage, the sentencing court must consider whether a lesser sentence than indeterminate detention would sufficiently protect the public: Boutilier at para. 63; Johnson at para. 44. In R. v. Straub, 2022 ONCA 47, the Ontario Court of Appeal held that the sentencing judge must “impose the least intrusive sentence required to reduce the public threat posed by the offender to the level statutorily required”: see para. 61. The judge must determine whether “the risk arising from the offender’s behaviour can be adequately managed outside of an indeterminate sentence”: see Boutilier at para. 31; R. v. Dadmand, 2022 BCCA 162, at para. 17.

Designation Phase: Is Mr. Waddling-Leeson A Dangerous Offender?

Analysis – Sections 753(1)(b)

[96] To achieve a dangerous offender designation under section 753(1)(b), the Crown must establish beyond a reasonable doubt:

i. That the offender has been convicted of a “serious personal injury offence”;

ii. That the offender, by his conduct in any sexual manner, including that involved in a predicate offence, has shown a failure to control his sexual impulses; and

iii. That such conduct has shown a likelihood of the offender causing injury, pain or other evil to other persons through failure in the future to control his sexual impulses.

See: R. v. Ahmed, 2023 ONCA 676, para. 20.

[97] In R. v. Sipos, 2014 SCC 47, the Supreme Court noted that the elements required for the designation are both retrospective and prospective in nature. Notably, the Crown must prove that the offender has failed in the past “to control his or her sexual impulses” and, that there is “a likelihood of causing injury, pain or other evil to other persons through failure in the future to control his or her sexual impulses”: see para. 20.

Serious Personal Injury Offence

[98] Sexual assault with a weapon and sexual assault causing bodily harm constitute serious personal injury offences for an application made under section 753(1)(b): see section 752(b).

Conduct In “Any Sexual Manner”

[99] The term “any sexual matter” has been interpreted broadly by the courts. In R. v. Currie, 1997 SCC 347, the Supreme Court determined that the term could refer to the predicate offence, although this was not essential. Provided the offender was involved in any sexual matter that demonstrated a likelihood of inflicting future harm, a dangerous offender application can succeed under (b). The Court noted that a trial judge is not required to focus on the objective severity of a predicate offence to conclude that a dangerous offender designation is warranted. At para. 22, the Supreme Court wrote:

First, the language of s. 753(b) explicitly states that there is no requirement to focus on the specific nature of the predicate offence. Section 753(b) provides that the prospective dangerousness of the offender is measured by reference to “his conduct in any sexual matter including that involved in the commission of the offence for which he has been convicted” (emphasis added). “[A]ny sexual matter” can refer to the predicate offence, but it need not. As long as the offender’s past conduct, whatever conduct that might be, demonstrates a present likelihood of inflicting future harm upon others, the designation is justified.

[100] Unlike sections 753(1)(a)(i) and (ii), the word “pattern” is not used in s. 753(1)(b). However, the Crown must prove a “pattern of offending in the past showing a failure to control sexual impulses”: see R. v. Lynch, 2022 ONCA 136, para. 50. The Crown may point to past harmful conduct of a particular kind, rooted in behaviour so intractable that it can safely be concluded that the same type of conduct is likely to manifest itself in the future”: see R. v. Patel, 2020 BCCA 92, para. 212.

[101] Two incidents may constitute a pattern, provided they demonstrate a sufficient degree of similarity: R. v. Hogg, 2011 ONCA 840, paras. 40, 43; R. v. Byers, 2017 ONCA 639, paras. 20-23. The pattern requirement is not based solely on the number of offences. It is also rooted in the elements of similarity in the offender's behaviour: R. v. Langevin, 1984 ONCA 1914, pp. 348-49. See also R. v. Knife, 2015 SKCA 82, para. 67, leave to appeal refused, [2015] S.C.C.A. No. 382.

