ONTARIO COURT OF JUSTICE

DATE: 2025-07-04
COURT FILE No.: 23-48114637; 23-48118605; 23-48119247; 23-48125541; 24-48104346; 24-48108207; 24-48115184; 24-78700005; 21-75001820; 24-48125512; 24-48125514; 24-50000254
Toronto Region

B E T W E E N :

HIS MAJESTY THE KING
— AND —
DYLAN VICTOR McCORMACK-WOOLACOOT

Before Justice H. Pringle
Heard on May 29 and June 20, 2025
Reasons for Judgment released on July 4, 2025

Jean-Pierre D’Angelo ......................................................................... counsel for the Crown
Tony Paas ...................................................................................... counsel for the defendant

PRINGLE J.:

OVERVIEW OF CASE

[1] Mr. McCormack-Woolacoot globally pled guilty to ten separate charges on May 29, 2025. His decision to do so resolved multiple informations, instead of setting twelve separate trials on each information before the court.

[2] The crimes he admitted committing were, for the most part, low level offending: shoplifting and minor assaults. But he committed these crimes, consistently, over an eighteen-month period and while he was supposed to be obeying multiple court orders. Additionally, two offences he committed raise concern about Mr. McCormack-Woolacoot’s future potential for inexplicable, unprovoked violence.

[3] The parties’ positions reflect agreement that a global sentence of between fifteen and sixteen months is fit for all offences, properly expresses denunciation and deterrence, and reflects all aggravating and mitigating factors. In submissions, the parties’ respective positions differed by twenty-four days.

[4] But the parties disagree about presentence custody credit. The defence sought Summers credit of 1.5:1 for each day served thus far. The Crown opposed, relying on the trial decision of R. v. Jeyakanthan, 2024 ONSC 1665.

[5] Globally, I concluded, a fit sentence was 460 days. I imposed 1.5:1 credit for every day of pre-sentence custody used towards that sentence.[^1] Mr. McCormack-Woolacoot will be released, placed on probation, will provide a DNA sample and be subject to a weapons prohibition order.

OVERVIEW OF THE OFFENCES

[6] In September 2022, the defendant was placed on a fifteen-month conditional sentence order and twelve months of probation. In August 2023, with four months left on his conditional sentence order, he attended a shelter on Strachan Avenue. For reasons unknown, he threw potatoes at a shelter worker and upended a cup of coffee onto a nearby car.

[7] About one month later, the defendant was shoplifting at Shoppers Drug Mart. When confronted, he pushed a shopping cart at a store manager to effect escape. Three weeks later, he came back to the same Shoppers Drug Mart and stole three bottles of perfume.

[8] Ten days after that,[^2] the defendant was released on bail. More than two uneventful months passed, but then Mr. McCormack-Woolacoot went back to that same shelter on Strachan. He was on bail conditions to stay away from the shelter and from that worker he assaulted. He breached both conditions, confronting the worker, hurling misogynistic insults at her, and then threatening her life.

[9] Mr. McCormack-Woolacoot’s next crime was a random attack on a stranger on March 2, 2024. The victim did nothing to provoke or deserve it. He was walking his dog when the defendant approached him, kneed him in the groin, and then punched him in the chest and hip. This victim provided input which proved he still struggles with trauma from this attack.

[10] Mr. McCormack-Woolacoot was globally released on a BP release six days later.[^3] A little over three months later[^4], Mr. McCormack-Woolacoot was at a Metro grocery store with an unknown female. She got caught stealing. To prevent her arrest, the defendant stood in between the Loss Prevention Officer (LPO) and the female and assaulted the LPO, causing soft tissue injury to the victim’s neck.

[11] Two months later, the defendant went back to the exact same Metro. His prior victim, the LPO, was there. Unprovoked, Mr. McCormack-Woolacoot threw a beer can at him. When the victim tried to effect an arrest for this assault, Mr. McCormack-Woolacoot jabbed him with a metal vape pen. He did this multiple times, causing blood to pool out of the victim’s ear. The victim was hospitalized and may have suffered ear drum damage.

[12] All this offending took place while Mr. McCormack-Woolacoot was supposed to be obeying his conditional sentence order or the subsequent probation order, as well as bail orders.

[13] On October 8, 2024, the defendant was globally released on bail, which directed him to be amenable to working with “Sound Times”. One month and one week after release[^5] he was shoplifting at an LCBO when, to prevent arrest, he hit an LPO on the side of the face and smashed a bottle on the floor. Following this arrest, the defendant was detained in custody.

