ONTARIO COURT OF JUSTICE

CITATION: R. v. Da Rosa, 2026 ONCJ 207

DATE: April 9, 2026

COURT FILE No.: Bradford #24-81301502 & 24-81300863

BETWEEN:

HIS MAJESTY THE KING

— AND —

JONHATTAN DA ROSA

Before Justice C.A. Brannagan

Heard on 6 January & 26 March 2026

Reasons for Sentence delivered on 9 April 2026

Ms. A. Brown....................................................................................... counsel for the Crown

Mr. P. Sherman .......................................................................... counsel for the Defendant

C.A. Brannagan J.:

OVERVIEW

1. Jonhattan Da Rosa appeared before me on January 6, 2026, and pleaded guilty to two counts of fraud under $5,000, contrary to s. 380(1) of the Criminal Code. The Crown elected to proceed by summary conviction. I ordered a pre-sentence report at Counsel’s request, and the matter was last before me for submissions on sentence on March 26, 2026. These are my reasons for sentence.

CIRCUMSTANCES OF THE OFFENCE

2. Both offences to which Mr. Da Rosa has pleaded guilty arose from him advertising and providing legal services as a licensed paralegal. He was not qualified to do so; he was not licensed by the Law Society of Ontario. Mr. Da Rosa was an illegal practitioner.

3. In February 2023, John Barnes hired Mr. Rosa to represent him in a Small Claims Court matter after seeing him recommended on a local Facebook group. Mr. Da Rosa advertised himself as a licensed paralegal affiliated with “Oaktree Group Legal Services”, a defunct paralegal services firm he had worked at as a clerk.

4. Mr. Barnes paid Mr. Da Rosa $2,486.00 on February 16, 2023, and another $591.50 on February 19, 2023, both through e‑transfer. Mr. Da Rosa issued fake receipts on Oaktree letterhead.

5. Mr. Da Rosa told Mr. Barnes in September 2023 that he had “won” his Small Claims case but provided no proof, nor had he ever filed any meaningful documents beyond a single filing at the Barrie Small Claims Court.

6. Mr. Barnes later learned from Jennifer Valdes, the former owner of Oaktree, that although Mr. Da Rosa had previously worked for her as an assistant, he never had authority to accept client funds, and she was not involved in his matter.[^1]

7. Mr. Da Rosa also held himself out to be a licensed paralegal to Jennifer Healey. In March 2023, she hired him for a landlord‑tenant matter and paid him $2,500.00 via e‑transfer. He provided legal advice and issued fake invoices. He encouraged her to refer friends to him for a discount. Ms. Healey eventually became suspicious that Mr. Da Rosa was not a licensed paralegal.

8. Police confirmed Ms. Healey’s suspicions. They contacted the Law Society of Ontario (LSO) in October 2023, learning that Mr. Da Rosa did not hold a paralegal licence during February–March 2023.

9. In fact, he had never been licensed as a paralegal by the LSO.

CIRCUMSTANCES OF THE OFFENDER / PRE-SENTENCE REPORT (PSR)

10. The purpose of a PSR is to provide the court with information about “the offender’s age, maturity, character, behaviour, attitude and willingness to make amends.”: Criminal Code, s. 721(1) & (3); R. v. Green, 2006 ONCJ 364, at paras. 12-13.

11. The PSR was made Exhibit #2. Mr. Sherman made two brief qualifications to it: (1) the referenced motor vehicle collision occurred in 2022, not 2023, and (2) Mr. Da Rosa is not receiving accident benefits. A summary of the PSR follows.

12. Mr. Da Rosa is a 48‑year‑old man who immigrated to Canada from Uruguay at age 12. His 27‑year marriage ended in 2024. He and his former spouse share three adult children, with whom Mr. Da Rosa has little contact. He now lives in rented accommodation in Alliston, relies on social assistance, and has limited family and social supports.

13. Although he worked for many years as a law clerk, and for a few years as a paralegal – before the Law Society began regulating the profession in 2007 – he was never properly qualified as a licensed paralegal.

14. He and his family moved to Florida in 2003. When Mr. Da Rosa re-entered Canada in 2011 for a social event, he was arrested on an outstanding warrant for historical fraud charges dating back to 2002. He was convicted of those fraud charges and sentenced, as a first offender, to an 18-month conditional sentence.