Failure To Control Sexual Impulses

[102] A trial judge can conduct their analysis with the facts surrounding the offences, alongside a psychiatric expert opinion, to support a finding that the offender has failed to control their sexual impulses. In R. v. Sullivan, 1987 ONCA 6853, the Court of Appeal upheld a dangerous offender designation. It noted that it was acceptable for the trial judge to rely on “her [own] analysis on the facts underlying the two prior offences and the predicate offence,” in addition to psychiatric evidence, to demonstrate that the individual had and continues to demonstrate a failure to control his sexual impulses: see paras. 21, 30–34.

[103] The Court of Appeal in Lynch, supra, at para. 51, noted that:

In many of the reported cases of dangerous offender designations under s. 753(1)(b) or its equivalent, there was no dispute about whether the offender’s past conduct reflected a failure to control sexual impulses, and there was clear evidence of a pattern of such conduct.

[104] Importantly, an offender cannot initiate a sexual assault and then claim that evidence showing he terminated the assault before forcing intercourse on his victim demonstrates an ability to control his sexual impulses: see R. v. Sullivan, 1987 ONCA 6853.

[105] In R. v. Gibson, 2013 ONSC 589, (appeal dismissed: 2021 ONCA 530), Justice Code cited Sullivan and highlighted that the offender’s history of criminal behaviour and violence supported a “common sense inference” that there was an apparent failure to control the offender’s sexual impulses: see para. 15.

Likelihood Of Causing Pain, Injury or Other Evil

[106] In interpreting the term “likelihood” under section 753(1)(b), Justice Bell in R. v. C.G., 2019 ONSC 2406, concluded that “likelihood” connotes a degree of risk rising to at least a “probability” — that is, a risk that is more likely than not. The “likelihood” of future conduct occurring, as used in s. 753(1)(b), connotes a higher degree of certainty than the “substantial risk” requirement for a long-term offender designation in s. 753.1(1)(b). The Court, applying Boutilier, emphasized that the criterion is future-oriented and considers the offender's future treatment prospects.

Analysis – Section 753(1)(b)

[107] Mr. Waddling-Leeson has been convicted of sexual offences three times, in 2017, 2020, and 2023 (the index offences). These convictions establish a pattern of non-consensual behaviour with adult females. Additionally, he has exhibited aggressive and sexualized misconduct from a very young age. He has sexually assaulted family members, acquaintances, and strangers.

[108] He has also acted violently against women in a non-sexual manner. In 2015, he was convicted of uttering threats to a woman and her son over a minor dispute in his apartment building. In 2017, following his conviction for sexual assault before Javed J., he threatened the victim who had testified against him. In 2024, he was convicted by North J. of various crimes, including assaulting a female cleaning employee in a downtown office building with scissors. While in custody for the index offences in 2022, he threatened a nurse who was simply administering medication to other inmates.

[109] His potential victim pool is virtually limitless. He has chosen to sexually and/or violently assault family members, acquaintances, and even strangers without any provocation.

[110] Dr. Klassen’s expert opinion was that Mr. Waddling-Leeson is at a very high risk of future sexual (and violent) recidivism. I accept Dr. Klassen’s opinion evidence. He is an experienced psychiatrist with a long history of working with violent offenders. He interviewed Mr. Waddling-Leeson in person and reviewed a substantial amount of secondary source material. He has been declared an expert in forensic psychiatry by the Ontario Court of Justice and the Superior Court of Justice on countless occasions.

[111] Mr. Waddling-Leeson has not shown any meaningful insight into his offences or the harm he has inflicted on his victims. Since he was 16 years old, he has almost always been subject to a release order, probation supervision, or custody. Yet Mr. Waddling-Leeson has not been deterred by bail orders, probation orders, or incarceration. His behaviour has only deteriorated, with the index offences comprising the most serious entries on his extensive criminal record: see R. v. Cook, 2020 ONCA 809, para. 24.

[112] He is easily irritable and has threatened innocent members of the public with violence when frustrated or seeking to fulfill his own desires. He has engaged in little to no treatment, despite numerous court orders mandating it. While in custody, he has not completed any significant rehabilitative programming. He has previously refused treatment, including medication, and has not consented to undergo phallometric testing, which was suggested by Dr. Klassen. The significance of phallometric testing is that it can help determine whether Mr. Waddling-Leeson suffers from a paraphilic disorder that would require appropriate treatment in the future.