[14] The man who Mr. McCormack-Woolacoot randomly assaulted on the street submitted victim impact evidence. The assault profoundly affected him. He is scared to leave his house and feels insecure in his neighbourhood. His letter describes screaming for help while Mr. McCormack-Woolacoot rained blows on him. He thinks about leaving this community for good. He carries these thoughts every day, and explained that:

…the psychological and emotional injuries have been long-lasting. I live with the persistent fear that something similar could happen again. I struggle with trust, and I often relive the moment in ways that interfere with my concentration, rest, and interactions with others. I have altered many of my routines to avoid distress, but even those changes bring their own burdens and reminders of what happened.

[15] While no other victim submitted a statement, I had no hesitation finding they also suffered profound impact, particularly those victimized twice – especially the LPO who was stabbed. I have no doubt the defendant’s actions haunt them both still.

[16] The defendant has a criminal record, with six prior convictions on CPIC and one conviction on the acknowledged 2022 conditional sentence order. His record began in 2014 and ends in 2022. There was no gap between 2022 and the current convictions, since he admitted offending in the community during most of this time. But the CPIC record has with a six-year gap in offending between 2014 and 2021.

[17] Two of his prior convictions are concerning – a robbery from 2021 where 18 months jail was imposed, and a 2022 robbery conviction which attracted the 15-month conditional sentence order. Probation has been imposed twice.[^6]

[18] Mr. McCormack-Woolacoot advised he is indigenous but has little connection to that heritage. The disconnection from his indigenous heritage is one well-recognized impact from colonization. He described his mother as schizophrenic and his father as an alcoholic. Mr. McCormack-Woolacoot was made a Crown ward at age four and remained one until age twenty-one. He lived in various foster homes during this time.

[19] At some point, the defendant attended Humber College. He has worked in restaurants, summer camps, and with one of his brothers in a painting business. But for two years prior to his November 2024 arrest, Mr. McCormack-Woolacoot was largely living on the streets. He had developed an addiction to crystal meth.

[20] Those two years reflected a spree of unchecked criminal offending. During that time, the defendant showed little to no respect for court orders, which is significantly aggravating. Those court orders were imposed to control his risk of offending. He ignored them. Community supports, made available to the defendant upon release, were unable to stop his offending.

[21] Part of his offending behaviour while not justified, is explicable. Stealing feeds his addiction. What is unclear and deeply troublesome is why, when Mr. McCormack-Woolacoot does not get his way, he resorts to violence.

[22] Mr. D’Angelo correctly noted that the people Mr. McCormack-Woolacoot victimized fall into the category of innocents, going about their day-to-day business. A shelter worker, a store manager, a loss prevention officer, and a stranger on the street who still does not know why he was attacked. Except for the last victim, Mr. McCormack-Woolacoot lashed out at people who opposed him in some way.

[23] This is concerning. Mr. McCormack-Woolacoot seems to lack proper coping or cognitive skills to react to opposition with anything but anger and violence, and life is full of opposition. Thinking about Mr. McCormack-Woolacoot’s upbringing and life experience, he has a lot to feel angry about. But unless something meaningful changes, I fear Mr. McCormack-Woolacoot will seriously hurt someone and spend much of his life in jail.

[24] Mr. McCormack-Woolacoot represented himself at his last bail hearing, where we met. He presented as intelligent and articulate. He spoke compellingly about making safe use drug kits for other marginalized people. The evidence in the bail hearing led me to detain him. I could not help but observe a wealth of untapped potential in this man.

[25] I am hopeful that Mr. McCormack-Woolacoot’s probation officer will assist him in finding, and completing, culturally appropriate counseling which meaningfully addresses his substance use disorder, anger management, and childhood trauma.

OVERVIEW OF PRESENTENCE CREDIT

[26] The Crown sought a global sentence of 15.7 months, or 480 days, less pre- sentence custody. The defence submitted the equivalent of 456 days, less time served, was appropriate. The parties were apart on sentence quantum by approximately 24 days.

[27] When sentencing was argued, Mr. McCormack-Woolacoot had served 304 days. He has since served an additional 14 days, for a total of 318 days.