15. He attended a private college between 2012-2014, studying to become an immigration consultant and paralegal assistant. He applied for licensure with the LSO but was denied that privilege in 2021 because of his criminal record.

16. A 2022 car accident precipitated a significant decline in his mental health, including major depressive disorder, multiple anxiety disorders, OCD, cannabis‑induced psychosis, and ADHD. He has undergone several medication changes, reported three suicide attempts, and receives regular psychiatric and psychological care.

17. Mr. Da Rosa acknowledges longstanding addictions – to cocaine, alcohol, and gambling – which contributed to the breakdown of his marriage and estrangement from his children. He expressed remorse for the offences, though he partially attributes his conduct to the post‑accident deterioration in his mental state. He is currently unemployed and awaiting resolution of a civil claim related to the collision, believing that a settlement will allow him to make restitution.

18. The PSR author concludes that Mr. Da Rosa presents both risk factors – including financial instability, social isolation, mental‑health vulnerabilities, and a history of deception – and rehabilitative factors – including treatment engagement, sobriety, and past compliance with community supervision.

POSITIONS OF THE PARTIES

Crown Submissions

19. The Crown seeks a sentence of six months of custody followed by 18 months of probation. The Crown proposes that restitution be paid in full to both complainants, that the offender be required to participate in mental‑health counselling as directed, that he be prohibited from rendering or advertising any legal services, and that he have no contact or association with the victims.

20. The Crown emphasizes that these offences represent a serious breach of trust. Mr. Da Rosa falsely held himself out as a licensed paralegal and exploited individuals seeking legal assistance. In support of its position, the Crown highlights Mr. Da Rosa’s prior fraud convictions from 2011, as well as LSO findings reflecting a long‑standing pattern of misrepresenting himself as a qualified legal professional while engaging in related misconduct.

21. The Crown argues that the sentencing objectives of denunciation and both general and specific deterrence must be given significant weight given the repetitive and deliberate nature of the deceit, the impact on the victims, and the broader public‑interest concern of maintaining confidence in the integrity of legal services.

22. Overall, the Crown submits that a custodial sentence is necessary to reflect the gravity of the offences and the offender’s pattern of fraudulent behaviour.

Defence Submissions

23. Defence submits that a conditional sentence order (CSO) of 6-12 months is appropriate, given Mr. Da Rosa’s personal circumstances and mental‑health challenges. Counsel emphasizes that his client is committed to paying full restitution once he receives an expected personal‑injury settlement.

24. Mr. Sherman highlights his client’s unemployment, reliance on Ontario Works, and unstable housing history. He stresses the deterioration in Mr. Da Rosa’s mental health after the 2022 motor‑vehicle collision, filing letters from Mr. Da Rosa’s psychological and psychiatric treatment providers (Exhibits #3 and 4).

25. Counsel argues that Mr. Da Rosa has lost his career, family relationships, and financial stability following the collision, and is making genuine efforts at rehabilitation, including regular mental‑health treatment and abstention from substances other than medically‑advised cannabis for sleep.

26. If the Court finds a ‘true’ custodial sentence unavoidable, defence seeks a 90‑day intermittent sentence followed by probation, with community service if appropriate.

27. Mr. Sherman challenges the Crown’s position on his client’s risk for recidivism by noting that the accused complied with the terms of his previous 2011 CSO and has no allegations of breach in connection with the present charges, suggesting Mr. Da Rosa is capable of safely serving a community‑based sentence.

28. Mr. Sherman distinguishes the older misconduct highlighted in the Law Society’s findings, emphasizing that some of the conduct occurred at a time when a paralegal licence was not required, and that Mr. Da Rosa had genuinely sought to become licensed but was ultimately denied due to his criminal record.

THE LAW

The Offence of Fraud

29. Criminal fraud is a “deliberately practiced fraudulent act which, in the knowledge of the accused, actually puts the property of others at risk”: R. v. Plange, 2019 ONCA 646, at para. 25.