[113] Treatability must be considered when the court assesses the threat posed by the offender at the designation phase. I conclude that Mr. Waddling-Leeson does not accept the need for change, and his criminal history as a violent and sexual offender demonstrates that he is unable to control his impulses. Worryingly, as Dr. Klassen noted, he does not seem troubled by how his life choices have affected him and led to his ongoing interactions with the criminal justice and correctional systems. He believes there is nothing wrong with him.

[114] Dr. Klassen diagnosed Mr. Waddling-Leeson with anti-social personality disorder. Since his teenage years, he has shown a consistent pattern of disregard for and violation of his victims' personal autonomy. There is nothing in his past to indicate that he will adhere to treatment, whether in custody or not, and there is virtually no evidence that he will respond successfully to treatment even if he decides to cooperate. His attitude has been one of nearly constant defiance towards authority figures. He has also shown deceit to avoid accountability for his actions. By way of one very telling example, he admitted to Dr. Klassen that he “made up a story” about the index offences.

[115] This demonstrates, at the very least, avoidance, if not outright hostility to change, which must be considered at the designation phase: see R. v. S.M.J., 2023 ONCA 157, paras. 27-29. As Justice Code noted in Gibson, the existence of denial by sex offenders is a significant factor when assessing the likelihood test in section 753 regarding future re-offending. An unwillingness to undergo treatment is also relevant: see para. 45.

[116] In certain circumstances, Mr. Waddling-Leeson has demonstrated that he can control himself and collaborate with a medical professional. Dr. Klassen noted that he had no difficulty during his interview with Mr. Waddling-Leeson and suggested that it was possible for him to develop a positive relationship with future program or treatment providers.

[117] I further appreciate that Mr. Waddling-Leeson is still a relatively young man. Nevertheless, the evidence of his prior success with rehabilitative treatment is very thin, and I conclude that he is not meaningfully interested in his own rehabilitation. Mr. Waddling-Leeson has committed violent crimes repeatedly since he was a teenager. He resorts to violence when it suits him, despite the harm he causes to his victims.

[118] Mr. Waddling-Leeson has used force and threats to commit three sexual assaults against women. His anti-social personality disorder, lack of empathy, and refusal to engage with treatment or respect authority figures all contribute to the conclusion that he is likely to cause serious injury to others in the future due to his failure to restrain his sexual impulses: see, for example: R. v. Ahmed, 2023 ONCA 676, para. 123.

[119] I find that his offending behaviour is intractable. Mr. Waddling-Leeson is unable to overcome his impulses. He is neither treatable nor amenable to control. In R. v. J.C., 2025 ONCA 331, paras. 14-15, the Ontario Court of Appeal recently clarified how a sentencing court should assess intractability at the designation phase:[10]

Boutilier establishes that before designating a dangerous offender, a sentencing judge must be satisfied that the offender poses a high likelihood of harmful recidivism and that his or her conduct is “intractable”. The court defined intractable conduct as “behaviour that the offender is unable to surmount”: Boutilier, at para. 27. This requires the sentencing judge to conduct a prospective assessment of dangerousness, so that only offenders who pose a future risk are designated as dangerous and face the possibility of being sentenced to indeterminate detention.

The court in Boutilier further clarified that the prospective assessment of dangerousness necessarily involves the consideration of future treatment prospects: at para. 43. Offenders will not be designated as dangerous if their treatment prospects “are so compelling that the sentencing judge cannot conclude beyond a reasonable doubt that they present a high likelihood of harmful recidivism or that their violent pattern is intractable”: Boutilier, at para. 45.

[120] There are simply no compelling treatment prospects for Mr. Waddling-Leeson. I am satisfied beyond a reasonable doubt that Mr. Waddling-Leeson has a very high likelihood of reoffending sexually in the future. I am also satisfied that his offences will likely cause “injury, pain or other evil to other persons through failure in the future to control his sexual impulses.”

