ONTARIO COURT OF JUSTICE

CITATION: R. v. Darling, 2026 ONCJ 461

DATE: 2026-08-04

Toronto Region

BETWEEN:

HIS MAJESTY THE KING

— AND —

JAMEILAH DARLING

Before Justice J. Bliss

Heard on October 8, 2025, December 19, 2025, and June 8, 2026

Reasons for Sentence released on August 4, 2026

S. Scratch............................................................................................. counsel for the Crown

I. Gavran........................................................... counsel for the accused Jameilah Darling

BLISS J.:

[1] On June 19, 2022, Juqjuan Darling was alleged to have left a loaded firearm in the washroom of a downtown Toronto restaurant which led to him being charged with a number of firearms offences. He turned himself into police and was held for a bail hearing. The Crown was opposed to his release. His sister, Jameilah Darling, along with Bezia Wright, came forward to offer themselves as sureties. Jameilah Darling’s testimony at the bail hearing painted herself as a strong woman who would strictly enforce and supervise the terms of any release and not hesitate to contact police if she became aware he was breaching any of the release terms. The Justice of the Peace was convinced, in great measure by the strength of the release plan and the apparent preparedness and commitment of the sureties to supervise Juqjuan Darling, that he could be released. The terms of his release were very strict and included that he reside with Jameilah Darling, remain in his residence at all times each and every night unless he was in the company of one of his sureties or for medical emergencies or while meeting with counsel, not be in the front seat of any motor vehicle, and be subject to GPS monitoring. It is hard to envision any tighter bail conditions short of being detained in custody. Jameilah Darling was not, however, the strong surety she claimed to be. Not only did she fail to supervise and enforce the terms of her brother’s release, when she was made aware that her brother had fled from police who were trying to arrest him, she assisted him to escape by providing him with scissors to cut off his GPS ankle monitor, and then provided him with information from one of his associates about what they were trying to do to assist him to make good his escape and where he should flee to. Ms. Darling was not just a passive or lax surety, but someone who actively assisted her brother to escape and for that she was charged with obstructing justice, pled guilty, and is now to be sentenced.

[2] While there was agreement that Ms. Darling provided Juqjuan Darling with the scissors to cut the ankle bracelet off, the Crown and defence did not agree about other, admittedly aggravating, facts and so a Gardiner Hearing 1982 CanLII 30 (SCC), [1982] S.C.J. No. 71 was held in which the Crown was required to establish aggravating facts beyond a reasonable doubt. As my Ruling (released January 5, 2026) set out, the evidence established that Ms. Darling’s act of handing her brother scissors on April 16, 2024 was simply the culmination of her failure to supervise Juqjuan Darling’s conduct in the community that escalated from her turning a blind eye to his breaches of his bail, to her actively and wilfully abetting them.

[3] The Crown and defence are far apart in what they say is the appropriate sentence for Ms. Darling’s conduct. The Crown submits that Jameilah Darling actions as a surety strikes at the heart of the bail process and requires a 2 year less a day sentence of imprisonment. The defence submits that for a first offender such as Ms. Darling, with the background that she has had and her positive prospects for rehabilitation, that a 3-6 month conditional sentence is appropriate. Not surprisingly, given the uniqueness of the circumstances, neither counsel has been able to locate a case where a surety has actively assisted an accused to escape. The Crown analogizes the circumstances in this case to cases where individuals have intimidated witnesses to subvert the justice system whereas the defence likens this more to typical obstruct justice cases.

The Bail Hearing

[4] On June 19, 2022, Juqjuan Darling was alleged to have left a fully loaded overcapacity modified Glock firearm, with its serial numbers defaced, in the washroom of a downtown restaurant, and found himself facing 21 criminal charges, including 18 firearms related offences, two counts of failing to comply with release order and one charge of fail to comply with probation. At the time, he was already on an undertaking with conditions for dangerous operation and failing to comply with probation from July 29, 2021 and dangerous driving, failing to stop and two counts of failing to comply with a release order from August 15, 2021.

[5] Juqjuan Darling’s criminal record included convictions in 2015 for possession of a loaded prohibited or restricted firearm, breaching a weapons prohibition order, possession for the purpose of trafficking and breach of recognizance that netted him a 4 year sentence, then a breach of recognizance conviction in 2018.

[6] I point this out not to hold Jameilah Darling responsible for her brother’s criminal history, but to highlight the seriousness of the offences he was facing, his history of breaching court orders, the then current similar allegations, and the appreciation that any surety would have of the need for strong supervision if he was released, and the potential danger to the community if that supervision was lacking.