30. Fraud is established where the Crown proves that the defendant engaged in a dishonest act – whether by deceit, falsehood, or other fraudulent means – and that this conduct caused a deprivation or exposed the victim’s financial interests to a risk of loss. The mental element of the offence requires proof that the accused intended to deceive or otherwise act fraudulently: Plange, supra, at para. 24.

31. When the Crown elects to proceed by summary conviction, as it has here, the maximum term of imprisonment is two years: s. 380(1)(b)(ii) & s. 787(1).

32. Consecutive sentences for multiple offences are warranted where those offences reflect distinct wrongs, subject to the principle of totality: s. 718.2(c); s. 718.3(4)(b)(i); R. v. Al-Enzi, 2025 ONCA 485, at para. 8.

33. Consequently, Mr. Da Rosa faces up to four years in prison for these two offences.

Relevant Sentencing Case Law

34. While no two fraud cases are directly comparable, the jurisprudence is consistent in treating frauds committed through the misrepresentation or abuse of legal or quasi-legal authority as especially aggravating. Courts have repeatedly emphasized that offences exploiting the institutional trust associated with legal services undermine public confidence in the administration of justice and generally warrant custodial sentences, even where the offender has no prior criminal record.

35. Ontario courts have imposed jail terms in cases involving paralegals, law clerks, and other legal-sector actors who engaged in deliberate and sustained deception by holding themselves out as authorized to provide legal services or manage legal funds: see R. v. Finlan, [2007] O.J. No. 5791 (Ct. Jus.) (two years less a day); R. v. Castro, 2010 ONCA 718 (23 months); R. v. Piccinini, 2018 ONCA 433 (12 months); R. v. Booker, 2024 ONCA 181 (18 months); and R. v. Chevis, 2026 ONCJ 126 (four years). These decisions demonstrate that the decisive aggravating factor is not strictly the quantum of loss, but the calculated invocation of legal authority to facilitate fraud, and the resulting harm to the repute of the justice system.

36. Defence relies on R. v. Noel, [2002] O.J. No. 5591 (Ct. Jus.), where a CSO was imposed for a breach of trust offence by a lawyer. But Ms. Noel had no prior criminal record, her conduct was an isolated and out-of-character aberration, and there was a clear causal connection between her mental health condition and the offence. Noel is distinguishable from Mr. Da Rosa’s case for those reasons.

Sentencing Objectives – Purpose and Principles of Sentencing

37. The fundamental purpose of sentencing is to protect society and to promote respect for the law through just sanctions that denounce unlawful conduct, deter crime, facilitate rehabilitation, protect the public, and encourage offenders to acknowledge harm: s. 718. The relative weighting of these principles depends upon the nature of the crime and the individual circumstances of the offender.

The Fundamental Principle of Proportionality

38. All sentencing starts with the principle that a fit and appropriate sentence is one that is proportionate to the gravity of the offence and the degree of responsibility of the offender: s. 718.1; R. v. Parranto, 2021 SCC 46, at para. 10.

Other Relevant Sentencing Objectives

39. There are additional sentencing objectives that courts must consider in arriving at a just and appropriate sentence for the individual offender. The following sentencing principles are engaged on this record:

i. the effect of a guilty plea as a sign of remorse;

ii. the exercise of restraint, s. 718.2(d) and (e);

iii. the principle of totality, s. 718.2(c);

iv. abuse of a position of trust or authority in relation to the victims: s. 718.2(a)(iii);

v. the jump principle: R. v. Wallace, 2026 ONCA 105, at para. 4;

vi. the parity principle, s. 718.2(b).

40. While the principle of sentencing parity remains a salient consideration, and is itself “an expression of proportionality”, no two cases are alike, and “[i]ndividualization is central to the proportionality assessment. Whereas the gravity of a particular offence may be relatively constant, each offence is ‘committed in unique circumstances by an offender with a unique profile’”: Parranto, supra, at para. 12.

41. The evaluation of an individual offender’s moral culpability is assessed by weighing the aggravating and mitigating circumstances relating to the offence and the offender: s. 718.2(a); R. v. Gilmore, 2025 ONCA 517, at para. 35.

42. An offender’s sentence will be pushed higher up or lower down the scale depending upon the relative importance of the mitigating and aggravating features of the case: R. v. Nasogaluak, 2010 SCC 6, at para. 43.