[28] Quantification of presentence custody served was contested. The defence sought 1.5:1 credit for each day in pre-sentence custody. The Crown objected, submitting he receive 1:1 credit for most presentence custody time.[^7] As of today’s date, the Crown’s position argues for an additional 118 days to be served. The defence advanced a position of time served, meaning the equivalent of 456 days.[^8]

APPLICABLE LEGAL PRINCIPLES

Legislative Framework

[29] This was not a case where additional credit was sought for the notoriously inhumane conditions at Toronto South Detention Centre. The defendant only sought Summers credit. Section 719 statutorily caps credit at 1.5 to 1 for each day served:

719 (3) In determining the sentence to be imposed on a person convicted of an offence, a court may take into account any time spent in custody by the person as a result of the offence but the court shall limit any credit for that time to a maximum of one day for each day spent in custody.
(3.1) Despite subsection (3), if the circumstances justify it, the maximum is one and one-half days for each day spent in custody.

Rationale of Summers Credit

[30] R. v. Summers, 2014 SCC 26 explained the historical, two-fold rationale behind granting enhanced credit. Only one, the quantitative rationale, applies to this case. As per Summers, supra, at paras. 23 and 25-27:

…the quantitative rationale for the practice of granting enhanced credit is to ensure that the offender does not spend more time behind bars than if he had been released on bail.
In practice, the "vast majority of those serving reformatory sentences are released on 'remission' ... at approximately the two-thirds point in their sentence", and only two to three percent of federal prisoners are not released either by way of parole or "statutory release": C. C. Ruby, G. J. Chan and N. R. Hasan, Sentencing (8th ed. 2012), at ss.13.38 and 13.39.
Because a sentence begins when it is imposed (s. 719(1)) and the statutory rules for parole eligibility and early release do not take into account time spent in custody before sentencing, pre-sentence detention almost always needs to be credited at a rate higher than 1:1 in order to ensure that it does not prejudice the offender.
A ratio of 1.5:1 ensures that an offender who is released after serving two thirds of his sentence serves the same amount of time in jail, whether or not he is subject to presentence detention. A higher ratio than 1.5:1 was therefore often used to account for other circumstances, including the loss of parole eligibility (i.e., the loss of the opportunity to be released after serving one third of the sentence).

[31] As Schreck J. said at para. 92 of R. v. Charley, 2025 ONSC 2490:

...it must be borne in mind that a credit of one and one-half days per day, if applied, has the effect of treating the offender as if he had been released after serving two-thirds of his sentence…

Denying Summers Credit in Jeyakanthan

[32] In the case at bar, the Crown relied upon R. v. Jeyakanthan, 2024 ONSC 1665. There, 1.5:1 credit for presentence custody was denied because the offender had committed offences, been released on bail, and offended again. His original time in presentence custody, the court found, should have presented a cautionary lesson against re-offending. Further offending proved it had not and as a result, the sentencing judge denied credit beyond 1:1. As per paras. 115-117:

The Supreme Court of Canada held in Summers that the 1.5:1 credit is not automatic, and need not be applied in every case. The Court held that a lower rate could be appropriate if the detention was a result of the offender’s own bad conduct, or if the offender is unlikely to obtain an early release or parole date (see R. v. Hussain, 2015 ONSC 7115 at paragraphs 78-80 and 119).
I agree entirely with the reasoning of Justice Edwards in Hussain and take the same position here. Janson was on a recognizance at the time he committed the offences now before me. Indeed, I have convicted him of two breaches of that recognizance. He spent some considerable time in custody at the Toronto South following his arrest on these charges. He was fully aware of the harsh conditions at the Toronto South, both before and after Covid, because he experienced them first-hand. I have given him full Summers credit and also Duncan credit for that period of time. He was then released on bail. While on that bail he breached its terms in a pretty egregious way in my view.
He did so knowing what the likely result would be if he was caught and knowing what the conditions of any inevitable incarceration would be. In those circumstances I am not prepared to provide any enhanced Summers credit, nor any credit under Duncan. He’s entitled to time served, which is 332 days.

[33] Respectfully, I disagree with this approach and this is why.

Jeyakanthan Was Not Persuasive

[34] First, the trial level decision relied upon in Jeyakanthan was overturned on appeal in 2018: see R. v. Hussain, 2018 ONCA 147 at paras. 17-22. To be clear, the Court of Appeal did not rule out bail breaches ever being used as “bad conduct” disentitling an offender from Summers credit. But the Court found the sentencing judge erred in doing so in that case. Further, at para. 21 the Court said:

In my view, where an offender is simultaneously being sentenced for breach charges and the charges that led to the recognizance or court order that was breached, it will ordinarily be preferable for the sentencing judge to deal with the breach by imposing a sentence commensurate with the seriousness of the breach. Such a sentence reflects the aggravating factor of committing an offence in breach of a court order and serves the purposes of sentencing, including deterrence, more directly and more appropriately than by denying enhanced credit for pre-sentence custody. In this case, the appellant was sentenced for the breach offences directly. He should not also be denied enhanced credit for the period of incarceration between the revocation of his bail and the imposition of his sentence due to the same breaches.

