CITATION: R. v. O’Brien, 2026 ONSC 2889

COURT FILE NO.: CR-22-70000633-0000

DATE: 20260520

BETWEEN:

HIS MAJESTY THE KING

– and –

ROBERT O’BRIEN

Patricia Garcia and Matthew Boissoneault, for the Crown

Dean Embry, Amicus Curiae

HEARD: March 2, 3, 4, 5, 16, 2026

I. OVERVIEW... 2

II. HISTORY OF THE CASE.. 2

III. BACKGROUND.. 3

(a) The Index Offence. 3

(b) Mr. O’Brien’s Circumstances. 3

(d) Mr. O’Brien’s History Of Mental Health Assessment And Treatment 6

(e) Dr. Gray’s Diagnosis. 11

(f) Dr. Gray’s Assessment of Risk. 12

IV. ISSUES. 13

V. ANALYSIS. 14

(a) Is Mr. O’Brien A Threat Based On A Pattern Of Repetitive Behaviour?. 14

(b) Is Mr. O’Brien A Threat Based On A Pattern Of Aggressive Behaviour?. 18

(d) Conclusion: A Dangerous Offender Designation Is Warranted. 23

VI. DISPOSITION.. 24

1This case is very tragic. Robert O’Brien has spent most of his adult life in prison. He is, regrettably, a person with low cognitive skills and significant mental illnesses. He has no one in the community who can really support and assist him. He appears to prefer jail to life on the outside.

2Mr. O’Brien has pleaded guilty to one count of robbery. It is one of many robberies (and other crimes) that he has committed. The Crown applies for the Court to declare that he is a dangerous offender and sentence him to an indeterminate period of incarceration. What follows are my reasons on this application.

II. HISTORY OF THE CASE

3Mr. O’Brien appeared before me on June 26, 2024, for an open court judicial pre-trial. He had retained Dean Embry. He then discharged Mr. Embry. A trial date in March 2025, had been set.

4From having dealt with Mr. O’Brien from time to time, and from the tenor of discussions with counsel, it was evident that he had mental health issues. Mr. Embry, a highly experienced defence lawyer, was willing to act as amicus curiae. He is known by the bench and the bar as an expert in mental health law. I am grateful that he was willing to act as amicus in a case involving a difficult and very troubled accused person.

5As Mr. O’Brien was formally unrepresented, an open court pre-trial was required. It proved very challenging. On June 26, 2024, he refused to leave his cell and attend court. On July 11, 2024, he was at the Centre for Addiction and Mental Health on a Form 1. He also refused to leave the secure forensic ward that day. On September 10, 2024, Mr. O’Brien appeared remotely and indicated that he did not have a new lawyer. On October 4, 2024, Mr. O’Brien refused to appear again. On December 3, 2024, however, he appeared remotely and tried to plead guilty. I refused to let him as he was unrepresented. The Crown was seeking an assessment order under s. 752.1 of the Criminal Code and, potentially, a dangerous offender designation. I explained to Mr. O’Brien that a guilty plea could have significant consequences. I advised him to speak to counsel.

6On December 5, 2024, Mr. O’Brien appeared remotely again. He indicated that he wished to plead guilty. Mr. Embry was present as amicus. I conducted a very lengthy plea inquiry with him. I was satisfied that he was fit (so was Mr. Embry) but concerned that he may not have fully understood the consequences of a guilty plea. As a result, I spent a great deal of time on the plea inquiry. Once I was satisfied that Mr. O’Brien’s plea was informed and voluntary, I agreed to accept it.

7Because of the very lengthy period Mr. O’Brien had been in custody at that point, I granted the Crown only a very short period to prepare an application for an assessment. The application was brought on December 17, 2025. It was apparent to me that Mr. O’Brien met the very low threshold for ordering an assessment. I signed the order on January 28, 2025, appointing Dr. Jonathan Gray, a forensic psychiatrist, as assessor.

8Mr. O’Brien has spent his entire life encountering and colliding with government institutions. These institutions include the Catholic Children’s Aid Society of Toronto (“CCAS”), the criminal justice system, the mental health system, and the prison and penitentiary system. As a result, many, many records were generated. It took a great deal of time to gather the records and provide them to Dr. Gray. Dr. Gray prepared his report without interviewing Mr. O’Brien or analysing psychological tests that Mr. O’Brien participated in. Mr. O’Brien refused to be interviewed by him or to cooperate with the assessment process in any way.

9Dr. Gray submitted his report on August 18, 2025. The dangerous offender hearing was held during the week of March 2, 2026. The Crown called three witnesses:

Adrian Alexander, a parole officer with Correctional Services of Canada (“CSC”);
Jennifer Quirk, a correctional officer with the Ministry of the Solicitor General; and,
Dr. Gray.

10Closing submissions were made on March 16, 2026.

11I found all three witnesses to be credible and helpful. As will become obvious, however, the evidence of Mr. Alexander and Ms. Quirk was less relevant to the key issues in this hearing. Dr. Gray’s evidence, on the other hand, was very important. I found that Dr. Gray’s evidence was very helpful on the key issues. His credibility and his findings were not significantly challenged.

III. BACKGROUND

(a) The Index Offence

12On November 27, 2021, Robert O’Brien went to a branch of the Toronto Dominion Bank in Toronto. Just before 3:00 pm he went up to a teller. He told her: “Give me $10,000.00. I have a bomb. I will kill you.” His left hand was concealed in his jacket pocket. The teller told him she did not have that much money. He told her to give him what she could. She went to the cash drawer and gave him $165.00. That cash included a GPS tracker. She also gave him a further $200 in cash. Mr. O’Brien left. The bank staff called the police and the GPS company. The police were able to track the cash to Homewood Avenue and Carlton Street. Two police officers arrested Mr. O’Brien. They searched him incidental to arrest. They found the cash in his sock. Mr. O’Brien has been in custody ever since.

(b) Mr. O’Brien’s Circumstances

13Everything about Mr. O’Brien’s background is tragic. There are, for example, 1,664 pages of Historical Child In Care records from the CCAS. Except for 9 years with the Lee family, his life has been marked by instability since the day he was born.

14Much of the information set out here is found in the Dr. Gray’s report. Dr. Gray had access to eight volumes of records, including records from the CCAS; records from Correctional Services of Canada; youth records; medical records; school records; records from the Ministry of the Solicitor General; and transcripts of various court appearances. Those materials were filed as part of the dangerous offender hearing.

15Mr. O’Brien was born on December 6, 1977. His mother, Donna O’Brien, was 16 years old when she gave birth to him. Donna O’Brien was receiving treatment for substance abuse at the Browndale Treatment Centre when she gave birth. Mr. O’Brien’s father was a resident at the same treatment centre. Mr. O’Brien was admitted to the care of the CCAS 10 days after he was born. Mr. O’Brien went to two different foster mothers before being placed back with his mother in 1980. She was about 19. She was simply unable to cope. She placed Mr. O’Brien up for adoption in 1981. She requested custody again when she finished a treatment program, but she struggled again with him. Ms. O’Brien gave him over to the care of the CCAS and in 1981 he was placed with Robert and Patricia Lee. He was formally made a Crown ward in May 1981 when he would have been about 3 ½ years old. Dr. Gray states in his report:

Mr. O’Brien was made a Crown ward on May 19, 1981, initially with no access to his biological family members, because of “severe emotional neglect and deprivation” and his teenage mother being unable to adequately care for him. His child protection worker from the CCAS, Mary Carpenter Smith, described him in her June 15, 1989 affidavit as “emotionally disturbed as of the finding of Crown wardship and remains so”.