[7] At Juqjuan Darling’s bail hearing on August 2, 2022, it was proposed that he could be released with conditions that would require him to reside with his sister, only be out of the residence if he was in the company of one of his sureties, and be subject to GPS monitoring. Ms. Darling supported that in her testimony at the bail hearing. She described herself and Ms. Wright as strong women who would not let the accused push them around. She told the court that if Juqjuan Darling is under her supervision, she would check his belongings on an ongoing basis, monitor his friends to make sure no one supplied him with anything that she might deem inappropriate, and gave the impression that she was committed to ensuring that he was never left alone. If she had to drop her daughter off for school or go shopping, rather than leave him alone in the house, she testified that she would have him come with her and described not even going to a mall or store without him. She insisted that as he would be required to wear a GPS ankle monitor, that she would call Recovery Science Corporation any time they left their residence.

[8] Ms. Darling clearly understood that if her brother breached his bail, the money that she was pledging, which represented all of her savings, would be lost. She testified that that she was confident that as family she could be more controlling of him and be “on him everyday to make sure he is doing what he is supposed to do” and follow her rules. She testified that she saw her role as not just being his surety, but to help “keep him on track to do well in his life”. If she found out he was breaching any rules of the bail, she made it clear that she would be prepared to pull the bail even though it would mean putting her brother back in jail.

[9] The Justice of the Peace found the release plan to be a strong one. It led him to conclude that Juqjuan Darling had shown cause why his detention was not justified on the secondary ground, and that the strong release plan proposed “makes it highly unlikely for the defendant to re-offend.”

[10] Mr. Darling was released on a strict bail requiring him to reside with Jameilah Darling at her residence, unit 104-3023 Parkerhill Road in Mississauga, and remain in his residence at all times each and every night unless he was in the presence of one of his sureties or for medical emergencies or while meeting with counsel. He was also required to wear a GPS ankle monitor. On February 28, 2023, Juqjuan Darling’s bail was varied as he and Jameilah Darling were moving to a new residence, unit 244-1145 Journeyman Lane in Mississauga, as of March 1, 2023.

[11] At the Gardiner Hearing, it was established that on April 15, 2024, Juqjuan Darling had attended JP Bar and Grill and, as he admitted in a subsequent telephone call he had with an unknown female that was captured by police, assaulted a female acquaintance there. He then left the bar just before midnight and travelled to Hamilton where he remained until 5:01 p.m. on April 16th. His bail required him to reside with Jameilah Darling each and every night at 1145 Journeyman Lane. He was clearly not abiding by the terms of his release, and contrary to what Ms. Darling told the Justice of the Peace at his bail hearing to procure her brother’s release from custody, she did not contact police.

[12] On April 17, 2024, following a number of bail compliance checks, police made the decision to arrest Juqjuan Darling for breaching his bail. That evening, after police watched him leave 1145 Journeyman Lane and get into the driver’s seat of a vehicle that was parked outside his residence and drive away, which violated the term of his bail that he not be in the driver’s seat of any motor vehicle, they attempted to stop and arrest him. Juqjuan Darling managed to evade the police and fled.

[13] At 8:34 p.m., Juqjuan Darling called Jameilah Darling to let her know that the police were trying to arrest him and he needed to cut off his GPS ankle monitor. When he asked if she had scissors, she told him she did. Despite Ms. Darling having indicated in support of the bail variation that they were moving from 3023 Parkerhill Road to 1145 Journeyman Lane, significantly, Juqjuan Darling did not drive to 1145 Journeyman Lane but to 3023 Parkerhill Road as that was where Jameilah Darling was. At 8:37 p.m., he called her back to tell her he was on his way. Ms. Darling thought that the police were seeking to arrest her brother for the assault the night before at JP Bar and Grill. Her response provides a window into her view of the police and the criminal justice system. She expressed no empathy for the victim and no concern that her brother was committing criminal offences while on bail that she was responsible for supervising. Instead, she referred to the victim and the victim’s decision to contact police in derogatory terms, stating “Damn, bitch called the police and ratted”, before asking her brother what kind of scissors he needed and whether he needed big scissors. At 8:41 p.m., Juqjuan Darling pulled up to the front door, and Jameilah Darling ran out and handed her brother the scissors. Within one minute, he had cut off his ankle monitor and discarded it on the street.

[14] As I found, it was clear from the police surveillance and GPS monitoring data, that Juqjuan Darling’s residence was, at least after March 1, 2023, 1145 Journeyman Lane. There was a constellation of other evidence that strongly suggested that Ms. Darling was still residing at 3023 Parkerhill Road and had not moved to Journeyman Lane with her brother. The evidence, in its entirety, established beyond a reasonable doubt that Juqjuan Darling was not residing with Jameilah Darling and that she was continuing to reside, at times, at 3023 Parkerhill Road notwithstanding the bail variation and bail term required Juqjuan Darling to reside with her at 1145 Journeyman Lane each and every night.

[15] While Ms. Darling tried to explain her actions as being in “panic mode”, providing her brother with scissors to cut off his ankle monitor was not a single, panicked reaction, but the last of her acts that demonstrated her disregard of her obligations as his surety which culminating in her facilitating his escape, not just from police but from the province. Police intercepted a telephone call between Ms. Darling and her brother at 8:50 p.m., after he had cut off the ankle monitor, in which she tells him that she was just talking to “Richie” and they are telling him they are trying to get him out of that car and he needs to get out of here and go to “the Peg” or something like that. Those were not the words of someone who was remorseful of what she had done, but of someone who was fully committed to assisting her brother to evade the police.