[121] To clarify, while he has participated in a very limited amount of rehabilitative programming to date, the evidence presented at the hearing does not establish a reasonable doubt concerning the issue of intractability or his high likelihood of reoffending: see R. v. Bird, 2023 SKCA 40, paras. 53-56.

Analysis – Sections 753(1)(a)(i) and (ii)

[122] Sections 753(1)(a)(i) and (ii) state that an offender may be designated a dangerous offender when the Crown proves the offender constitutes “a threat to the life, safety or physical or mental well-being of other persons based on evidence establishing

(i) a pattern of repetitive behaviour by the offender, of which the offence for which he or she has been convicted forms a part, showing a failure to restrain his or her behaviour and a likelihood of causing death or injury to other persons, or inflicting severe psychological damage on other persons, through failure in the future to restrain his or her behaviour, or

(ii) a pattern of persistent aggressive behaviour by the offender, of which the offence for which he or she has been convicted forms a part, showing a substantial degree of indifference on the part of the offender respecting the reasonably foreseeable consequences to other persons of his or her behaviour…”

[123] Ms. Garcia alternatively submits that Mr. Waddling-Leeson’s index offences, along with his criminal record for prior crimes of violence, constitute a “pattern of repetitive behaviour” and a “pattern of persistent aggressive behaviour” under these subsections.

[124] In R. v. Hogg, 2011 ONCA 840, the Ontario Court of Appeal held pursuant to subsection 753(1)(a)(i) that the pattern of repetitive behaviour, which includes the predicate offence, “has to contain enough of the same elements of unrestrained dangerous conduct to be able to predict that the offender will likely offend in the same way in the future”: see para. 40.

[125] The second element required for a designation under this subsection is the likelihood of the offender causing “death or injury to other persons, or inflicting severe psychological damage on other persons” through a failure to “restrain his behaviour” in the future. This is a very high standard that should, at a minimum, be equated with a probability, and may constitute something even greater: see R. v. Connell, 2022 ONSC 4703, para. 27.

[126] In R. v. Villeneuve, 2022 ONSC 2188, Justice Aitken held that the “persistence” required for the Crown to establish a pattern under subsection 753(1)(a)(ii) necessitates proof of behaviour that is “enduring, continuous, obstinately persevering, interminable or sustained”: see para. 103; see also R. v. Smith, 2023 ONCA 575, para. 56; R. v. Williams, 2018 ONSC 2030, para. 252.

[127] In R. v. Smith, 2023 ONCA 575, the Ontario Court of Appeal held at para. 37 that the court must be satisfied that:

(i) there is a pattern of behaviour
(ii) involving persistent acts of aggression causing serious harm and demonstrating a substantial degree of indifference to the consequences of the offender’s actions that
(iii) creates a serious risk of ongoing harm to the public.

[128] Regarding the requirement that the Crown prove a “substantial degree of indifference,” in Williams, Hill J. equated “indifference” with “disregard, lack of sympathy or empathy, callousness and coldness, and lack of concern or sensitivity.” That “indifference” must be examined through the lens of whether the offender has demonstrated any concern about how his actions “will impact others, are impacting others, or have impacted others”: see Villeneuve at para. 105.

The Crown Has Established The Pattern Under Both Subsections

[129] I am satisfied that the Crown has also proven the required pattern of behaviour under both sections 735(1)(a)(i) and (ii) beyond a reasonable doubt. In addition to my analysis in the previous subsection, I add the following.

[130] Mr. Waddling-Leeson has a continuous record of committing violent offences that dates back to his teenage years. Some of these offences resulted in serious harm to their victims, including assaults (against both civilians and officers), threats, and sexual assaults. He has assaulted individuals both in and out of custody. Nothing deters him.

[131] Regarding 735(1)(a)(i), the behaviour is repetitive and demonstrates a failure to restrain himself. It is highly likely Mr. Waddling-Leeson will offend violently in the future and therefore cause serious bodily harm to another victim, either physically or psychologically.

[132] Mr. Waddling-Leeson’s behaviour also satisfies the test in section 753(1)(a)(ii). His crimes of violence have been continuous and show a pattern of persistent aggressive behaviour. There is a substantial degree of indifference to his victims.