16Mr. O’Brien was placed with the Lee family in February 1981 as a foster child. He would have been just over 3 years old. He stayed with the Lee family for nine years. During that time, he attended special schools for children with behavioural and academic difficulties. School records show that he was frequently aggressive and abusive towards staff and other students. He was, however, capable of completing assignments and doing his schoolwork although with frequent mistakes. He was easily frustrated. He was prescribed Ritalin for his ADHD and remained on that drug on and off from the age of six.

17In 1989 Mr. O’Brien began to have more contact with his mother. Dr. Gray suggests that this contact was a cause of the decline in Mr. O’Brien’s behaviour and the escalation of his difficulties. His mother was impulsive and had plenty of her own problems. Her other child had been removed from her care, and she was arrested and detained after setting fire to her apartment. Mr. O’Brien was angry with her for giving him up. The visits caused him enormous anxiety, and he eventually refused to see her. His anxiety escalated and he became a major worry for his foster parents. They found it difficult to deal with him. In February 1990 Ms. Lee asked that the CCAS remove Mr. O’Brien from the Lee home. Ms. Lee felt overwhelmed and unable to care for him. This was a shock for Mr. O’Brien, as, according to one case worker, he had “very much bonded to his foster parents and he is regarded by them and indeed feels himself to be a full member of the family.” Dr. Gray does not say so directly in his report, but it is apparent that he believes that this was a highly traumatic event for Mr. O’Brien.

18Mr. O’Brien was then placed in a series of group homes. Unfortunately, he established a pattern of petty criminality, failing to follow rules, and escalating violent behaviour. The director of his first group home – who had no medical qualifications – took him off Ritalin, a medication designed to deal with attention deficit hyper-activity disorder (“ADHD”). He was described as “defiant, out of control” by one group home. He was suspended from time to time from schools for aggressive behaviour. In 1991, at about age 14, he was charged with assaulting the principal and vice-principal of his school. He continued to accumulate charges. He continued to be transferred from group home to group home when he could not be controlled.

19Mr. O’Brien attended several high schools. He did not, however, finish high school. He has also never been able to maintain any kind of steady employment. He has been supported by ODSP since he was 18. Although he has significant substance abuse problems, he has never completed a substance abuse program.

20Mr. O’Brien has self-reported a history of substance abuse in various interviews over the years, including large amounts of alcohol at a young age. He also used cocaine and cannabis, crystal methamphetamine, and ecstasy. He has a history of crushing and injecting his prescribed anti-psychotic and other medications. These injections have led to infections and to hospital visits, including treatment for hepatitis c.

(c) Mr. O’Brien’s Contact With The Criminal Justice System

21Since the age of 14, Mr. O’Brien’s life has been characterized by unceasing contact with the criminal justice system. His record commences in 1991 with a youth conviction for fail to comply with recognizance from Picton, Ontario. He would have been about 14 at the time of the conviction. His first adult conviction was in 1996, when he would have been 18 years old. He accumulated convictions between 1996 and 2018. He had only been released in 2021 for a short period of time when he was arrested for the index offence. The only years where he did not register a criminal conviction during that 22-year period were 1997, 2008 to 2011, and 2015-2016. He was serving sentences during all or part of those years. Between 2000 and 2026 he has only spent a total of about 8 months out of custody.

22Mr. O’Brien’s criminal record as a youth includes five convictions for failing to comply with a recognizance or disposition; one conviction for robbery; one conviction for being unlawfully at large; one conviction for uttering threats; one conviction for mischief under; one conviction for trespass by night; one conviction for assault with a weapon; three convictions for assault; one conviction for possession of property obtained by crime; one conviction for possession of a credit card obtained by crime.

23Mr. O’Brien’s adult record commences in 1996. These convictions include:

Theft under $5000 (8 convictions);
Theft over $5000;
Fail to comply with probation (4 convictions);
Fail to appear in court;
Assault (3 convictions);
Aggravated assault;
Assaulting a peace officer (6 convictions);
Assaulting a peace officer with a weapon;
Uttering threats (2 convictions);
Fraud under $5,000.00;
Obstruct peace officer (2 convictions);
Uttering a forged document;
Personation with intent;
Attempted robbery;
Escape lawful custody;
Robbery (8 convictions, including the robbery to which he pleaded guilty before me);
Committing an indictable offence while disguised (2 convictions)
Carrying a concealed weapon (2 convictions);
Extortion (2 convictions);
Mischief under $5000 (3 convictions).

24Some of these convictions have resulted in significant jail time, including penitentiary time. In 2001, Mr. O’Brien was sentenced to 30 months for robbery, consecutive to any sentence then being served. In 2004 he was convicted of robbery and sentenced to 18 months, with 235 days of pre-sentence custody noted on his record; and in 2005 he was sentenced to 10 months for extortion, consecutive to the 2004 sentences. His 2006 aggravated assault conviction resulted in a sentence of 18 months, and in 2007 he was sentenced to four years for extortion, consecutive to his other sentences. In 2014 Mr. O’Brien was sentenced to four years for robbery: 3 years and 300 days, with credit for 65 days of pre-sentence custody. Mr. O’Brien has also violated his statutory release.

25Mr. O’Brien’s long history of criminality is, obviously, connected to his long history of mental health problems. I turn to those next.

(d) Mr. O’Brien’s History Of Mental Health Assessment And Treatment

26Mr. O’Brien has a very long history of mental health hospitalizations, assessments, and attempts at treatment. These assessments arose at first out of his contact with the CCAS, then his periods of probation, and finally with correctional authorities, both federal and provincial. He has attended many times at hospital emergency departments. He has also been involuntarily admitted to hospital on several occasions. Dr. Gray recounted that history in detail in his report. I will simply summarize Mr. O’Brien’s very lengthy mental health history.

27In his youth, when in the care of the CCAS, the CCAS attempted counselling for Mr. O’Brien at his many group homes. At age 12 he was diagnosed with ADHD and prescribed Ritalin. He was hospitalized twice at age 13 and 14 for suicide attempts and behavioural disturbance. As Dr. Gray described it in his report:

There are several hundred pages of psychological assessments of Mr. O’Brien in the CCAS file from when he was a youth, almost all in response to his disruptive and aggressive behaviour. He had been diagnosed variously with conduct disorder, oppositional defiant disorder, and borderline personality disorder as a youth. He was prescribed, in addition to Ritalin, Mellaril, which is an antipsychotic that can be used off-label for aggression.