[16] Jameilah Darling was well aware that her brother was not abiding by the terms of his bail and had engaged in criminal conduct; an assault at a bar and flight from police. Her words and actions demonstrated that her allegiance to her brother overwhelmed her obligation to the court and the community. The risk her brother posed to the public after being charged with firearm offences was only manageable because of the proposed sureties’ sworn preparedness to vigilantly supervise him. Ms. Darling convinced the court to release him because of her strength as a surety, but once he was released, she was delinquent in her supervision and facilitated his escape from police and flight from the jurisdiction.

The offender

[17] An Enhanced Pre-Sentence report was prepared which provided insight into Ms. Darling’s life circumstances. The report provided a fulsome picture of Ms. Darling’s life as a Black woman of Jamaican descent who grew up in what are euphemistically described as challenged neighbourhoods in Toronto with her mother and three brothers.

[18] Jameilah Darling is now 32 years old and a single mother of an 11 year old daughter. Growing up, her family had financial challenges, lived in a shelter for some time, and then were offered subsidized housing in Rexdale. Their neighbourhood was primarily black with racialized families experiencing similar financial hardship to her own family. It was also a neighbourhood that was characterized by gun violence and drug dealing.

[19] Ms. Darling reported that the neighbourhood was welcoming; however, the high crime rate and risk that existed in the community contributed to poor living conditions. Jameilah Darling, along with her three brothers, were raised in a home by her mother who experienced the hardships of single parenthood and poverty. Ms. Darling did not know her father for most of her life and first spoke to him when she was 12 or 13 years old. Her childhood was described as unstable, unstructured, and lacked oversight. Her older brothers were involved in gang-related criminality and “in and out of jail a lot”. Her younger brother, Juqjuan “was always into trouble at school” and often suspended. Ms. Darling reported that as a result of her brothers’ conduct, she was afraid to go to school because she was concerned about retaliation against her family.

[20] Ms. Darling observed a “strong police presence” in Rexdale and saw them “almost every day” in the neighbourhood. She was acutely aware of the police due to their frequent visits to her home and observed “a lot of police officers” beat up one of her brothers and continue despite her screaming at them to stop. She described the experience as “scary” and caused her to be fearful of the police. She reported that the police contacts with other Black men in the neighbourhood were largely negative and resembled harassment when they stopped them and asked numerous questions. While expressing that there are “good and bad [police] out there, she believed that the police like to “stir up trouble” and characterize Black men as “up to no good” because of their racial identity, how they dress and the neighbourhoods they live in and that Black women were seen as being “just as bad as Black men…and do stuff for them”.

[21] As a result of a police raid on their home, Ms. Darling and her family moved to Malton in 2009, but the living circumstances apparently did not change except that they were no longer living in community housing. Growing up, Ms. Darling would visit her grandmother’s home in Scarborough where the “environment was different” and gave her a break from her unstable home life. Ms. Darling’s mother confirmed that she spent most of her time with her mother given the attention her sons required of her.

[22] Jameilah Darling reported that she struggled at school and attended until grade 11 before enrolling in an adult school. She began working on an off and attending college in the medical office administration program in September 2015 and had completed 70% of the program when her brother was murdered and her child’s father was hospitalized. She did not finish that program but later completed a nail technician course. She advised that she has sought employment since her conviction but has been unsuccessful as many jobs require a criminal records check so she has chosen not to pursue employment until her sentencing is completed and feels that working independently may be her best option.

[23] In the absence of her father, Ms. Darling was particularly close with her oldest brother, Jamahl, as he was protective and the “one [she] could talk to”. When Ms. Darling was 21, Jamahl was murdered. She has recently begun to receive counselling to process and understand her feelings with respect to this loss. Jameilah is not close to her second oldest brother, Jermaine, who has been incarcerated since 2008 and is serving a life sentence. Juqjuan Darling is one year younger than Ms. Darling. She reported that they were close growing up and she considered him to be the “protector”. She described having a close relationship with Juqjuan and him being “very supportive” and “helpful” towards her and her daughter including providing respite, being present, and offering financial support. It was for these reasons that she felt “obligated” to Juqjuan and agreed to be his surety as a way to “give back”.

[24] The father of Ms. Darling’s daughter has minimal involvement in their lives due to his infidelity and criminal lifestyle. Ms. Darling described her relationship with her daughter as one that doesn’t resemble the one she had with her own mother, and she has strived to provide her daughter with a stable life.

[25] Ms. Darling is described as a “great mother” by those around her. If a custodial sentence is imposed, her mother will care for her daughter. Britany Taylor, a close friend, noted that if her friend was separated from her daughter, it would be one of the “hardest, heartbreaking times”, but she too would be prepared to care for Ms. Darling’s daughter if needed.