[133] He does not show remorse, nor does he acknowledge the serious harm his crimes of violence and sexual violence have caused to his victims. He offends whether in the community or in custody. He has been informed of the devastating harm done to his previous victims by prior courts. He has been told of the need to change his behaviour. Yet, he has not stopped offending, downplays or disregards the terrible harm he causes, and at times, has mocked his victims or questioned their character and honesty.

[134] For example, he referred to the 2017 sexual assault victim as a “liar” (Dr. Klassen’s report on page 27), referred to prior sexual partners as “sluts” (ibid), stated the victim of the 2020 sexual assault “blew it all out of proportion,” and generally takes pride in his conduct towards correctional officers while in custody (Dr. Klassen’s report on page 19; his statements in court before me on July 2 and 9, 2025).

XIII. Conclusion On Designation

[135] In summary, I am satisfied beyond a reasonable doubt that:

1. Mr. Waddling-Leeson has been convicted of a serious personal injury offence;
2. The index offences are part of a broader pattern of violent and sexually violent behaviour;
3. Considering his history of offending, including the index offences, he has furthermore shown a failure to control his sexual impulses as contemplated by Criminal Code section 753(1)(b);
4. There is a high likelihood that Mr. Waddling-Leeson will violently and/or sexually re-offend;
5. This reoffending will cause “injury, pain or other evil” through a failure to control his sexual impulses, and/or “injury” or “severe psychological damage” to other persons through failure in the future to restrain his behaviour;
6. Mr. Waddling-Leeson shows substantial indifference to the harm he causes his victims; and
7. Mr. Waddling-Leeson’s violent and sexual offending behaviour is intractable.

[136] I therefore find that Mr. Waddling-Leeson has shown a failure to control his sexual impulses, and there is a likelihood that he will cause injury, pain or other evil to other persons through failure in the future to control those sexual impulses. I designate him a dangerous offender pursuant to section 753(1)(b). I also find that Mr. Waddling-Leeson constitutes a threat to the life, safety or physical and mental well-being of other persons and designate him a dangerous offender pursuant to sections 753(1)(a)(i) and (ii).

XIV. Penalty Phase: What Is The Appropriate Sentence?

[137] There are three sentencing options for an individual designated as a dangerous offender. They may receive a standard sentence, a determinate sentence of incarceration of at least two years followed by an LTSO of up to 10 years, or a sentence of an indeterminate period of incarceration: see Criminal Code section 753(4).

[138] As previously noted, Criminal Code section 753(4.1) requires that the court sentence the offender to an indeterminate period of imprisonment “unless it is satisfied by the evidence adduced during the hearing of the application that there is a reasonable expectation that a lesser measure… will adequately protect the public against the commission by the offender of murder or a serious personal injury offence.” However, there is no presumption in law of an indeterminate sentence for someone designated as a dangerous offender.

[139] The requirement that indeterminate detention must be imposed where the judge is not satisfied there is a “reasonable expectation” that a lesser sentence will adequately protect the public against the commission of murder or a serious personal injury offence was upheld as a “rational means to achieve the public protection objective” inherent to the dangerous offender regime: see Boutilier at para. 76. The term “reasonable expectation” should be interpreted as a “likelihood”, “a belief that something would happen”, or “a confident belief for good and sufficient reasons”: see Straub at para. 30. It is a more stringent requirement than a “reasonable possibility”: see Straub, supra, citing R. v. Groves, 2020 ONCA 86, para. 15.

[140] When determining whether the dangerous offender’s behaviour is manageable, a court should consider:

1. Evidence that the offender avoided treatment;
2. Failed to respond to or terminated treatment;
3. Breached court orders;
4. Lacked motivation;
5. Continued to be involved in high-risk conduct;
6. Remains afflicted by a serious personality disorder; and
7. Demonstrates a high risk to engage in violent recidivism.

See Straub at para. 64; R. v. K.P., 2020 ONCA 534, para. 13.