28Dr. Gray then reviewed Mr. O’Brien’s CSC records from 2001 (his first federal sentence) to 2011. He did not complete any correctional programming. He refused to participate in group programming. In fact, Mr. O’Brien has never completed any correctional programming while federally or provincially incarcerated. Some correctional facilities tried to accommodate individual programming, but Mr. O’Brien usually “got frustrated and quit.” CSC categorizes risks, such as personal/emotional, substance abuse, and associates/social interaction, in seven categories. Mr. O’Brien was at risk for all seven areas. CSC rated his motivation as “low.” He did not participate in substance abuse programming or any kind of skills programming. Each time he re-offended (or violated his statutory release or parole) and went back into custody he participated only minimally in programming. He repeatedly told Corrections staff that he did not have a problem with substance abuse. Correctional staff consistently removed him from institutional jobs – such as range cleaner or working in the mattress factory – because of repeated absences.

29During the period from 2001 to 2011 he CSC psychologists and psychiatrists interviewed Mr. O’Brien multiple times. He also had some psychological testing. Mr. O’Brien often asked for benzodiazepines, but psychiatrists were reluctant to provide them. Testing and assessments indicated that he was at a high risk to reoffend. He had admissions to psychiatric facilities from time to time.

30In 2005 Mr. O’Brien was charged with offences related to an assault on a fellow inmate. He was admitted to the Penetanguishene Mental Health Centre between July 26 and September 1, 2005. He was to undergo a court-ordered assessment by Dr. Ramshaw. She found that he was fit to stand trial and not NCR. She found (quoted from Dr. Gray’s report):

There was no evidence of major mental illness. Rather, Mr. O’Brien’s history and presentation were in keeping with a severe antisocial personality disorder, including conduct disorder during his youth. Further, he had significant psychopathic traits including quite extensive impulsivity, manipulative behaviour, lying, callousness, poor behavioural controls, early behavioural problems, failure to accept responsibility, juvenile delinquency, revocation of conditional release and criminal versatility.

31Dr. Ramshaw also diagnosed Mr. O’Brien with ADHD and noted that he had limited intelligence with low-average to borderline intellectual functioning. She also found that he was malingering in order to obtain an NCR diagnosis. A defence psychologist strongly disagreed with several aspects of Dr. Ramshaw’s findings, including her diagnosis of borderline intellectual functioning. The defence psychologist, Dr. Long, disagreed that Mr. O’Brien was a psychopathic personality and raised the possibility of fetal alcohol syndrome.

32Mr. Embry also raised the possibility of fetal alcohol syndrome in his cross-examination with Dr. Gray. Although fetal alcohol syndrome is a possible diagnosis, Dr. Gray was reluctant to make it. Fetal alcohol syndrome is not a recognized psychiatric condition in the DSM-5. Dr. Gray testified that symptoms of fetal alcohol syndrome overlap with anti-social personality disorder and ADHD. According to Dr. Gray, the problem with fetal alcohol syndrome is that it is organic to the brain – in other words, it is not something amenable to treatment.

33CSC psychologist Dr. Cotton queried the possibility of fetal alcohol syndrome. She assessed Mr. O’Brien in November 2009. Dr. Cotton did a “full battery” of tests and assessments. Dr. Gray summarized the results this way:

He scored in the bottom 2 percentile, “extremely low” on working memory, and memory functions. He had a “borderline” score, at the 8th percentile, in processing speed. Oddly, he received a “superior” score, 84th percentile, in executive functioning…. She seemed unable to explain the apparent discrepancy.

34Dr. Cotton diagnosed Mr. O’Brien with mild mental retardation and ADHD. She also stated that because of his deficits, it would be very difficult for him to participate in group programming. There was some progress in 2009, but in 2010 another CSC psychologist, Dr. Yokubynas, described him as being very hostile and confrontational in his manner. Dr. Yokubynas scored his risk as high for both general and violent recidivism.

35Mr. O’Brien was out of custody after his warrant expiry date of November 29, 2011, but was arrested and re-incarcerated on January 29, 2012, only two months later. Dr. Gray described an admission to Toronto East General Hospital on January 7, 2012:

He told the ER psychiatric nurse that “I’m suicidal. I can’t cope with being on the outside.” He admitted to daily use of crack cocaine for the last few days. He was thinking of suicide or “perhaps committing a major crime to return to prison ‘cause I can’t cope, this is too hard.”

36After release, he went to several hospitals with suicidal thoughts until admitted on a Form 1. He was then arrested and incarcerated for the next 7 months. After release, he was again in and out of emergency rooms and admitted from time to time, dealing with infections from intravenous drug use as well as psychiatric issues. He told a psychiatrist that he was “not coping with living on the outside”. He also told a social worker that the routine of jail was comforting as he always knew when he was getting his meals and what the schedule was. He continually expressed and then denied suicidal thoughts. He went back into custody on December 16, 2012. He had another court-ordered assessment in August 2013. There was discussion, but no conclusion, about the presence of psychotic symptoms. There was some observation of malingering. In October 2013, however, he was admitted to St. Lawrence Valley Correctional Institute, a psychiatric facility. He told the admitting psychiatrist that it is hard to cope with life in the community, having been out of custody for only 6 of the previous 13 years. He also disclosed that he had auditory hallucinations, but they had improved with anti-psychotic medication. The admitting psychiatrist was also skeptical that he had experienced auditory hallucinations. She did not think that he had bipolar disorder, but she could not rule out a psychotic disorder. He was on a heavy dose of anti-psychotic medication at the time.

37Throughout this period Mr. O’Brien demanded several medications, including Wellbutrin, which was denied because of the potential for abuse. He continued to be diagnosed with ADHD; substance-induced psychosis; substance abuse disorders; mild mental retardation; and personality disorder antisocial/borderline traits.

38Mr. O’Brien was released again on March 9, 2014, but was back in hospital on a Form 1 within two days. He again had multiple hospital visits and another Form 1. He was back in custody again on May 5, 2014. Between 2014 and 2017 he was again federally incarcerated. He again did not complete any treatment programs. A new assessment by CSC psychologists put him at a high risk for general and violent recidivism, with his “most salient risk factor appears to be substance dependence, lack of prosocial supports, impulsivity, poor emotion regulation and coping skills, lack of employment and/or interest in obtaining same, and antisocial attitude/orientation.” He had not improved in any of the seven categories of risk and either continued to refuse to attend treatment or was placed in segregation after misconducts and was unable to attend treatment.

39On January 3, 2017, Mr. O’Brien was granted statutory release to a halfway house. He had one good appointment with a psychologist. A subsequent meeting with a psychiatrist did not go well. The psychiatrist, Dr. Dickey, suggested tapering his medication. Dr. Dickey also wrote “I doubt this individual would be able to last at the halfway house setting and I have some concern as to his potential for aggressivity or violence.” Mr. O’Brien met Dr. Dickey on January 24, 2017. He was taken back into federal custody the same day.

40Dr. Gray noted that after 2017, Mr. O’Brien deteriorated significantly. He wrote:

What followed from that time to the present has been significant disorganized behaviour, thought disorder, and a major decline in his level of self-care. He was repeatedly smearing his feces, sometimes eating his own feces, dishevelled, and talking or shouting to himself. There were brief periods of remission of these symptoms, at which time he continued to engage in non-psychotic disruptive behaviours such as verbal aggression if his demands were not met, and threats to staff.