[26] Ms. Darling expressed concern about the sentencing process and its implications for her and her daughter’s future. She felt, naturally, that being away from her daughter, even for a short period, would be detrimental, but confirmed that her mother and best friend would take care of her daughter if a custodial sentence was imposed.

[27] Ms. Darling expressed that she was very disappointed in herself for getting in trouble with the law. She described to the EPSR author that she agreed to be a surety for her brother but did not know how difficult being a surety would be until she became one for Juqjuan. She said that it was “stressful” and difficult to supervise Juqjuan when it came to going out because he “is an outside person and [she is] not”.

[28] Jameilah said that she complied with Juqjuan’s request for scissors to cut his ankle monitor off because he was “panicking” and she was also in “panic mode”. She claimed that she did not consider the consequences of her actions in the moment but recognized, after the fact, that “[she] should not have done that”. She explained that “sometimes it is hard to tell Juqjuan no” and being “just so used to doing what he asks”, she complied with her brother’s request. She described herself as a “people pleaser” and has struggled in the past to decline the requests of others because she does not want to let people down. She claimed that she did not want Juqjuan to be “angry”, as being the recipient of his outbursts “can be kind of scary”. She denied feeling threatened by Juqjuan, but wanted to avoid being on “his bad side” if she said no.

[29] She recognized that her decision to help her brother was “dumb” and “irresponsible” and regretted her choices “with everything [she has] and if [she] could go back in time [she] would”. She vowed never to make a mistake like this again, that it does not define who she is, and is deeply apologetic for her missteps.

[30] For the past three years, Ms. Darling has been working with a counselling organization, Think 2wice, to assist with her grief around her brother, Jamahl’s, death. She has also participated in group training activities and speaking engagements to talk about her personal story. Her counsellor described Ms. Darling as an intelligent, talented young woman and “a gem” in their groups, and that telling her personal story “resonated with others”. Aftercare services have been offered to Ms. Darling following her sentence.

[31] It was the EPSR author’s opinion that Ms. Darling has taken the time to reflect on her actions and has gained insight into their severity, and acknowledged that despite her effort to assist her brother, her actions were not only detrimental to him, but also to herself. It was her view that the relationship between Jameilah and her brothers is central to her story.

[32] The author noted the growing overincarceration of Black women. They make up 3% of the adult general population in Canada but represent 9.12% of federal inmates in women's institutions. The report noted how separation resulting from incarceration has detrimental effects on children and families and threatens children’s emotional, physical and financial well-being. The author observed how the separation of mother and daughter if Ms. Darling was incarcerated is particularly salient and relevant to her circumstances and that despite the circle of support she has in her mother and best friend who are prepared to assist if she receives a jail sentence, the impact of any separation would be largely negative due to the close relationship and bond Ms. Darling and her daughter share.

[33] Ms. Darling expressed a commitment to improving herself and has connections to community support who can assist her with rehabilitation. She is remorseful for her decisions and has vowed never to be involved with the criminal justice system again. Collateral sources were confident that Ms. Darling can create a positive and bright future for herself and her daughter post-sentencing.

Crown position

[34] The Crown analogizes Ms. Darling’s conduct with the line of cases dealing with intimidation of witnesses as both strike at the heart of the criminal justice system and both call principally for the imposition of a denunciatory and deterrent sentence. The Crown submits that a surety assisting an accused to cut off his ankle monitor to flee the police and the jurisdiction, is as serious an obstruction of justice as one can commit.

[35] The Crown disputes Ms. Darling’s attempt to excuse her conduct by claiming to have been overwhelmed by “panic” and submits that it minimizes her acceptance of responsibility and that how she portrays herself now is at odds with how she portrayed herself at Juqjuan Darling’s bail hearing. There, she expressed with confidence her ability to oversee and influence and govern her brother’s behaviour especially because they would essentially always be together. Now, when having to face responsibility for her lack of oversight and conduct, claims that she did not have influence over him nor could she ensure that they were always together. She was also not prepared to contact police as she claimed convincingly, although falsely, to the Justice of the Peace.

[36] The Crown asserts that she did not provide scissors to her brother so that he could cut off his ankle monitor out of panic, but because it was a continuation of her decisions not to enforce his bail terms and allow him to live as he wished despite his criminal record for firearms and violence.

[37] The Crown characterized Ms. Darling’s conduct as a significant dereliction of her duty as a surety. If the public was to have any confidence in the bail system it relies on the duty of members of the public to take their role as sureties seriously. Members of the public would be appalled at her conduct. It undermines public confidence in the bail system which underlines the seriousness of the obstruction. Her claimed commitment to vigilantly supervise her brother in the community and ensure he did not breach any of the terms of a release order was relied upon by the Justice of the Peace to release him, but once released, Ms. Darling failed to do what she said she would, and was obliged to do as his surety, and then further breached the court’s trust by actively assisting him to violate the terms of his release and flee from the jurisdiction.

