Palmer J
20250801- R v. Simpson (Orlando Roy). - Ind.108/2024. Coram: Palmer J. (Actg.). - Sentence Judgment. IN THE GRAND COURT OF THE CAYMAN ISLANDS 1 CRIMINAL SIDE 2 3 Neutral Citation Number: [2025] CIGC (Crim) 75 4 IND. No: 108/2024 5 6 7 REX 8 9 V 10 11 ORLANDO ROY SIMPSON 12 13 14 Appearances: Mr. Orrett Brown for the Crown 15 16 Ms. Crister Brady for the Defendant 17 18 Before: Justice Dale Palmer (Actg.) 19 Submissions heard: 4th July 2025 20 21 Sentence Judgment: 1st August 2025 22 23 24 HEADNOTE 25 Criminal Law – Rape - Assault – Threats to Kill – Application of the Cayman 26 Islands Sentencing Guidelines 27 28 SENTENCE JUDGMENT 29 30 31 32 33 20250801- R v. Simpson (Orlando Roy). - Ind.108/2024. Coram: Palmer J. (Actg.). - Sentence Judgment. COMPLAINANT’S ANONYMITY 1
By virtue of section 31 of the Criminal Procedure Code (2021 Revision) (‘CPC’) 2 the publishing or broadcasting of the matter in a way to cause the public to identify 3 the complainant is restricted as follows: 4 "Anonymity of complainants in rape etc. cases: 5 31. (I) After a person is accused of a rape [ etc.] offence, no matter likely 6 to lead members of the public to identify a woman as the woman against 7 whom the offence is alleged to have been committed shall be published 8 in a written publication available to the public or be broadcast, except 9 as authorised by a direction of the court. 10 (2) … 11 (3) … 12 (4) … 13 (5) If any matter is published or broadcast in contravention of 14 subsection (I), the following persons 15 (a) in the case of a publication in a newspaper or periodical, the 16 proprietor, editor and publisher of the newspaper or periodical; 17 (b) in the case of any other publication, the person who publishes it; 18 (c) in the case of a broadcast, any person having functions, in relation 19 to the programme in which it is made, corresponding to those of an 20 editor of a newspaper, 21 commit an offence and are each liable on summary conviction to a fine 22 of one thousand dollars. " 23
As indicated at the time of delivery of the verdict judgment that I took the view that 24 the charges against the Defendant fall within this section and therefore my prior 25 order that there should be no publication in whatever form of the identity of the 26 victim in this case. Accordingly, the identity of the victim has been anonymised. 27 28 BACKGROUND 29
The Defendant was convicted on 28 March 2025, after a trial by Judge Alone was 30 held in January 2025 in relation to Indictment 108 of 2024 which contained three 31 counts as follows: 32 • Count 1 – Assault Causing Actual Bodily Harm: Contrary to section 216 33 of the Penal Code (2024 Revision). 34 20250801- R v. Simpson (Orlando Roy). - Ind.108/2024. Coram: Palmer J. (Actg.). - Sentence Judgment. • Count 2 – Rape: Contrary to section 127 of the Penal Code (2024 1 Revision). 2 • Count 3 – Threats to Kill or Cause Serious Harm: Contrary to section 3 88C of the Penal Code (2024 Revision). 4 5
The facts relating to Count 1 emanate from an altercation between the parties in July 6 2024 during which the Defendant assaulted the victim resulting in injuries to her face 7 and pain to her breast. The Defendant accused her of infidelity, a vein that repeatedly 8 runs throughout this case, and spat on her during the incident. When the Defendant 9 left the home to proceed abroad, the victim left the Defendant’s home and relocated 10 to other premises, the location of which she did not share with the Defendant. This 11 assault was the subject of Count 1. 12 13
Count 2 and Count 3 relate to events that occurred on the evening of 30 August 2024. 14 After the July incident the victim continued to speak to with the Defendant via the 15 telephone and had been promising to return. It was evident from her testimony that 16 she had conflicting emotions regarding the Defendant but was fearful about 17 resuming the relationship. He was still very integrated into her life – with a close 18 relationship with her boss, her father and brother and he was the reason she had come 19 to the Cayman Islands to begin with. She continued to promise that she would return 20 and gave the impression that she had been living with her boss, both of which he 21 discovered were untrue. 22 23
When he discovered that she had deceived him as to where she was living, the 24 Defendant invited assistance from a friend to determine where the victim was living. 25 He hid in the car of his friend as they patrolled the vicinity of the victim’s route 26 home. When she was seen, she was trailed home and he did further investigation and 27 discovered that the property was owned by an individual about whom the two had 28 had arguments previously. 29 30