[35] Second and with all due respect, I found Jeyakanthan’s logic behind denying 1.5:1 credit somewhat untethered from Summers. Summers found that s. 719(3)(3.1)’s statutory intent ensures offenders denied bail were not punished more harshly than those with bail. In my view, the approach Jeyakanthan invites would have that unwanted effect.

[36] I recognize that Parliament explicitly excluded nothing from legitimately basing the denial of 1.5:1 credit. Indeed, the Supreme Court recently said as much, in R. v. J.W., 2025 SCC 16 at paras. 87-90:

In Summers, Karakatsanis J. explained that, in certain situations, enhanced credit will "often be inappropriate" (para. 48). Notably, "when long periods of pre-sentence detention are attributable to the wrongful conduct of the offender" (para. 48) or "when detention was a result of the offender's bad conduct" (para. 71), the offender will likely not be granted enhanced credit.
This appeal raises the following question: When an accused causes delay in their criminal proceeding, in what circumstances does this amount to "wrongful conduct"? ..
Lower courts have considered what constitutes "wrongful conduct", though often in obiter. …
Some cases have considered conduct other than delay to be "wrongful conduct" justifying the denial of enhanced credit. For example, some courts have considered whether factors considered in sentencing, such as aggravating factors, are relevant to the determination of enhanced credit (see, e.g., R. v. McBeath, 2014 BCCA 305, 314 C.C.C. (3d) 531; R. v. Boutilier, 2018 NSCA 65, 30 M.V.R. (7th) 31). Other cases query whether committing an offence while on bail or probation disqualifies an offender from obtaining enhanced credit (see, e.g., R. v. Morris, 2013 ONCA 223, 305 O.A.C. 47; R. v. Campbell, 2017 ONSC 26, at para. 62; R. v. Bonneteau, 2016 MBCA 72, 330 Man. R. (2d) 139, at para. 22; see also Ruby, at s.13.98). I am of the view that consideration of such circumstances is better left for another day, in cases where the relevant facts arise.

[37] Then the Supreme Court in J.W., after declining to explicitly interpret “wrongful conduct”, placed the onus of its proof on the Crown[^9] and referenced the need to interpret this term narrowly. The Court underscored the importance of an interpretation consistent with statutory intent and the principles of sentencing, such as parity.

[38] The following scenario runs counter to that statutory intent and those sentencing objectives:

PERSON A offends, gets bail, re-offends, is detained. Serves 30 real days in pre-sentence custody as between the two arrests. Fit sentence determined to be 30 days plus probation. But because they offended while on bail, TS is credited at 1:1, meaning no credit for loss of early release. Actual time served is thus 30 days.
PERSON B offends in the same way as Person A, is immediately released on bail, again re-offends in the same way as Person A, is immediately released again. Fit sentence determined to be 30 days plus probation. Person B, who also offended in the same way while on bail, goes into custody and serves 20 days before early release.[^10]

[39] Person B’s ability to secure bail twice meant they served less actual time in jail than Person A did. Such a result does not express equity: R. v. Kovich, 2016 MBCA 19 at para. 106 and R. v. Safarzadeh-Markhali, 2016 SCC 14 at paras. 66-67. Additionally, and as the Supreme Court pointed in Summers at paras. 65-67, the playing field for obtaining bail is not always even:

…it is difficult to see how sentences can reliably be "proportionate to the gravity of the offence and the degree of responsibility of the offender" (s. 718.1) when the length of incarceration is also a product of the offender's ability to obtain bail, which is frequently dependent on totally different criteria.
Judicial interim release requires the judge to be confident that, amongst other things, the accused will neither flee nor reoffend while on bail. When an accused is able to deposit money, or be released to family and friends acting as sureties (who often pledge money themselves), this can help provide the court with such assurance. Unfortunately, those without either a support network of family and friends or financial means cannot provide these assurances. Consequently, as the intervener the John Howard Society submitted, this means that vulnerable and impoverished offenders are less able to access bail.
For example, Aboriginal people are more likely to be denied bail, and make up a disproportionate share of the population in remand custody.6 A system that results in consistently longer, harsher sentences for vulnerable members of society, not based on the wrongfulness of their conduct but because of their isolation and inability to pay, can hardly be said to be assigning sentences in line with the principles of parity and proportionality. Accounting for loss of early release eligibility through enhanced credit responds to this concern.