[38] Ms. Darling would have been well aware of the danger Juqjuan Darling presented to the community from his criminal record, and also from the facts read into the record, and yet she allowed him to have essentially free rein with minimal supervision. She turned a blind eye to his breaches of bail, facilitated his flight from police, and then acted as a messenger to give her brother advise from a presumed criminal associate about changing vehicles and where he should flee to.

[39] In the Crown’s view, it is hard to imagine a worse obstruction of justice by a surety, and, in the context of bail, it is the worst offence. A properly informed member of the public who thought a surety could do what Ms. Darling did and walk away with the minimal consequences that a conditional sentence would bring, would be appalled, and that only a real sentence of imprisonment is appropriate and consistent with the principles of sentencing.

[40] The overall goal of the criminal law in general, and the law of bail, is, as noted in Trotter, The Law of Bail in Canada, 3rd Ed., Chapter 1:31 ..“[t]he protection of society. The protection of the public is a concern that cannot be ignored in any rational discussion of bail. In a way, most of the normative principles attempt to qualify the unbridled pursuit of this goal. They direct how the goal may be achieved while maintaining public acceptability.” As the Crown argues, if the responsibilities of a surety are not enforced, how can the public have confidence in the bail system?

[41] In R. v. Jones 2021 ONSC 2322 at para 27-28, Justice Goldstein described the importance of the surety within our bail system as follows:

The purpose of the surety system is to use a trustworthy individual to act as the eyes and ears of the court; or to put it less delicately, act as a substitute jailer: R. v. Seymour, [2004] O.J. No. 5834 at para. 60; United States of America v. Shahid, [2020] O.J. No. 4585, 2020 ONSC 6308 at para. 44.

Typically, justices of the peace or judges assess the suitability and reliability of a potential surety through viva voce evidence. All sureties always pledge that they will supervise the accused; call the police if the accused does not follow the rules; and ensure compliance with the terms of the recognizance. Of course, the reality is that some sureties are unable or unwilling to actually perform those duties. Justices of the peace or judges must determine whether the surety really will enforce the rules. Since sureties are often close family members, justices of the peace or judges must also determine whether sureties really will call the police or pull their suretyship in the event of a breach. No surety is perfect, and no plan is perfect, of course, and a court cannot expect a standard of perfection. It is a question of risk management: will the surety reduce the risk of the accused committing further offences such that the court is satisfied that there is no substantial likelihood that he or she will?

[42] The Crown referred to R. v. Hopwood 2020 ONCA 608 at para 22-24, to support its position that where the actions by the accused strike at the heart of the justice system akin to seeking to interfere with witnesses, the sentence imposed must firmly express society’s condemnation:

I begin with the principle that efforts by accused persons (whether directly or through others) to interfere with witnesses strike at the very heart of our justice system. There are already very serious concerns regarding the willingness of people, who observe crimes, to come forward and offer themselves as witnesses. Concerns around the "code of silence", and possible repercussions from being considered a "rat" or a "snitch", often lead persons to remain silent when they ought to be coming forward and assisting the authorities to properly investigate and prosecute criminal activities.

Against that backdrop, interference with persons who are prepared to be witnesses only serves to exacerbate the problem. It must be clear to all accused persons that attempting to interfere in any way with a witness represents conduct that will not be tolerated. In that regard, I respectfully adopt what the British Columbia Court of Appeal said in R. v. Hall, [2001] B.C.J. No. 560, 2001 BCCA 74, per Saunders J.A., at para. 12:

Obstruction of justice or attempting to obstruct justice strikes at our system of a lawful society. The message must be clear that this type of interference with the community system for handling criminal offences will not be tolerated. It is for this reason that the courts must act firmly to express society's disapproval and denunciation of such conduct.

While there may be other conduct that would constitute an attempt to obstruct justice that would warrant a minor sentence of the type that was imposed here, attempting to interfere with a witness does not fall into that category. Indeed, I would say that, as a general proposition, attempting to interfere with a witness should normally attract a penitentiary term of imprisonment.

[43] The Crown provided a number of sentencing decisions where the accused had either attempted to or had obstructed justice by interfering with a witness. In cases in which an accused attempted to have a co-accused change his testimony to exonerate the accused, a 2 ½ year sentence has resulted (R. v. Hopwood 2020 ONCA 608, R. v. Williams 2016 ONCA 937). In R. v. McGregor [2025] O.J. No. 5790 (C.J.), the accused, the victim of an attempt murder, accepted a bribe to create a false police statement that recanted his earlier statements. He had a lengthy criminal record and received an 18 month term of imprisonment.

[44] In R. v. Mussie 2024 ONSC 4807, the accused arranged for a woman to forge an employment letter in return for fentanyl which he then provided to support a bail application. He had no criminal record and received a 1 year sentence for obstruct justice concurrent to a 6 year sentence for human trafficking offences.