[141] I may only consider an indeterminate sentence if I rule out the appropriateness of lesser sentencing options. If I am satisfied that a conventional sentence will adequately protect the public from the commission of a subsequent serious personal injury offence, then I must impose such a sentence. Second, if I find that a conventional sentence would not meet this standard, I must consider whether I am satisfied that a conventional sentence of a minimum of two years in jail, followed by an LTSO for a period of up to 10 years, will sufficiently protect the public from the same concern.

[142] Given the parties' positions, the primary issue for me to decide is whether a fixed sentence of at least seven years followed by a 10-year LTSO will adequately protect the public, or whether Mr. Waddling-Leeson must be sentenced to an indeterminate period of incarceration.

Likelihood Of Control In The Community

[143] An assessment of whether an offender’s risk can be safely managed in the community must consider the available community supervision options. In R. v. Bitternose, 2013 ABCA 220, the Alberta Court of Appeal stated that a sentencing court must determine “if there is evidence that facilities to provide the necessary degree and type of supervision are available, and that such supervision is reasonable”: see paras. 11-13; R. v. Napope, 2023 SKCA 1, para. 35.

[144] The evidence presented at this hearing indicated that a long-term supervision order cannot adequately replicate the equivalent of 24-hour supervision available in a prison, regardless of the offender's place of residence. The primary purpose of the dangerous offender provisions in the Criminal Code is to protect the public, and resource limitations must be taken into account in my decision. If an offender cannot be managed in the community except under essentially 24-hour, 7-day-a-week “jail like” conditions, they must receive an indeterminate sentence: see R. v. D.V.B., 2010 ONCA 291, paras. 59-60.

[145] In Dr. Klassen’s opinion, while Mr. Waddling-Leeson has shown some openness to treatment, it is difficult to determine if this is sincere and sustainable. His attitude fluctuates. He has never previously demonstrated an ability or willingness to engage with treatment in the medium or long term. My observations of Mr. Waddling-Leeson in court indicate that he is volatile and prone to unpredictability. Some days, he would refuse to come to court; other days, he would attend and actively listen. Occasionally, he would express anger and frustration, acting out and making it difficult or impossible for the court to continue with his case. On multiple occasions, he disparaged amicus or the court.

[146] As Dr. Klassen noted, there is a genuine fear that Mr. Waddling-Leeson might entirely abandon any willingness to comply with a community-based supervision plan, even with the threat of a breach charge hanging over him. Prior experience with the criminal justice system, including incarceration, has not deterred him from disobeying court orders, failing to report, or re-offending. If he were released into the community, even under an LTSO and placed in a residential facility supervised by the CSC, he might eventually leave or refuse to follow the conditions imposed on him. This is a very valid concern, as he has shown little attachment to anyone or any place in the past. If he were to evade state supervision, there is a high likelihood of his violently or sexually reoffending. Indeed, without prolonged and effective treatment, it is nearly certain.

[147] Mr. Waddling-Leeson’s repeated victimization of women remains highly concerning. Despite multiple convictions for sexual assault, he has shown no insight into mistreating women or improving his understanding of the importance of obtaining informed consent before engaging in sexual activity. He regards his treatment by the justice system for these offences as “ridiculous”. That he could hold such a view of his horrific abuse of Ms. A.A. in particular is frightening. Based on his criminal convictions alone, his lack of insight into his behaviour, and his inability to be deterred, I find he cannot be safely controlled in the community.

[148] In addition, even while in custody, his predatory behaviour has persisted. He was transferred to Vanier by the provincial correctional authorities despite his criminal record for sexual and physical violence against women. Setting aside the propriety of this decision, which was outside the jurisdiction of the court, I feel compelled to note that I was alarmed when counsel first brought this development to my attention. At Vanier, Mr. Waddling-Leeson was able to pursue an inappropriate relationship with a female inmate. As Ms. Garcia correctly noted during final submissions, this kind of behaviour within an institution is strictly forbidden, as inmates are often vulnerable. They may have mental health issues or have experienced trauma in their lives. Their rehabilitation process can be complex. Allowing another inmate to influence them emotionally in this manner could expose them to duress or other forms of intimidation. It can set a vulnerable inmate back and cause re-traumatization. Additionally, the risk of physical or sexual abuse is always present.