41Mr. O’Brien continued to be transferred to psychiatric institutions. He indicated that he was hearing voices. In 2017 he was assessed again at Waypoint to determine if he was NCR. Dr. Dickey noted that he did appear to have a major mental illness. He was released on statutory release again on May 3, 2018, but went back into custody on May 11, 2018. He continued to exhibit bizarre behaviour, to have signs of malingering, but was highly manipulative to try to get what he wanted, usually medication in order to crush it for ingesting. He showed some signs of improvement in preparation for his statutory release in October 2018 and his warrant expiry date in December 2018. Unfortunately, he refused to participate in assessments or other preparation that he needed for re-integration.

42Mr. O’Brien was released on December 24, 2018, his warrant expiry date. Shortly after that he began to present, again, at emergency rooms. He presented at one hospital on January 4, 2019. He told staff that he was hearing voices. He had to be restrained due to his aggressive behaviour. He presented the next day at a different hospital but when police approached him, he was holding a meat cleaver. He was placed on a Form 1, but it was cancelled and he was released. Unfortunately, he committed a series of robberies and was back in custody on January 22, 2019.

43While in custody, Mr. O’Brien constantly asked for prescriptions of Bupropion and Quetiapine, and sometimes Ritalin. Bupropion’s brand name is Wellbutrin, and it is an anti-depressant. Quetiapine’s brand name is Seroquel, and it is an anti-psychotic used to treat schizophrenia, bipolar disorder, and depressive disorders. He once again asked for these medications. CSC officers noted that he had been hoarding some of these medications. Psychiatrists often refused to agree to his request for more of these medications as it was feared that Mr. O’Brien was abusing them.

44Another assessment of Mr. O’Brien was ordered in relation to his new robbery charges. Dr. Ferencz assessed him between June 5 and June 17, 2019, to determine whether he was NCR. Dr. Ferencz found that Mr. O’Brien’s attempts to exhibit odd behaviour were the result of malingering because he wanted an NCR finding. He diagnosed Mr. O’Brien with antisocial personality disorder and polysubstance use disorder. He found that any suggestion of mental illness was feigned to avoid responsibility.

45Dr. Gray detailed the numerous mental health interventions after 2020 in his report. In August 2020 an assessment of fitness to stand trial was ordered by the court. He was found fit. He continued to ask for increases in his medications. He appeared to have auditory hallucinations and demanded an increase in his dosage of Bupropion. Some of his medications were again cut off due to hoarding. Thereafter began a long series of psychiatric examinations where Mr. O’Brien would ask for increases in his medication and showed continued disintegration. He continued to appear to have auditory hallucinations, threatened suicide, smeared feces, and exhibited “pronounced thought disorder”. A third assessment in relation to his 2019 charges was ordered, again into the possibility of NCR. This time, Mr O’Brien took the position that he did not want to be found NCR.

46It was during this assessment, however, in 2021 that Mr. O’Brien was diagnosed with a primary psychotic disorder. Dr. Choptiany found, based on bizarre behaviour and auditory hallucinations, that Mr. O’Brien had “unspecified schizophrenia spectrum and other psychotic disorder, substance abuse disorder (amphetamine and opioid), and antisocial personality disorder.” Because his robberies were goal directed and required some planning, Dr. Choptiany again found that Mr. O’Brien was not NCR.

47Mr. O’Brien was released on November 23, 2021. He was brought to a hospital emergency room as he was found mumbling to himself and having what appeared to be auditory hallucinations on November 26, 2021. He committed the index offence on November 27, 2021. He has been in custody ever since. His behaviour conformed to the same pattern as in the past: covered in or smearing feces; attempting to get more medications; hearing voices; lack of cooperation; sometimes voicing suicidal thoughts; and manipulative behaviour. In March 2022, Mr. O’Brien was subject to a treatment order and another fitness assessment. Dr. Ali found that he was fit to stand trial, but also diagnosed Mr. O’Brien with unspecified schizophrenia disorder, delusional thought process, and bizarre and aggressive behaviour, and likely substance abuse disorder. He took injectable anti-psychotic medication but then refused it and requested Quetiapine. He thereafter refused the injectable and began to deteriorate until he again agreed to take it in September 2022. He continued to be admitted to hospitals on a Form 1, reject, and then accept injectable medications. As of the time of Dr. Gray’s assessment, Mr. O’Brien was compliant with his injectable medication.

(e) Dr. Gray’s Diagnosis

48Mr. O’Brien repeatedly refused to meet with Dr. Gray. As a result, Dr. Gray formed his diagnosis based on an exhaustive review of extensive medical records. He stated in his report, and testified, that he had enough material – some 15,000 pages – to assign a psychiatric diagnosis.

49Dr. Gray opined that Mr. O’Brien meets the criteria for the following:

Antisocial personality disorder;
Stimulant use disorder, severe, in partial remission in a controlled environment;
Schizophrenia;
Intellectual disability, mild severity.
Signs of attention deficit hyperactivity disorder.

50The DSM-5 defines anti-social personality disorder as a pervasive pattern of disregard for, and violation of, the rights of others occurring since the age of 15. The diagnosis requires that three of seven criteria be established. These are: “failure to conform to social norms with respect to lawful behaviours as indicated by repeatedly performing acts that are grounds for arrest; impulsivity; irresponsibility; irritability and aggressiveness; lack of empathy; deceitfulness; and reckless disregard for the safety of self or others.” Dr. Gray found that Mr. O’Brien exhibited all of them strongly, but that there was less evidence of a reckless disregard for the safety of self or others, although still some evidence to support that symptom.

51The DSM-5 requires that a person meet 2 of the 11 listed criteria for stimulant use disorder, severe, in partial remission in controlled environment. Dr. Gray found that Mr. O’Brien meets 8 of the criteria. Some of the criteria include recurring stimulant use; using a great deal of time to obtain drugs, use them, and recover; unsuccessful efforts to cut down; and use of substances despite deleterious mental health effects. The disorder is severe because Mr. O’Brien meets 6 or more of the criteria.

52The DSM-5 requires that a person meet two of five symptoms for schizophrenia. They are delusions; hallucinations; disorganized speech; grossly disorganized or catatonic behaviour; and negative symptoms such as diminished emotional expression or avolition. Dr. Gray went on:

There also needs to be a marked decrease in the level of functioning in one or more major areas such as work, interpersonal relations or self care for a significant portion of time since the onset of the disturbance. The diagnosis also requires that continued signs of the disturbance persist for at least six months, which includes at least one moth of two of the five symptoms. The disturbance cannot be directly attributable to the physiological effects of a substance or another medical condition.

53Dr. Gray noted that Mr. O’Brien consistently reported auditory hallucinations for many years. He also demonstrated disorganized speech and disorganized behaviour. He has also shown avolition by remaining unresponsive in his cell for lengthy periods of time. Although Mr. O’Brien appears to have been older than the usual 15-25 age range when he began hearing voices, Dr. Gray noted that he showed symptoms but that they were diagnosed as malingering for the purpose of an NCR assessment. His view was that mental health professionals were likely distracted by other problems and mis-diagnosed him. I accept Dr. Gray’s evidence on this point and his diagnosis.