[45] In R. v. Dubros 2023 ONCA 447, the accused private detective with no criminal record had been hired by defence counsel to "dig up dirt" on the complainant and witnesses in an Intimate Partner Violence case. He attempted to intimidate or threaten the complainant to resolve the charges for a peace bond. The accused was 62 years old and suffered from a myriad of mental health disorders which may have contributed to the commission of the offence. The trial judge imposed an 18-month sentence. On appeal, the Court found that the sentencing judge overemphasized deterrence which led to a "disproportionate and manifestly unfit" sentence. The court found fresh evidence confirming the loss of his licence to be a relevant collateral consequence that meant that the Appellant would not be in a position to commit the offence again, and described the circumstances as unique in that the appellant did not have any personal interest in the outcome of the case in substituting a two-year less one day conditional sentence.

[46] R. v. Jackson 2022 ONCJ 430, was a case in which the judge imposed the 90 day conditional sentence that the Crown was seeking for an offender who made plans to physically prevent an alleged victim from testifying and offered to assist in hiding a firearm used during the offence. But for the Covid-19 pandemic, the Crown would have sought a sentence of incarceration. The sentencing judge observed that:

12 Conduct that would subvert the justice system and purport to interfere with the ability of witnesses to testify is gravely serious. Even in cases where an offender is otherwise a law-abiding citizen with no criminal background, courts must treat such conduct severely. A sentencing court cannot ignore the positive antecedents of a particular offender, but the gravity of the offence is such that denunciation and deterrence must be given paramount consideration.

14 In the present case, the Offender made plans to physically prevent an alleged victim from testifying, and she offered assistance in hiding important evidence. Her conduct is of the utmost seriousness.

Defence position

[47] The defence also relied on Jackson in support of the imposition of a conditional sentence in Ms. Darling’s case. R. v. Schmidt 2019 ONSC 3939 was case in which the offender was a farmer being investigated for producing raw unpasteurized milk for sale. When an Inspector sought to leave with property seized after executing a search warrant, Mr. Schmidt told supporters who were at the farm to prevent them from leaving and to get arrested if needed. A 30 day conditional sentence was ultimately imposed following a Summary Conviction Appeal.

[48] In R. v. Schertzer [2015] ONCA 259, officers with the Toronto Police Drug Unit were found guilty of attempt to obstruct justice and perjury for altering notes and testifying falsely about conducting a search before obtaining a search warrant. The trial judge imposed 45 day conditional sentences, which the Court of Appeal found was demonstrably unfit and failed to denounce the offending officers’ conduct, and would have imposed 3 year sentences but stayed the sentences given the passage of time since the offence.

[49] R. v. Petrolo [2020] ONCJ 122 involved a prosecutor offering favourable dispositions for friends of her then boyfriend on two occasions. The accused did not do so for financial gain but simply as a favour. As a result of her arrest, she was fired, had restrictions placed on her employment as a paralegal and faced extensive media coverage. The Crown sought a 9 month conditional sentence while the defence sought a conditional discharge. Much of the judgment focuses on the appropriateness of a discharge, but the sentencing judge ended up imposing a 3 month conditional sentence.

[50] In R. v. White 2016 ONSC 4654, a 6 month custodial sentence was imposed for obstruct justice concurrent to the same sentence for trafficking in cocaine. The obstruct justice charge was for Mr. White putting drugs into his mouth when he realized he was being arrested before spitting them out so that the drugs could be seized from him.

Analysis

[51] In R. v. Parranto 2021 SCC 46, 2021 S.C.J. 46, the Court wrote:

9 This Court has repeatedly expressed that sentencing is "one of the most delicate stages of the criminal justice process in Canada" (R. v. Lacasse, 2015 SCC 64, [2015] 3 S.C.R. 1089, at para. 1). More of an art than a science, sentencing requires judges to consider and balance a multiplicity of factors. While the sentencing process is governed by the clearly defined objectives and principles in Part XXIII of the Criminal Code, it remains a discretionary exercise for sentencing courts in balancing all relevant factors to meet the basic objectives of sentencing (Lacasse, at para. 1).

10 The goal in every case is a fair, fit and principled sanction. Proportionality is the organizing principle in reaching this goal. Unlike other principles of sentencing set out in the Criminal Code, proportionality stands alone following the heading "Fundamental principle" (s. 718.1). Accordingly, "[a]ll sentencing starts with the principle that sentences must be proportionate to the gravity of the offence and the degree of responsibility of the offender" (R. v. Friesen, 2020 SCC 9, at para. 30). The principles of parity and individualization, while important, are secondary principles.