Mitigating Circumstances

43. I have considered the following factors in assessing mitigation:

i. Mr. Da Rosa pleaded guilty to these offences, saving the time and expense of a trial. The court was aware of his intention to resolve this case in July of 2025, when the matter was pre-tried before me. The only dates scheduled were those for the guilty plea, submissions, and sentencing.

ii. Mr. Da Rosa expressed remorse for his crimes. Sincere remorse is a mitigating factor where it reflects insight and an acceptance of responsibility. While I do accept Mr. Da Rosa’s guilty plea as an expression of his remorse, its mitigating weight is attenuated by his suggestion that the motor vehicle accident he was involved in contributed to the commission of these crimes. This self-assessment overlooks the fact that his conduct forms part of a longer-standing pattern of deliberate deception, as shown by his 2011 convictions and the Law Society’s 2021 findings that he lacked the good character necessary for admission as a licensed paralegal: Da Rosa v. Law Society of Ontario, 2021 ONLSTH 46.[^2]

iii. With that said, I accept that Mr. Da Rosa suffers from various mental health challenges resulting from the 2022 motor vehicle accident. An offender’s mental health challenges may mitigate and lower their moral blameworthiness when there is a causal connection between the mental health challenges and the offences at issue. While there is evidence before this court that Mr. Da Rosa suffers from mental health issues, the letters from his psychologist and psychiatrist each post-date his offending and neither asserts nor establishes any causal connection between his mental health difficulties and the commission of these offences: R. v. Lojovic, 2025 ONCA 319, at paras. 46-50; Gilmore, supra, at para. 52.

iv. I also accept the “…potentially harsher impact of incarceration on an offender with significant mental health and cognitive limitations. Such vulnerabilities may render imprisonment more severe and must be taken into account”: R. v. Purvis, 2026 ONCA 187, at para. 37. However, I find that Mr. Da Rosa’s personal health challenges are not such that would render a custodial sentence either impractical or unusually cruel.

v. It is not mitigating that Mr. Da Rosa had completed related studies, worked as a paralegal decades earlier, or that he worked in a legal services firm in the years before he engaged in this deception: s. 380.1(2).

vi. Mr. Da Rosa has expressed his willingness to pay restitution. That he has not made any effort whatsoever to do so in the three years since these offences were committed is not aggravating, but I do note it as the absence of what would otherwise have been a favourable mitigating factor.

Aggravating Circumstances

44. I find the following aspects to be aggravating:

i. This is not the first time that Mr. Da Rosa has engaged in criminal fraud. His 2011 convictions for fraud under $5,000 and fraud over $5,000 related to him abusing his position as a paralegal in 2002 and 2003, by cashing someone else’s cheque and by defrauding an insurance company by staging an accident. He was convicted of those offences years later only because he had been living illegally in Florida until 2011: Da Rosa v. Law Society of Ontario, 2021 ONLSTH 46.

ii. The offence had an impact on the victims given their personal circumstances, including their financial situations, as none of the funds defrauded were recovered: s. 718.2(a)(iii.1).

iii. Mr. Da Rosa failed to comply with a licensing requirement that is applicable to the work of a paralegal, since he held himself out to be and offered legal advice as though he was a licensed paralegal, when he had been denied that very privilege years earlier by the LSO: s. 380.1(1)(e).

iv. His fraudulent conduct ended only because it was discovered. There is nothing to suggest he would have stopped had he not been caught.

v. By impersonating a licensed paralegal and defrauding members of the public, Mr. Da Rosa undermined confidence in the administration of justice. His abuse of the appearance of legal authority to facilitate his deception unfairly discredits those who are duly qualified to practice in the legal profession.

45. Given these circumstances, I find Mr. Da Rosa’s offending to be grave, and his moral culpability to be high. I find the paramount sentencing principles at play to be denunciation, specific and general deterrence, and the protection of the public. Rehabilitation is important, but it is subordinate in this case.