On 30 August 2024 he waylaid her near where she would disembark from public 31 transportation after work and she hid inside an establishment - she having caught on 32 to the fact that she was being followed. The Defendant stated at trial that he got 33 frustrated when he saw that she had stayed way too long inside the establishment 34 and drove with his friend to where he had previously discovered the victim was 35 living. He waited in the darkness and approached her from behind armed with a sharp 36 20250801- R v. Simpson (Orlando Roy). - Ind.108/2024. Coram: Palmer J. (Actg.). - Sentence Judgment. object that he placed at her neck and threatened to do her serious harm. Mindful of 1 her ‘special needs’ 14-year-old son, and in fear for her life, she allowed the 2 Defendant into the apartment. On entering the apartment, the Defendant discovered 3 that TM had packed nothing to return to ‘home’ to him, despite her assurances, which 4 also confirmed his suspicion that she had found someone else. 5 6
The Defendant demanded sex from the victim, which she said she submitted to 7 because of the earlier threats. From her evidence it was clear that she saw this as an 8 escalation as, despite prior physical altercations, she did not know him to carry or 9 use knives in the past. 10 11
After he had sexual intercourse with her without her consent, he spent the night at 12 her apartment during which he took charge of her cellular phone which he monitored 13 and inspected to obtain proof of her suspected infidelity. He also called her brother 14 complaining of all that had transpired. She remained with him for the weekend after 15 they went to his home. On the following Monday morning, she went to the police 16 and reported the matter. The Defendant was arrested and later charged. 17 18
After the charge, the Defendant and different members of his family contacted the 19 complainant by telephone, urging her to bring an end to the proceedings. At that time 20 the complainant was still undergoing counselling for the incidents that are the subject 21 of the charges. She says she capitulated and agreed that she had not told the police 22 that the Defendant had raped her and threatened her with the knife or sharp object. 23 She maintained however at trial, and it was accepted, that she did so to get them to 24 stop harassing her. The Defendant was convicted of all three counts on the 25 indictment. 26 27
A Social Inquiry Report (SIR) and a Victim Impact Report (VIR) were ordered after 28 the Defendant was convicted, to assist the court in the process of sentencing. 29 30 VIR 31
TM indicated that she is traumatised due to the incident and expressed that she feels 32 very afraid of the Defendant. She revealed that she was deeply affected and had lost 33 weight due to the experience. She expressed that she has been left paranoid and 34 experienced anxiety attacks. She said she was constantly looking over her shoulder 35 20250801- R v. Simpson (Orlando Roy). - Ind.108/2024. Coram: Palmer J. (Actg.). - Sentence Judgment. and living in fear. TM asserted that the ordeal has resulted in a change to her daily 1 life. 2 3 SIR 4
According to the SIR, the Defendant is a 46-year-old Jamaican national who has 5 resided intermittently in the Cayman Islands since 1999 and most recently returned 6 in 2017 for employment in the construction industry. At the time of his remand, he 7 was gainfully employed under a work permit that expired in June 2025. 8 9
The Defendant’s early life in Jamaica was marked by significant hardship and abuse, 10 in particular severe physical abuse at the hands of his father. According to the report 11 the Defendant said he would be struck by garage tools and was regularly kept out of 12 school to assist with chores and vehicle repairs. Because of this unstable and 13 traumatic upbringing, he exited formal education at grade eight to enter the world of 14 work at the age of 16. He is only functionally literate but managed to learn carpentry 15 and has maintained steady employment as a mason for close to three decades. He 16 has no known prior convictions, either in this jurisdiction or in Jamaica. 17 18
The Defendant has three adult children and maintains what appears to be a close 19 relationship with his family, particularly his sister and mother, both of whom 20 provided supportive character references. Several reference letters described him as 21 kind-hearted, family-oriented, and helpful to others. Prior to his remand into custody 22 upon conviction, he reported having steady earnings and maintained his household 23 expenses with support from his adult son, with whom he co-habited for a period. 24 25
The Defendant characterised his relationship with TM as being “on-again/off-again” 26 and spanning approximately twelve years - beginning in Jamaica and continuing in 27 the Cayman Islands. He acknowledged being unfaithful during their relationship – 28 seeing up to four women concurrently with TM. While he initially denied any history 29 of domestic violence, he acknowledged that the RCIPS had been contacted in 30 circumstances where he refused to return TM’s cell phone – which is an example of 31 the type of controlling behaviour that appears to have characterised their 32 relationship. 33 34 35 20250801- R v. Simpson (Orlando Roy). - Ind.108/2024. Coram: Palmer J. (Actg.). - Sentence Judgment.