[149] I have limited evidence of what happened between Mr. Waddling-Leeson and this other inmate. I can only conclude that he broke the code of conduct expected of inmates at Vanier and referred to this other person as his “girlfriend” to federal correctional authorities, which suggests he viewed the relationship as romantic or intimate in nature. It is another example of how he will violate any rules placed upon him to satisfy his desires.

[150] Evidence of treatability must demonstrate that the offender can be treated within a defined timeframe. It must establish something more than mere “speculative hope”: see R. v. A.R., 2022 ONCA 553, para. 33; Straub at para. 63.

[151] Dr. Klassen testified that there is nothing in Mr. Waddling-Leeson’s history to suggest that Mr. Waddling-Leeson will respond positively to a community-based plan. While it is not impossible to imagine he might comply, in my assessment, it is entirely speculative to conclude he would do so beyond the very short term. He has not shown that he responds to treatment in custody or within the community; in fact, his track record indicates the opposite. He does not respond well to any form of supervision or authority figure and does not acknowledge that he is violent, dangerous, and needs to change.

[152] Mr. Waddling-Leeson requires a level of structure and supervision that can only be provided in a carceral setting. The Crown has proven beyond a reasonable doubt that there is no “reasonable expectation” that a lesser measure will adequately protect the public from the commission of another serious personal injury offence.

[153] It bears emphasizing that Mr. Waddling-Leeson’s conduct in court is another factor that demonstrates he is not yet committed to his rehabilitation. He was regularly defiant and disrespectful. Notably, on July 2, 2025, he was explicit that he would continue committing offences while in custody at a provincial jail to achieve his goal: a longer sentence and a transfer to a federal institution. This is yet another example of how he has no difficulty using violence to obtain what he wants and demonstrates little to no empathy for his victims. He openly told me that it was his intention to continue with his assaultive behaviour as he believed that would inevitably result in him receiving a sentence greater than two years. He also showed utter contempt for the integrity of the proceedings and the authority of the court. An offender’s conduct in court is a factor to consider when assessing his level of risk and whether he can be realistically and effectively controlled in the community: see Straub at para. 78; R. v. Erstikaitis, 2019 ONSC 6863, para. 44; R. v. Heaton, 2018 BCPC 136, para. 188.

[154] Mr. Goldkind noted that Mr. Waddling-Leeson has not yet been offered, nor has he been able to participate in, the high-intensity supervision or treatment provided by the CSC. I do not find this persuasive. In R. v. Bennett, 2013 ONCA 471, the Ontario Court of Appeal held that a sentencing court cannot find a reasonable expectation of control in the community based solely on the fact that the offender has not yet tried (and failed) to comply with certain programs. An “indication of potential” is not sufficient: see para. 8.

[155] A similar argument was presented in R. v. S.R., 2025 ONSC 929. The offender’s prior record primarily included short reformatory sentences and one penitentiary sentence from 20 years ago. Justice Barrett cautioned that sentencing courts must not erroneously treat a fixed sentence with an LTSO as “a test run for any expression of hope that might exist”: see para. 168. When the evidence does not demonstrate a reasonable expectation that the offender could be controlled in the community, an indeterminate sentence is required.

[156] Similarly, Mr. Waddling-Leeson’s intention to transition to a female identity does not alter my conclusion. I have no doubt this is a difficult process for him to endure and brings deep emotional challenges. He may face significant hardships in the future as a result of this decision, especially while in custody. Even if I could conclude that his desire to transition is genuine, I cannot speculate on what effect, if any, it would have on his future level of dangerousness. Ms. Garcia described the limits a sentencing court can impose on a new, untried treatment well in her written submissions:

The possibility of engaging in a new, yet untried treatment option does not render the offender manageable in the community. Neither is not having previously failed or refused treatments. These aspects are relevant, but in no way determinative of the final assessment, which is based on the evidence as a whole. Dangerous offenders often have a wide range of mental health and addiction challenges. There are a vast number of treatments, be that psychological, behavioural, pharmacological, or otherwise, that they may engage with throughout their lives. No individual will try all forms of treatment.[11]

[157] In R. v. Williams, 2025 ONCA 327, the appellant argued that the trial judge should have found he could have been adequately supervised in the community based on “the availability of new and improved medications and other treatment modalities that would more effectively treat him.” The Court of Appeal found no error in the trial judge’s conclusion that “mere hope that treatment will be successful or some optimism that an offender could be rehabilitated is not a sufficient basis to impose a determinate sentence”: see paras. 11-12. The trial judge’s decision to impose an indeterminate sentence was upheld.