Conditional Sentence Orders

46. Conditional sentence orders are set out at section 742.1, which provides:

If a person is convicted of an offence and the court imposes a sentence of imprisonment of less than two years, the court may, for the purpose of supervising the offender’s behaviour in the community, order that the offender serve the sentence in the community […] if

(a) The court is satisfied that the service of the sentence in the community would not endanger the safety of the community and would be consistent with the fundamental purpose and principles of sentencing set out in sections 718 to 718.2;

(b) the offence is not an offence punishable by a minimum term of imprisonment […]

47. I find that a term of imprisonment of less than two years is appropriate in this case. I also accept that the offence of fraud under $5,000 is not an offence punishable by a minimum term of imprisonment. The crimes to which Mr. Da Rosa has been found guilty would make a CSO an available sentence in this case.

48. This leaves open the question of whether the court can be satisfied that the public safety would not be endangered by the offender serving his sentence in the community, and whether such a sentence would be consistent with the purpose and principles set out in sections 718 to 718.2. Satisfaction of s. 742.1(a) is a condition precedent to the imposition of a conditional sentence.

49. To assess the potential risk the offender poses to the public, if they were to serve their sentence in the community, two factors must be considered: (1) the risk of the re-offending; and (2) the gravity of the damage that could ensue in the event of re-offence. As the Supreme Court has stated: “If the judge finds that there is a real risk of re-offence, incarceration should be imposed”: R. v. Proulx, 2000 SCC 5, at para. 69.

50. I find that Mr. Da Rosa presents a real risk of reoffending in a like manner in the future. Such offending would further undermine the repute of the administration of justice and the public’s confidence in expecting that only those legal practitioners who are duly licensed by the Law Society can hold themselves out as being properly qualified to render legal services.

51. I find that a conditional sentence order would be contrary to the purpose and principles of sentencing.

Disposition

52. In determining a fit sentence, I have considered and weighed all relevant aggravating and mitigating factors, both personal to Mr. Da Rosa and relating to the offences themselves. I have not elevated any single factor as determinative. Having regard to the seriousness and repetitive nature of the offences, the abuse of the appearance of legal authority, the harm caused to the complainants, and the offender’s personal circumstances, mental health challenges, guilty plea, and expressions of remorse, I am satisfied that a custodial sentence is proportionate to the gravity of the offences and the offender’s degree of responsibility. In my view, it represents the least intrusive sanction capable of achieving the fundamental purposes and principles of sentencing in this case.

53. I sentence Jonhattan Da Rosa to a period of incarceration of six months for each of these two offences, one concurrent to the other.

54. To assist with rehabilitation and reintegration into the community, the carceral portion of this sentence will be followed by a period of probation for 18 months, with the following terms:

i. Report to probation within three business days of your release from custody, and report thereafter as and when directed by your probation officer;

ii. Take any counselling as directed by your probation officer;

iii. Sign all necessary releases to permit your probation officer to monitor your enrolment in, attendance at, and completion of any directed counselling;

iv. Do not contact or communicate, directly or indirectly, through any physical, electronic or other means, with John Barnes or Jennifer Healey;

v. Do not attend within 100m of any place you know Mr. Barnes or Ms. Healey to live, work, study, worship, frequent, or otherwise know them to be;

vi. Do not offer or provide any legal advice or legal services, of any kind, or engage in any marketing or advertising, in any form, for any legal services.

55. Mr. Da Rosa will make restitution in the amounts of $3,077.50 to Mr. Barnes, and $2,500.00 to Ms. Healey, as free-standing restitution orders: s. 738(1)(a).

56. The victim fine surcharge is waived, pursuant to s. 737(2.1)(a).

Released: 9 April 2026.

Signed: Justice C.A. Brannagan

[^1]: Parenthetically, I note that Ms. Valdes had legal troubles of her own, involving Mr. Da Rosa, which resulted in the surrendering of her paralegal licence: Law Society of Ontario v. Valdes Trigo, 2025 ONLSTH 115.

[^2]: I rely on Mr. Da Rosa’s Law Society findings only to inform my assessment of his background and character as it relates to his future risk of re-offending, insofar as those findings support a pattern of deceptive behaviour in the legal-services setting: R. v. Di Paola, 2025 SCC 31, at para. 41; R. v. Angelillo, 2006 SCC 55, at paras. 18, 22, 30; R. v. Edwards, 2001 24105 (ON CA), [2001] O.J. No. 2582 (C.A.), at paras. 63-64.