In relation to the present offences the Defendant has continued to maintain his 1 innocence and insisted that the sexual interaction with TM was “make-up sex” 2 following a period of estrangement from her. The Defendant reiterated his view that 3 the complainant’s report was motivated by a desire to preserve another relationship 4 and/or to retaliate for his infidelity. He denied threatening the complainant or 5 confining her against her will and maintained a sense of disbelief at the charges. 6 These comments echoed sentiments the accused expressed at trial; especially 7 regarding TM’s motive to lie and his suspicion about her involvement in another 8 relationship. 9 10
The SIR refers to a tendency by the Defendant to minimise the seriousness of the 11 offences, and to shift blame from himself onto TM. The assessing officer noted that 12 the defendant appeared unable to appreciate the trauma experienced by TM. He 13 complained of the stress, anxiety and shock he experienced due to the court 14 proceedings, which he believes have their true genesis in TM’s malicious feelings 15 especially resulting from his repeated indiscretions. The offender was assessed as 16 having a low-risk rating for future sexual and violent offending, but a medium risk 17 for repeating the anti-social pattern. 18 19
The report points out several aggravating features, including: 20 • The offender's denial of responsibility despite compelling evidence and a finding 21 of guilt; 22 • His lack of empathy at the victim’s experience; 23 • His history of controlling and emotionally abusive conduct within the 24 relationship; 25 • The calculated nature of the offence, which involved tracking her down, 26 threatening and confining the victim. 27 28
Mitigating features highlighted in the SIR were as follows: 29 • He has no previous criminal convictions and was assessed as being at a low risk 30 for future offending; 31 • He has maintained lawful employment for many years and contributed 32 meaningfully to his household and extended family; 33 • He suffered significant abuse and deprivation during his formative years, which 34 may have impaired his emotional development and capacity to form healthy 35 intimate relationships; 36 20250801- R v. Simpson (Orlando Roy). - Ind.108/2024. Coram: Palmer J. (Actg.). - Sentence Judgment. • His support network, particularly from his immediate family, remains intact, and 1 several references attest to his otherwise non-violent nature in prior 2 relationships. 3 4
The report recommends that the defendant would benefit from rehabilitative 5 interventions, including the Sex Offender Treatment Programme (SOTP) and the 6 Interpersonal Relationship Enhancement and Awareness Programme (IREAP). It 7 further suggests that a Sexual Harm Prevention Order (SHPO) be considered, and 8 that any sentence should include restrictions prohibiting contact with the victim, 9 whether directly or indirectly, and maintaining a minimum distance of 100 feet from 10 her. 11 12 ANTECENDENT HISTORY 13 14
The defendant is now 46 years old and has no prior offences recorded against him in 15 Jamaica or in the Cayman Islands. 16 17 CROWN SUBMISSIONS 18 19
The Crown submits that the custodial threshold is clearly passed in respect of all 20 three offences for which the defendant was convicted. The serious nature of the 21 offences, in particular, that of rape, it was submitted, warrants an immediate 22 custodial sentence to reflect the gravity of the offences and to take account for the 23 sentencing principles of deterrence, punishment, and prevention. 24 25
Rape, it was submitted falls is under Category 2 Harm and Category A Culpability, 26 based on the Cayman Islands Sentencing Guidelines: Sexual Offences (April 2020). 27 The justification for Category 2 Harm, it was submitted, includes the following: 28 • Prolonged detention/sustained incident – The complainant was under the 29 defendant’s control from Friday through to Monday morning. 30 • Forced or uninvited entry into the complainant’s home – The complainant 31 had not disclosed her new location to the defendant, who did not know where 32 she lived until he followed her home. 33 • Threat of violence - the defendant waylaid the complainant in the dark at her 34 apartment and pounced on her with a bladed item that he placed at her neck. 35 20250801- R v. Simpson (Orlando Roy). - Ind.108/2024. Coram: Palmer J. (Actg.). - Sentence Judgment.