54Dr. Gray agreed with past assessments that Mr. O’Brien had cognitive deficits and that he was in the “extremely low” range of overall intelligence. Corrections staff had tried to conduct a functional assessment but Mr. O’Brien’s behaviour and resistance made it impossible for them to do so. Given Mr. O’Brien’s lifelong inability to live independently, hold a job, or manage his money, he clearly has a significant degree of functional impairment. Dr. Gray also noted ADHD. Mr. O’Brien’s first formal diagnosis of ADHD was as a young person. The diagnosis has been consistent and has not changed over the years.

55I accept Dr. Gray’s diagnoses. They are based on an extensive review of the records. It appears that Dr. Gray is the first assessor to have access to all the records, in one place, including Mr. O’Brien’s youth records.

(f) Dr. Gray’s Assessment of Risk

56Dr. Gray had to use assessment tools without an interview of Mr. O’Brien, as Mr. O’Brien refused to meet with him. He conducted the Psychopathology Checklist – Revised (“PCL-R”). The PCL-R roughly measures psychopathy. Based on his review of collateral sources, Dr. Gray assigned a PCL-R score of 29. That put in him the 79.5 percentile of North American male offenders, but it is much higher than the average offender. The average score for male offenders is 22-23. Any score of 30 or over indicates psychopathy. There are two sub-scores. Mr. O’Brien was at the 57.1 percentile for interpersonal and affective factors; and at the 100 percentiles for lifestyle and antisocial factors. Dr. Gray noted that other psychologists and psychiatrists had assessed Mr. O’Brien at similarly high scores: a 2001 risk assessment scored him at 25; a 2009 risk assessment at 29; and a 2014 assessment scored him at 28.

57Dr. Gray also conducted an actuarial assessment called the Violence Risk Appraisal Guide (VRAG). He scored Mr. O’Brien at +31, which puts him at the highest of the 9 ascending risk categories with a very high risk of re-offending. Actuarially, Dr. Gray said this:

76% of offenders in the VRAG-R study population, who had similar risk scores to Mr. O’Brien on this instrument, reoffended with a violent offence within five years of their release to the community. 90% of offenders in the study population who had scores similar to Mr. O’Brien reoffended with a violent offence within 15 years of their release from incarceration. His score of +31 is higher than 95% of those offenders in the study population assessed with this instrument.

58Dr. Gray noted that Mr. O’Brien’s schizophrenia is amenable to treatment with anti-psychotics. He has taken the injectable anti-psychotic Paliperidone (brand name Sustenna) but his compliance and willingness to take it has been inconsistent and he has refused to take it many times.

59I accept Dr. Gray’s evidence that Mr. O’Brien is at a very high risk of re-offending.

IV. ISSUES

60The main purpose of dangerous offender legislation is the protection of the public from future violent offending. The concept behind the legislation is that the offender is separated from the public and receives treatment, facilitating reintegration if the offender is treated: R. v. Jones, 1994 85 (SCC), [1994] 2 S.C.R. 229 at para. 124. As part of the sentencing process, all sentencing purposes and principles play a role, but they are generally subordinate to the purpose of protecting the public: R. v. Johnson, 2003 SCC 46 at para. 23. The over-arching purpose is not punitive: R. v. Smith, 2023 ONCA 575 at para. 17.

61The onus is on the Crown to prove beyond a reasonable doubt that an offender meets the criteria to be a dangerous offender. Pursuant to s. 753(1) of the Criminal Code, where a person is convicted of a serious personal injury offence, the court shall find him or her to be a dangerous offender where the offender “constitutes a threat to the life, safety or physical or mental well-being of other persons.” In other words, if the court finds that the criteria are met, there is no discretion. The offender must be designated a dangerous offender subject to s. 753(4) and 753(4.1) of the Criminal Code: R. v. Boutilier, 2017 SCC 63 at para. 20.

62The hearing is a two-stage process. At the first stage the court determines whether the offender is a dangerous offender. There is no discretion in the first stage. As noted, if the court finds the offender to meet the statutory criteria, the offender must be designated as a dangerous offender. At the second stage, there is some discretion in relation to the penalty imposed. The court must impose an indeterminate period of incarceration unless the court is satisfied that there is a reasonable expectation that a lesser measure will adequately protect the public: R. v. Boutilier at para. 20; Criminal Code, s. 753(4.1).

63There are four routes to finding an offender to be a dangerous offender during this first stage. The first route, pursuant to s. 753(1)(a)(i) requires the finding to be made where the evidence establishes:

64A 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.

65Section 753(1)(a)(ii) sets out the second route. Again, the finding is required to be made where the evidence establishes:

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.

66The third route involves a finding where the offence is of a brutal nature. The Crown is not relying on that route. The fourth route involves sexual offences, which does not apply in this situation.

67I frame the questions this way:

(a) Does Mr. O’Brien constitute a threat to the life, safety, or physical or mental well-being of other persons on the basis of a pattern of repetitive behaviour showing a failure to restrain his behaviour and a likelihood of causing death, injury, severe psychological damage through failure to restrain his or her behaviour? (Criminal Code, s. 753(1)(a)(i)).

(b) Does Mr. O’Brien constitute a threat to the life, safety, or physical or mental well-being of other persons on the basis of a pattern of persistent aggressive behaviour, showing substantial indifference respecting the reasonably foreseeable consequences to other persons of his or her behaviour? (Criminal Code, s. 753(1)(a)(ii)).

(c) Is there evidence that a lesser measure than an indeterminate sentence will adequately protect the public against the commission by the offender of murder or a serious personal injury offence? (Criminal Code, s. 753(4), 753(4.1)).

68If the answer is “yes” to either question (a) or question (b) (or both), then I must find Mr. O’Brien to be a dangerous offender and impose an indeterminate period of incarceration unless question (c) applies. If I find that the answer to question (c) is “yes”, then I must impose either a long-term supervision order not exceeding ten years or impose a sentence. If I find that the answer is “yes” to either question (a) or question (b) (or both) and the answer to question (c) is “no”, then I must find that Mr. O’Brien is a dangerous offender and sentence him to an indeterminate period of incarceration.

69If the answer is “no” to questions (a), (b), then I must find that Mr. O’Brien is not a dangerous offender. I may then find Mr. O’Brien to be a long-term offender or hold another hearing to determine if he is a long-term offender. Alternatively, I may impose a sentence.

70As will become evident, my answer to questions (a) and (b) is “yes and my answer to question (c) is “no”. Mr. O’Brien is a dangerous offender. He is sentenced to an indeterminate period of incarceration.

V. ANALYSIS

(a) Is Mr. O’Brien A Threat Based On A Pattern Of Repetitive Behaviour?

71 Section 753(1)(a)(i) of the Criminal Code states:

753 (1) … the court shall find the offender to be a dangerous offender if it is satisfied

(a) that the offence for which the offender has been convicted is a serious personal injury offence described in paragraph (a) of the definition of that expression in section 752 and the offender constitutes a threat to the life, safety or physical or mental well-being of other persons on the basis of 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

72There is no doubt that robbery is a serious personal injury offence: R. v. Cassie, 2020 ONSC 1939 at para. 27.