[52] The fundamental purpose of sentencing set out in s.718 of the Criminal Code provides that the sentence imposed by the court should have one or more of the following objectives:

(a) to denounce unlawful conduct and the harm done to victims or to the community that is caused by unlawful conduct;

(b) to deter the offender and other persons from committing offences;

(c) to separate offenders from society, where necessary;

(d) to assist in rehabilitating offenders;

(e) to provide reparations for harm done to victims or to the community; and

(f) to promote a sense of responsibility in offenders, and acknowledgment of the harm done to victims or to the community

[53] Section 718.2 identifies additional principles of sentencing including: (b) [that] a sentence should be similar to sentences imposed on similar offenders for similar offences committed in similar circumstances, which given the unique circumstances of Ms. Darling’s offence, has required comparisons by analogy, and particularly the principles of restraint which requires that (d) an offender should not be deprived of liberty, if less restrictive sanctions may be appropriate in the circumstances, and (e) all available sanctions, other than imprisonment, that are reasonable in the circumstances and consistent with the harm done to victims or to the community should be considered for all offenders. Put another way, what is the least restrictive sentence capable of meeting the various sentencing principles at play?

[54] The determination of a just and appropriate sentence is a highly individualized exercise that goes beyond a purely mathematical calculation. (Lacasse, para 58) In Ms. Darling’s case, her personal circumstances provide a window into why this otherwise law-abiding, single mother chose to align herself with her brother over her obligations to the court. Jameilah Darling’s conduct as Juqjuan Darling’s surety would have sent Mr. Darling the very clear message that not only would she not be enforcing the release order he was subject to, but she would not be contacting the police. It is not hard to understand why Juqjuan Darling contacted his sister to provide him with scissors to cut off his ankle monitor because, from her past actions, or inactions, as his surety, he would have been confident that not only would she provide him with the tools to escape but would not be reporting him, nor his potential whereabouts, to the police. Why she would do that goes back to the comment made by the author of the Enhanced PSR: “The relationship between Jameilah and her brothers are…central to her story.”

[55] Juqjuan Darling was, to Ms. Darling, her only brother left. Her family were mired in the criminal justice system: A brother murdered, another brother serving a life sentence, and the third clearly engaged in criminality that she supported. The potential impact of Ms. Darling’s experiences with criminality and policing within her own family and the response of the justice system is both relevant to understanding her own involvement in the criminal justice system, and determining a fit sentence

[56] Ms. Darling’s personal circumstances must, however, be balanced or gauged against the seriousness of the offence. Denunciation and deterrence are the most important sentencing objectives but must be tempered by the positive prospects for rehabilitation and the principle of restraint.

[57] In the case of a first offender, the primary objectives in sentencing are individual deterrence and rehabilitation. Before imposing a custodial sentence, the sentencing court should explore other dispositions that are available and only impose a custodial sentence where the circumstances are such, or the offence is of such gravity, that no other sentence is appropriate. (R. v. Priest 1996 CanLII 1381 (ON CA), [1996] O.J. No. 3369 (C.A.) at para 17 referring to R. v. Stein (1974), 1974 CanLII 1615 (ON CA), 15 C.C.C. (2d) 376 (Ont. C.A.) at page 377)). If a first sentence of imprisonment is to be imposed, it should be as short as possible and tailored to the individual circumstances of the accused rather than solely for the purpose of general deterrence. (Priest, para 23)

[58] The more serious the offence, however, the stronger the need to denounce the unlawful conduct and deter the offender and others from further offending. (R. v. Morris 2021 ONCA 680 at para 69). As the Court noted in Morris:

When the gravity of the offence demands an emphasis on denunciation and deterrence, the proportionality principle will most often require a disposition that includes imprisonment. Wagner J. (as he then was) observed in Lacasse, at para 6:

[A]s in all cases in which general or specific deterrence and denunciation must be emphasized, the courts have very few options other than imprisonment for meeting these objectives, which are essential to the maintenance of a just, peaceful and law-abiding society. (Morris, para 70)

[59] It is hard to gauge exactly the impact of overt and systemic racism Ms. Darling may have experienced and its impact on her decision to engage in the criminal conduct in issue here, but her experiences as a young girl and then a woman within the challenged neighbourhoods she resided in would appear to have a connection to the choices she made. Those experiences impact Ms. Darling’s moral culpability because they did impact her choices and so become relevant in determining the appropriate sentence to be imposed.

[60] Ms. Darling’s experiences were of her own family and those within her community being targeted by police. Her own family’s contact with police is qualified by the fact that her brothers were involved in gang activity, in and out of the criminal justice system with one becoming a victim of crime, another a perpetrator serving a life sentence, and the third, Juqjuan, clearly involved in criminal activity that then involved Ms. Darling. Her perception of her community and her relationship with the police and criminal justice system played a role in shaping her decision-making. When called upon to choose between her allegiance to the court by properly supervising her “remaining” brother’s release and her allegiance to that brother, she chose the latter.

[61] It must be stressed, however, that Ms. Darling’s view of the criminal justice system and the role she assumed, however impacted by her life experiences, is of limited mitigation. She still chose to enable Mr. Darling to do as he wished, and by not supervising him and ensuring he complied with the release order, put members of the public at risk.

[62] I appreciate that, as the Court in Morris said, “the use of conditional sentences when sentencing young Black offenders, in appropriate cases, also carries the added advantage of addressing, at least as it relates to the offender before the court, the ongoing systemic problem of the over-incarceration of young Black offenders.” (Morris, para 129). I also recognize the significant collateral consequences of the impact incarceration will have on Ms. Darling and her daughter although attenuated to some degree by Ms. Darling’s own mother and best friend being prepared to assist.