The factors that were relied upon by the Crown to support Category A Culpability 1 are as follows: 2 • A significant degree of planning, including watching, following, and lying 3 in wait for the complainant. 4 • Prior violence against the victim from the July incident (for which the 5 defendant has been convicted of assaulting her). 6 Given this categorisation (2A), the starting point it was submitted, is 20 years' 7 imprisonment, with a sentencing range of from 15 to 24 years. 8 9
Threat to kill or cause serious harm, it was submitted, falls within Category 2 Harm 10 and Category A Culpability. To support a category 2 Harm, it was submitted that the 11 complainant experienced psychological distress and emotional trauma from the 12 incident (as she referred to in the VIR), and regarding Category A degree of 13 Culpability, it was submitted that the following conduct on the part of the defendant 14 contributed to this higher culpability classification: 15 • Use of a weapon – TM stated that a knife or bladed weapon was put to her 16 neck. 17 • A history of violence towards the complainant. 18 According to the Guidelines, a 2A categorisation for this offence yields a starting 19 point of 3 years and a range of 1 to 4 years’ imprisonment. 20 21
Assault Occasioning Actual Bodily Harm is categorised as lower harm and lower 22 culpability: 23 • The injuries were relatively minor in the context of the offence. 24 • The assault did not appear to be premeditated. 25 The Guidelines prescribe a starting point of a Community Order, with a range from 26 a fine to 12 months' custody. 27 28
The Crown highlights several aggravating features common to or associated with the 29 offences: 30 • The domestic context in which the violence occurred; 31 • The victim had to leave the home after the incident; 32 • There had been prior instances of abuse, according to the evidence of the 33 complainant. 34 35 20250801- R v. Simpson (Orlando Roy). - Ind.108/2024. Coram: Palmer J. (Actg.). - Sentence Judgment.