73Although there is no evidence that Mr. O’Brien ever had a gun or a bomb during the robbery, I conclude that the threat was sufficient to put the robbery in the category of a serious personal injury offence. Indeed, many of Mr. O’Brien’s offences have not involved actual physical violence – but many, such as the assaults, have. Some of his most serious offences, such as the robberies, have involved significant psychological harm. As the Supreme Court explained in R. v. Steele, 2014 SCC 61 at paras. 5 and 23, a threat of violence that is enough to ground a conviction for robbery is “the use of violence against another person” pursuant to the Criminal Code. In Steele, the offender did the same thing that Mr. O’Brien has often done: he approached a bank teller, told her it was a robbery, and told her he had a gun. Nobody observed a gun. That was sufficient for a finding.

74The focus here is on prior behaviour, not just prior offences. What is critical are the elements of similarity: R. v. Smith at para. 25; R. v. Langevin (1984), 1996 18768 (NB CA), 111 C.C.C. (3d) 336, [1984] 1914 (Ont.C.A.) at para. 29. Similarities in behaviour can constitute a pattern of repetitive behaviour: R. v. Gibson, 2021 ONCA 530 at para. 224. In that case, Watt J.A. agreed with the decision of the Saskatchewan Court of Appeal in R. v. Knife, 2015 SKCA 82. That court stated at para. 67:

There are two main ways of identifying this repetitive behaviour: as stated in Neve at para. 111, there may be similarities in the types of offences, or similarities in the degree of violence used. For example, an offender with a history of committing aggravated assaults has necessarily demonstrated a repetition of violent behaviour, as a high degree of violence is implied in the very nature of aggravated assault. Rosenberg J.A. in the Szostak decision of the Ontario Court of Appeal, at para. 63, agreed with Neve stating “Similarity… can be found not only in the types of offences but also in the degree of violence or aggression threatened or inflicted on the victims” (Neve at para. 113).

75In my respectful view, it is unassailable that Mr. O’Brien has shown a pattern of repetitive behaviour inflicting severe psychological harm to victims, through a failure to restrain his behaviour. The pattern of bank robberies is incredibly similar: Mr. O’Brien walks into a bank, demands cash, indicates that he has a weapon or a bomb, and then leaves. He has done the exact same thing multiple times, and usually within a short period after release from custody. He has not grown out of this pattern of offending. As a young offender, he was convicted of one count of robbery. As an adult, however, he has been convicted of multiple counts of robbery or attempted robbery, but on several occasions the facts on of other robberies to which he did not plead were read in and accepted. I do not need to go through them all. Other judges – and I agree with them – have noted that he is almost certain to commit offences when released. In the last 26 years, Mr. O’Brien has not been able to stay out of custody for – at most – three months before committing another robbery or other offence. Victim impact statements speak to the harm. It is a mistake to think that simply because Mr. O’Brien has not had a bomb or a gun does not mean that the robbery is not frightening to the victims, and a cause of psychological harm.

76Mr. O’Brien has also been convicted of other violent assaults, including aggravated assault and numerous assaults on police officers or correctional officers. Many of these violent offences have been committed while in custody. He has also accumulated many institutional misconducts, although I give those much less weight – they do not (at least until recently) require a finding of proof on a criminal standard; and they may arise out of the difficult conditions that are often found in custodial settings.

77Dr. Gray listed the periods where Mr. O’Brien was able to stay out of custody after 2000, when he received a sentence for robbery:

Released from custody on statutory release July 17, 2003; arrested on July 18, 2003, for robbery.
Out of custody from November 29, 2011, to January 29, 2012 (although he was hospitalized on several occasions during that time).
Out of custody from March 9, 2014, to May 5, 2014 (again, he was hospitalized on several occasions during that time).
Out of custody from January 3, 2017, to January 24, 2017, on statutory release;
Out of custody from May 3, 2018, to May 11, 2018, on statutory release;
Out of custody from October 9, 2018, to October 12, 2018, on statutory release;
Out of custody from December 24, 2018, to January 22, 2018, on statutory release;
Out of custody from November 23, 2021, to November 27, 2021, on statutory release when he was arrested for the index offence.

78Again, while in custody (and out) Mr. O’Brien has also committed other violent offences such as assaults, an aggravated assault, and extortion. In fact, his lengthy record discloses four convictions for assault (or assault with a weapon) as a youth and eleven convictions for various types of assaults (including assaults of peace officers, with a weapon, and aggravated assault) as an adult. Even ignoring the youth convictions would still generate a pattern as an adult.

79The robberies have inflicted severe psychological damage on other persons. Victim impact statements attest to that. Some of the other offences have also caused physical injuries. Unfortunately, I am also forced to conclude that Mr. O’Brien is intractable. Intractability is not a necessary element for finding a person to be a dangerous offender. Rather, I agree with this statement by my colleague Corrick J. in R. v. Inacio, 2018 ONSC 6617 at para. 172:

Justice Greene of the Ontario Court of Justice recently considered this issue in R. v. Broadfoot 2018 ONCJ 215. She concluded that intractability at the designation stage relates to whether the conduct can be treated. If the court finds that the conduct is intractable, the question at the penalty stage is how to manage that conduct: Broadfoot, at para. 77. Justice Rutherford adopted this analysis in the case of R. v. Hoshal 2018 ONCJ 497. The analysis makes sense to me, and I adopt it.

80See also R. v. Windebank, 2023 ONSC 4809 at para. 124 where my colleague Kelly J. adopted Corrick J.’s statement; and R. v. Boutilier at para. 32.

81An example of Mr. O’Brien’s intractability – and frankly it has not changed – was noted by Dr. Gray in his report. Dr. Gray stated:

In the parole casework log, he again refused programming as indicated in an April 19, 2002 note. He said he did not want to go to a half-way house, and if he did, “he would come right back to jail until his WED [Warrant Expiry Date]”.

82Justice Hill exhaustively listed the factors in R. v. D.B., 2015 ONSC 5900 at para. 199. Although he did so at the penalty stage, they are still relevant at the designation stage. I apply the key ones here:

Mr. O’Brien has refused to cooperate or engage with the process;
Mr. O’Brien has consistently refused treatment or failed to take advantage of treatment opportunities;
Mr. O’Brien has a very mixed record in terms of his compliance with prior treatment programs. He also has a very mixed record in terms of compliance with medication regimes, although he has been more willing to take injectable anti-psychotic medications in the last year;
Mr. O’Brien has demonstrated absolutely no motivation in the past to take group treatment, and very limited motivation to take individual treatment. He has never completed any treatment programs other than one anger management program as a young offender;
While Mr. O’Brien’s schizophrenia could be treated in the future, that would require a significant shift in his attitude;
Regrettably, although Mr. O’Brien has consistently pleaded guilty, there is little evidence of genuine remorse. In fact, he has explicitly stated on occasion that he has committed offences even for the purpose of getting back into custody.

83Unfortunately, Mr. O’Brien’s intellectual disability and his ADHD make it very difficult for him to participate in programs. His low level of cognitive functioning has contributed to this problem.