[63] As set out in R. v. D.B. 2025 ONCA 577 at para 12, “collateral consequences humanize and individualize sentencing by accounting for its effects other than the criminal sanction itself. The Court restated the principles governing collateral consequences from R. v. Pham 2013 SCC 15 and recognized that when families are disrupted it “make[s] the rehabilitative path harder to travel, hinders "future reintegration, and can reduce the need for denunciation and deterrence.”

[64] Although denunciation and deterrence are paramount given the offence’s seriousness, proportionality requires considering the collateral consequence of the family separation which increases the sentence’s impact. (See D.B., para 25). Ms. Darling’s guilty plea, lack of a criminal record, and community and family supports suggest strong rehabilitative potential that warrant moderating the sentence.

[65] As both Crown and defence agree, it is fitting that a custodial sentence be imposed. What is to be determined is whether that custodial sentence be served in the community by way of a conditional sentence. In considering whether, in the circumstances of this case, a conditional sentence is a fit and proportionate sentence in light of all of the aggravating and mitigating circumstances, it is worth going back to Chief Justice Lamer’s words in R. v. Proulx 2000 SCC 5, [2000] 1 S.C.R. 61:

100A conditional sentence can achieve both punitive and restorative objectives. To the extent that both punitive and restorative objectives can be achieved in a given case, a conditional sentence is likely a better sanction than incarceration. Where the need for punishment is particularly pressing, and there is little opportunity to achieve any restorative objectives, incarceration will likely be the more attractive sanction. However, even where restorative objectives cannot be readily satisfied, a conditional sentence will be preferable to incarceration in cases where a conditional sentence can achieve the objectives of denunciation and deterrence as effectively as incarceration. This follows from the principle of restraint in s. 718.2(d) and (e), which militates in favour of alternatives to incarceration where appropriate in the circumstances.

102…Incarceration will usually provide more denunciation than a conditional sentence, as a conditional sentence is generally a more lenient sentence than a jail term of equivalent duration. That said, a conditional sentence can still provide a significant amount of denunciation. This is particularly so when onerous conditions are imposed and the duration of the conditional sentence is extended beyond the duration of the jail sentence that would ordinarily have been imposed in the circumstances…

106The amount of denunciation provided by a conditional sentence will be heavily dependent on the circumstances of the offender, the nature of the conditions imposed, and the community in which the sentence is to be served. As a general matter, the more serious the offence and the greater the need for denunciation, the longer and more onerous the conditional sentence should be. However, there may be certain circumstances in which the need for denunciation is so pressing that incarceration will be the only suitable way in which to express society's condemnation of the offender's conduct.

[66] While I recognize some distinction in supervising a court order as opposed to being subject to one, it is not lost that Ms. Darling facilitated and abetted non-compliance with a court ordered release in the community that she submits she will comply with if subject to herself in the community. I have considered whether a sanction other than imprisonment would be reasonable and appropriate in this case and it is my view, notwithstanding Ms. Darling’s lack of a criminal record and her personal circumstances, that there is not. Even if I was confident that Ms. Darling would abide by the terms of a court ordered sentence to be served within the community, having that sentence served in the community would not, in my view, effectively denounce nor deter the kind of conduct she engaged in. As surety, she exhibited a blatant disregard for her obligations to the court and took active steps to assist the accused, her brother, to violate those terms and escape from the police and the jurisdiction. Her conduct demonstrated little or no regard for the court’s ordered terms. She was not prepared to require to have her brother comply with them and engaged in acts to subvert the bail process, whether by ignoring what she was required to do as a surety, or acting to assist his escape so that he could conceal his whereabouts and flee from police.

[67] Ms. Darling’s conduct was so serious that the need for denunciation is so pressing that incarceration is the only suitable way to express society’s condemnation of her conduct. She was a surety who was not only indifferent to the bail terms she was supposed to be supervising and enforcing, she failed to contact police when she became aware of Juqjuan Darling’s breaches of his bail, failed to contact police when aware that he was alleged to have assaulted someone, and when asked to assist him to cut off his GPS ankle monitor so that he could escape from the police and jurisdiction, willingly did so. That act was not a single panic-driven offence, but one that was entirely in keeping with her disregard of his court order. I recognize the impact in separation Ms. Darling, a first offender, from her daughter, but in my view, nothing less than a real term of imprisonment would appropriately denounce and deter her criminal conduct which did indeed strike at the heart of the bail and justice system.

[68] Considering all of the mitigating and aggravating circumstances, including the collateral impact of such a sentence on her family, I am of the view that a sentence of 12 months imprisonment is the fit and appropriate sentence in this case. Ms. Darling is already engaged in counselling and committed to a path of rehabilitation and so a probation order is not necessary. The victim fine surcharge will be waived given the obvious financial hardship it would cause.

Released: August 4, 2026