[158] I recognize that I am not required to conclude that treatment can eliminate risk or cure underlying causes of criminal conduct. What is proposed needs only to realistically reduce the risk posed by the offender to a manageable level. The focus at this stage of the proceeding is on risk management, and a court should not require a plan that would offer complete elimination of risk: Straub at para. 48.

[159] Nevertheless, the extraordinary public safety concerns presented by Mr. Waddling-Leeson cannot be dismissed by placing blind faith in an untested form of treatment. Furthermore, after considering all the evidence presented at this hearing, I conclude that Mr. Waddling-Leeson is not motivated to meaningfully engage with any form of treatment or to accept and confront the causes of his offending behaviour: see A.R. at para. 28; R. v. Wielgosz, 2023 ONCA 550, para. 7.

Conclusion On Penalty

[160] I am satisfied that the Crown has proven beyond a reasonable doubt that there is not a reasonable expectation that a lesser measure than an order for indeterminate detention will adequately protect the public from a future serious personal injury offence.

[161] Mr. Waddling-Leeson will be sentenced to an indeterminate term of imprisonment.

XV. Ancillary Orders

[162] The following ancillary orders are also made. First, an order pursuant to Criminal Code section 760 to produce to Correctional Services Canada:

(i) Dr. Klassen’s report and a transcript of his testimony;
(ii) A copy of my reasons for conviction and sentencing;
(iii) A transcript of the entirety of the trial and sentencing proceedings; and
(iv) Any other sentencing materials filed on this hearing.

[163] Mr. Waddling-Leeson is prohibited from having any contact, directly or indirectly, with Ms. A.A., the victim of the index offences, pursuant to section 743.21.

[164] A DNA Order pursuant to s. 487.051 (the index offences are primary designated offences).

[165] An order that Mr. Waddling-Leeson comply with the Sex Offender Registration Act, S.C. 2004, c. 10, for life, pursuant to section 490.013(6).

[166] A weapons prohibition order for life pursuant to s. 109.

[167] The victim fine surcharges are waived.

Released: July 24, 2025
Signed: Justice Brock Jones

Footnotes

[1] The correct terminology now is a child in extended society care, due to the enactment of the Child, Youth and Family Services Act, S.O. 2017, c. 14. As the older term was used in the documents that were provided to me for this hearing, I have relied upon that language accordingly.

[2] On August 3, 2023, Mr. Waddling-Leeson was sentenced to 11 months. On January 4, 2024, he was sentenced to 21 months, to be served consecutively to any other sentence being served. On May 13, 2025, Mr. Waddling-Leeson was transferred back to a provincial jail, where he had been held pending the completion of these proceedings.

[3] Updated CSC Records, Exhibit 21, page 50.

[4] Letter from the Parole Board of Canada, dated May 2, 2025, located in Exhibit 21, at page 82.

[5] For example, he referred to one incident and justified his conduct by stating he “wanted to send the nerd CO home”: see Summary of Misconducts, Vol. 2., Tab 18 MHCC Records, p. 5.

[6] I have referred to the offender as Mr. Waddling-Leeson in this judgment and have used male pronouns as he was charged under that name.

[7] Updated CSC Records, Exhibit 21, page 72.

[8] Updated CSC Records, Exhibit 21, page 23.

[9] Despite Mr. Waddling-Leeson’s concession that he be designated a dangerous offender, I have held the Crown to its burden of proof.

[10] My emphasis added.

[11] Crown’s written submissions, page 85, para. 220.