84Dr. Gray also reviewed the question of intractability, recognizing that it is a legal, not a medical concept. Mr. O’Brien’s diagnosis of anti-social personality disorder drives much of his criminal behaviour. Personality disorders involve “entrenched, difficult to treat character traits” that cause problems for the majority of a person’s life. His disorder, according to Dr. Gray, has been the major cause of his offending. His inability to control his anger and regulate his emotions have resulted in impulsive decisions and poorly thought-out criminal actions. His severe stimulant use disorder has also played a major role. He has found it very difficult to deal with this disorder and it is also a major driver of his offending.

85The assessment of future risk must be linked to the past criminal behaviour: R. v. Knife, at paras. 61-62. Given Mr. O’Brien’s consistent offending, there is no doubt that the link exists. Virtually all of the actuarial and structured judgment tools point in that direction. Dr. Gray’s assessment was that he was at an extremely high risk for re-offending. I would go further: if Mr. O’Brien is released, it is virtually certain that he will re-offend, re-offend violently, and re-offend in very short order.

86I am satisfied beyond a reasonable doubt that Mr. O’Brien meets the criteria set out in s. 753(1)(a)(i) of the Criminal Code.

(b) Is Mr. O’Brien A Threat Based On A Pattern Of Aggressive Behaviour?

87 Section 753(1)(a)(ii) of the Criminal Code states:

753 (1) … the court shall find the offender to be a dangerous offender if it is satisfied

(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…

88In R. v. Smith, Thorburn J.A. stated at para. 37 that to fulfill this criteria there must be:

A pattern of behaviour;
Involving persistent acts of aggression causing serious harm and demonstrating a substantial degree of indifference to the consequences of the offenders actions;
That create a serious risk of ongoing harm to the public.

89I agree with the Saskatchewan Court of Appeal’s comment, excerpted in the Crown’s written material, analyzing the distinctions between s. 753(1)(a)(i) and (ii) in R. v. Montgrand, 2017 SKCA 49, 352 C.C.C (3d) 485 at para. 21:

Although the patterns contemplated by ss. 753(1)(a)(i) and (ii) overlap, each is distinct. Section 753(1)(a)(i), as noted, requires a pattern of repetitive behaviour; whereas, s. 753(1)(a)(ii) requires a pattern of persistent aggressive behaviour. While the behaviour covered by the former is broader than the latter, the pattern under s. 753(1)(a)(i) must itself establish a likelihood or probability of reoffending in a certain way with a certain result. By contrast, s. 753(1)(a)(ii) does not refer to likelihood or probability; rather, the pattern contemplated must show "a substantial degree of indifference on the part of the offender respecting the reasonably foreseeable consequences to other persons of his or her behaviour." This calls for an analysis of the subjective state of mind of the offender. Where the offender does not testify, it must be conducted on the objective evidence adduced at the sentencing hearing.

90There is no question that Mr. O’Brien has engaged in a pattern of aggressive behaviour. He has multiple convictions for assault and other violent behaviour on his record. He has accumulated multiple institutional misconducts. His personal behaviour has been hostile and aggressive. It has been noted by CSC personnel and noted in files. It has been noticeable even in court. I have little trouble finding that he fulfills the requirement of a repetitive behaviour.

91The Crown must also show that the offender’s behaviour reflects indifference to the consequences of his actions to others: R. v. Wong, 2023 ONCA 118 at para. 51. In the trial decision in that case (R. v. Wong, 2016 ONSC 6362), McWatt J. (as she then was) stated at para. 224:

In examining whether Mr. Wong's conduct demonstrates indifference, his attitude must be examined more generally. A demonstration of indifference which is limited to the time at which the offence was committed is not sufficient. A broader examination of the offender's personality is required in order to determine if the offender lacks compassion towards others. The Crown must demonstrate that the offender has a conscious, but uncaring awareness of causing harm to others and that this has occurred over a long period, involving frequent acts with significant consequences. Expert evidence can be drawn upon in deciding whether the previous acts of aggressive conduct demonstrate the requisite indifference.

92In his report, Dr. Gray noted that Mr. O’Brien’s “overall disregard for the rights of others, and seeming inability to empathize with those affected, allowed Mr. O’Brien to continue in that offending pattern throughout his life despite legal sanction.”

93Mr. O’Brien, although he has usually pleaded guilty, has rarely displayed empathy for the victims of his crimes. He did not do so during the sentencing hearing for the index offence. I was provided with a number of transcripts. Not all of these transcripts indicate what happened when Mr. O’Brien was asked if he wished to address the court before sentencing. Some do, however, and in none does he ever indicate any expressions of remorse or apology – except on one occasion, where he backtracked. In that one case Mr. O’Brien did apologize fir an aggravated assault in the penitentiary – but he then backtracked and claimed he had nothing to do with it. These are the transcripts I do have:

During his sentencing on March 8, 2004, for robbery before Justice Shamai, Mr. O’Brien stated that he did not want to “live this way anymore.” That appears to have been his only comment on the offence.
On January 20, 2005, Justice Ormston of the Ontario Court of Justice sentenced Mr. O’Brien for extortion. When asked if there was anything he wished to say before being sentenced, he replied “no, your honour”.
On May 16, 2006, Justice Marchand of the Superior Court sentenced Mr. O’Brien on charges of aggravated assault and utter threats after pleading guilty. He did apologize to the victim in court and denied making any racial comments. He also said that he was not on his proper medication, which caused him to commit the offence. He indicated that he would respect the decision of the court. At the end of the sentencing, however, he stated that he “didn’t do none of this” and just pleaded guilty because he was tired of waiting around the courthouse.
During peace bond proceedings before Justice Bhaba of the Ontario Court of Justice on November 29, 2011, Mr. O’Brien’s only interest was in dealing with the matter so he would not have to wait. He expressed no sympathy for the victim.
On June 19, 2014, Mr. O’Brien pleaded guilty to robbery before Justice Dobney in the Ontario Court of Justice. When asked by the judge if he had anything to say before being sentenced, he indicated he did not. He simply wanted to be sent to Ontario Shores.
On November 30, 2017, Mr. O’Brien pleaded guilty to multiple counts of assault before Justice Griffen of the Ontario Court of Justice. The assaults involved federal correctional officers. In a very long discussion with the sentencing judge, Mr. O’Brien did not express any concerns about the victims.
On February 12, 2018, Mr. O’Brien was before Justice Griffen again for similar offences. He had another long discussion with the sentencing judge. That discussion also did not include any concern for the victims.
On November 23, 2021, Mr. O’Brien pleaded guilty before Justice Goodman of the Superior Court to multiple counts of robbery and committing an indictable offence with his face masked. When asked if he had anything to say before being sentenced, Mr. O’Brien had several complaints and indicated that he wanted to receive a sentence of time served – and if he did not then he was going to strike his plea. He did not have anything to say about the victims, who were terrorized.

94I recognize that an accused person is under no obligation to say anything at a sentencing hearing, and certainly under no obligation to express remorse or apologize. A guilty plea, at least in theory, does that and Mr. O’Brien almost always pleads guilty. No offender is to be punished for keeping silent or failing to express empathy or sympathy. What is important here is that the failure to ever express any empathy is consistent with Dr. Gray’s diagnosis of a personality disorder and the observation that he has very limited insight.