[40] Denying 1:1 credit because of bail breaches also poses a real risk of punishing one breach twice. See R. v. Hussain, supra at paras. 19-21 and R. v. Boutilier, 2018 NSCA 65:

…while the fact that an offence was committed on bail may be taken into account in determining the appropriate amount of pre-sentence credit, the extent to which the breach has already been punished must also be considered: see R. v. Colt, 2015 BCCA 190, 324 C.C.C. (3d) 1, at paras. 24-27. To impose an eighteen-month sentence for the breaches, and then further deny the appellant the usual credit for pre-sentence custody on the basis of the same breaches would, in effect, punish him twice for the same misconduct…

PRESENTENCE CUSTODY CREDITED

[41] In the case at bar, there was no evidence of institutional misconduct or to suggest Mr. McCormack-Woolacoot would be ineligible for early release. The “wrongful conduct” relied upon was his re-offending behaviour while on release orders.

[42] In my view, the objectives of parity, fairness, and transparency are best met by imposing either specific sentence for breaches or using breaches to aggravate and increase another sentence. I thus decline to impose 1:1 credit for the time spent by Mr. McCormack-Woolacoot in presentence custody. I have credited of pre-sentence custody used at 1.5:1.

SENTENCE IMPOSED

[43] As stated above, there was but twenty-four days between the Crown and defence positions when sentencing was argued. I agree that a sentence in this range is fit and would express the necessary sentencing objectives.

[44] I found aggravating factors to include the breach of the defendant’s conditional sentence order and probation order, the various breaches of Mr. McCormack-Woolacoot’s bail orders, the victim impact evidence of trauma, impact on victims who did not submit statements, the other offences disclosed by the facts, and his criminal record.

[45] I found mitigating factors to include Mr. McCormack-Woolacoot’s guilty plea and decision to spare the court system multiple trials, his troubled background including disconnection from his culture,[^12] his addiction to a Schedule I drug and its connection to some offending, and the rehabilitative potential he so clearly has.

[46] After weighing the aggravating and mitigating factors, I concluded a global sentence of 460 days is fit. When pre-sentence custody of 307 days is calculated on a 1.5:1 basis, it is the equivalent of 460 days.

[47] In other words, Mr. McCormack-Woolacoot has already served the custodial part of his sentence. I will allocate specific sentences for each specific offence,[^13] but globally they total 460 days jail.

[48] Mr. McCormack-Woolacoot will be placed on two years of probation [conditions omitted from written reasons]. A DNA order and a s. 109 order will issue. The victim fine surcharge is waived.

Released: July 4, 2025
Signed: Justice H. Pringle

[^1]: 307 calendar days x 1.5 = 460 days.
[^2]: September 29, 2023.
[^3]: March 8, 2024.
[^4]: June 29, 2024.
[^5]: November 15, 2024.
[^6]: CPIC shows a 2014 Fail to Comply with Probation conviction, which suggested the imposition of a preceding adult probation order but which was not reflected on CPIC.
[^7]: In submissions, the Crown agreed 1.5:1 credit should be imposed for 88 days, which on that calculus totaled the equivalent of 132 days. The remaining 216 days he served after being released and eventually detained was, on the Crown position to be credited as 216 days.
[^8]: This was as of the date of sentencing submissions, when defence sought equivalent of 456 days and Crown sought equivalent of 480 days. Another 14 days passed after judgment reserved. I did not use most of this additional time, on my assessment of a fit sentence guided by restraint.
[^9]: See also R. v. Parker, 2024 ONCA 591 at para. 55.
[^10]: I am ignoring other nuances in Person B’s scenario, such as the brief time prior to arrest counting as pre- sentence custody, solely to keep the hypothetical math simple. Even were that factored in, the inequity between the two results remains the same.
[^11]: In the context of a constitutional challenge to an aspect of s. 719, as it originally read.
[^12]: There was no evidence of the defendant’s indigenous background, except his disconnection from it and history in the Crown ward system. No Gladue report was requested.
[^13]: See informations.