95I must note that Dr. Gray also noted in his report that:

Mr. O’Brien has shown limited insight into his risk factors over the years. At times, he has admitted that his use of substances is highly correlated with his offences. However, despite this periodic recognition of one of his main problems, he very quickly returns to the pattern when out in the community. It is possible his voicing a recognition of addictions as one of his problems is a form of impression management, as it may result in a lighter sentence. I note that similarly, he often pleads guilty to his offences and then admits shortly afterwards that he just “wanted to get it over with” and didn’t believe that he was actually guilty. It is also a form of lack of acceptance of responsibility in that he blames substances for his offending behaviour.

96I am satisfied beyond a reasonable doubt that Mr. O’Brien meets the criteria set out in s. 753(1)(a)(ii) of the Criminal Code.

(c) Will A Measure Less Than An Indeterminate Sentence Protect The Public?

97 Sections 753(4) and 753(4.1) of the Criminal Code state:

753 (4) If the court finds an offender to be a dangerous offender, it shall

(a) impose a sentence of detention in a penitentiary for an indeterminate period;

(b) impose a sentence for the offence for which the offender has been convicted — which must be a minimum punishment of imprisonment for a term of two years — and order that the offender be subject to long-term supervision for a period that does not exceed 10 years; or

753 (4.1) The court shall impose a sentence of detention in a penitentiary for an indeterminate period unless it is satisfied by the evidence adduced during the hearing of the application that there is a reasonable expectation that a lesser measure under paragraph (4)(b) or (c) will adequately protect the public against the commission by the offender of murder or a serious personal injury offence.

98Thus, the court is required to impose an indeterminate sentence unless it is satisfied that a lesser measure will protect the public. If so, the court may impose a determinate sentence and a long-term supervision order; or it may simply impose a sentence.

99The requirements of s. 753(1)(a) have been met. Accordingly, Mr. O’Brien is declared a dangerous offender. The next question is whether I am satisfied that a lesser measure will adequately protect the public. The Supreme Court set out the analytical steps in R. v. Boutilier at para. 70:

First, if the court is satisfied that a conventional sentence, which may include a period of probation, if available in law, will adequately protect the public against the commission of murder or a serious personal injury offence, then that sentence must be imposed. If the court is not satisfied that this is the case, then it must proceed to a second assessment and determine whether it is satisfied that a conventional sentence of a minimum of 2 years of imprisonment, followed by a long-term supervision order for a period that does not exceed 10 years, will adequately protect the public against the commission by the offender of murder or a serious personal injury offence. If the answer is "yes", then that sentence must be imposed. If the answer is "no", then the court must proceed to the third step and impose a detention in a penitentiary for an indeterminate period of time.

100For the purposes of the penalty phase, I come back to the question of intractability: R. v. Broadfoot; R. v. Windebank. For the reasons I have already mentioned, I find that Mr. O’Brien is, unfortunately, something of a poster-child for intractability. Although he has lately taken his injectable medication, and his schizophrenia can be controlled with medication, his long history of abusing his medications, refusing treatment, and engaging in criminal and anti-social behaviour militate in favour of finding that he is intractable. As Dr. Gray observed, it is highly unlikely that he is going to change his behaviour.

101Dr. Gray also observed:

A final issue is Mr. O’Brien’s highly elevated score on the PCL-R instrument, which is just short of the threshold of psychopathy. I noted that experienced CSC psychologist, Dr. Yokubynas arrived at the same score as mine, and a second CSC psychologist more recently arrived at a similar high score. High scores on this instrument, especially of 25 or above, are correlated with a higher risk of general and violent offending, and a lower probability of successful treatment. His psychopathic traits would pose additional psychiatric evidence in favour of the legal test of “intractability” as I understand the concept.

102With those observations in mind, I turn to the Boutilier criteria.

103Applying the first criteria, I am not satisfied that a conventional sentence will adequately protect the public. If the criminal standard of proof were required, I would find beyond a reasonable doubt that Mr. O’Brien will commit a serious personal injury offence within months, if not days, of his release from custody. That is my observation as a sentencing judge applying the maxim that the best predictor of future performance is past behaviour. It was also the observation of other sentencing judges. Unfortunately, they were proven right. It was also Dr. Gray’s observation as a forensic psychiatrist.

104Mr. O’Brien himself has frequently stated that he cannot handle life on the outside and he will commit offences so that he can be re-incarcerated. Frankly, it is so obvious that a conventional sentence would be inadequate that no further analysis is required.

105I think it is also obvious that a long-term supervision order would not adequately protect the public. Mr. O’Brien has never completed a treatment program, other than one custodial anger management program as a young offender. Indeed, he usually refuses to participate in any treatment programs. Part of that is due to his anti-social personality disorder, which remains very challenging to treat.

106Dr. Gray also noted that given his diagnosis of schizophrenia, and his long history of non-compliance (or limited compliance) with medication regimes, there is a “reasonably good chance” that he would go back into custody or be hospitalized if released. Dr. Gray also noted that Mr. O’Brien has been unable to remain stable in the community since 2000. He keeps going back into custody, and when out of custody he is frequently hospitalized. Dr. Gray observed that even within the structured setting of a half-way house, he has been unable to stay out of custody.

107Dr. Gray’s view was that:

If subject to a long-term supervision order, the most likely outcome in my opinion would be rapid and frequent breaches of conditions and return to custody, thus protecting the community by limiting his access.

… the prospect of successful treatment of Mr. O’Brien’s risk factors for violence is extremely low.

In summary, in my opinion I am not able to foresee any interventions that would result in successfully mitigating Mr. O’Brien’s risk of committing another similar reoffence that is likely to cause psychological harm to potential victims in the community.

108I agree with this observation based on all the evidence before me.

109There is always a danger that a trier of fact will be overwhelmed by the expertise and eloquence of an expert witness, and delegate the judicial decision-making function that properly belongs to the jury or the judge. In this case, while I give Dr. Gray’s opinion weight, I think the evidence is simply overwhelming that Mr. O’Brien fits the criteria for a dangerous offender and that there are no measures that would adequately protect the public from another serious personal injury offence.

(d) Conclusion: A Dangerous Offender Designation Is Warranted

110I conclude that Mr. O’Brien should be designated as a dangerous offender. He remains at a high risk of recidivism. All the evidence suggests that he will commit a violent crime within a very short period of release. He will do it to get back into jail because he cannot handle the outside world, or he will do it because he cannot help himself and criminality is all he knows. It is tragic because it is almost as if our society has given up on him. But the primary sentencing principle in a dangerous offender situation is protection of the public. I am compelled to reach this conclusion based on the law and the evidence.

VI. DISPOSITION

111Mr. O’Brien is declared a dangerous offender pursuant to s. 753(1)(a) of the Criminal Code. He is sentenced to an indeterminate period in the penitentiary pursuant to s. 753(4)(a) of the Criminal Code. This is an extremely regrettable result. As I stated at the beginning, Mr. O’Brien is one of those people who was born into a situation where he faced tremendous obstacles. It is unfortunate and tragic, but my duty on this application is to apply the law and to protect the public without sympathy, prejudice or favour.

R.F. Goldstein J.

Released: May 20, 2026