Regarding sentencing structure and totality, the Crown submits that the sentences 1 for Count 2 (rape) and Count 3 (threat to kill) may properly be ordered to run 2 concurrently, as they arose out of the same incident, but that they should run 3 consecutive to Count 1 (assault). It was however acknowledged that given the likely 4 sentence for Count 2, the court would not be faulted in ordering the counts to run 5 concurrently, especially in view of totality principle of sentencing. 6 7
It was contended that the primary mitigating feature for the defendant is the fact of 8 him having no convictions recorded against him and having proceeded to trial, is not 9 entitled to any discount for a plea of guilty. It was also acknowledged that he is 10 entitled to credit for time spent on remand from 28 March 2025 and time between 11 25 September 2024 and 28 March 2025, during which he was under curfew and fitted 12 with an electronic monitor. 13 14
The sentencing authorities relied upon by the Crown were instructive. In R v Jeffery 15 Alexander Barnes1 the defendant was convicted of a violent rape involving choking 16 and the use of a knife to cut off her clothes. The ordeal also had a psychological and 17 emotional impact on the complainant, who was left deeply traumatized. The 18 defendant was sentenced to life imprisonment for rape. The Court applied a Category 19 1A in the circumstances, which aside from the factors already mentioned, involved 20 significant planning and had a sustained impact on the victim and an offender with 21 prior rape convictions. There are similarities to the instant case, though the degree 22 of force involved and the degree of planning in Barnes appear to be greater. 23 24
In R v Teklu (Weldegabrial)2, the UK Court of Appeal upheld a sentence of 4 years 25 imprisonment for sexual assault. The appellant had positioned himself late at night 26 in an area frequented by lone women, engaged the complainant in conversation, 27 pursued her for some distance, manoeuvred her towards an alleyway and subjected 28 her to persistent sexual touching. The Court held that, in the context of this type of 29 offending, “significant planning” did not require sophisticated preparation; lying in 30 wait in a location suited to targeting lone young women returning home at night was 31 capable of amounting to a significant degree of planning. The Court further found 32 that the complainant was particularly vulnerable by reason of being a young woman 33 1 [Ind. No. 0087/2011-B] (delivered on September 23, 2013) 2 [2018] EWCA Crim 1477 20250801- R v. Simpson (Orlando Roy). - Ind.108/2024. Coram: Palmer J. (Actg.). - Sentence Judgment. alone at night, that the attack was sustained and frightening, and that the offender's 1 conduct during trial demonstrated a lack of remorse. The sentence was held not to 2 be manifestly excessive and the appeal was dismissed. 3 4
In R v Kapil Dogra3, the UK Court of Appeal considered whether an offender who 5 followed an 18-year-old woman from a railway station, selected an isolated location, 6 threatened her with a knife, forced her into woodland and subjected her to oral rape, 7 two assaults by penetration and compelled sexual activity had demonstrated a 8 “significant degree of planning” for the purposes of Category A culpability. The 9 Court held that, although the offender’s conduct involved pursuit, calculation and 10 some planning, it did not reach the elevated threshold of “significant planning” 11 required for Category A, observing that he had not identified the victim in advance, 12 conducted reconnaissance, armed himself beforehand or otherwise engaged in 13 substantial premeditation. The proper categorisation was therefore Category 2B 14 rather than Category 2A. Nevertheless, given the victim’s vulnerability, the 15 sustained and degrading nature of the attack, the threats of violence, the multiple 16 serious sexual offences committed during the incident, and the significant harm 17 caused, the Court upheld the sentence as not manifestly excessive. The offender had 18 been sentenced to an extended sentence of 15 years on the rape count, comprising 19 13 years’ imprisonment and a 2-year extension period, together with concurrent 20 sentences of 8 years’ imprisonment on each assault by penetration count and 4 years’ 21 imprisonment for causing the complainant to engage in sexual activity without 22 consent. The Court of Appeal noted that the appellant had shown little remorse or 23 empathy, as reflected in the pre-sentence report and his continued assertion that the 24 sexual activity was consensual. It highlights the lack of remorse and denial as 25 aggravating features, as is the case with Mr. Simpson. 26 27
In R v Travis Arlington Ebanks4 the defendant was convicted of two counts of rape. 28 The judgment explored the psychological manipulation and control exerted by the 29 accused, and the use of threats to force compliance, including threatening to tell 30 family and friends negative things about her if she did not meet with him. The 31 sentence was, after deductions, 13 ½ years on each count of rape. The case is 32 3 [2019] EWCA Crim 145 4 Indictment 4 of 2023 – delivered 11 April 2024 20250801- R v. Simpson (Orlando Roy). - Ind.108/2024. Coram: Palmer J. (Actg.). - Sentence Judgment. submitted as being useful due to similarities with the instant case in that there was 1 the use of threats, a past history of control and intimidation. 2 3 DEFENCE SUBMISSIONS 4 5
Given the seriousness of the offence of rape, it was acknowledged from the onset by 6 counsel that a custodial sentence is inevitable. However, the Court is urged to 7 exercise its discretion to impose a sentence at or near the lower end of the applicable 8 range, having regard to the absence of significant aggravating features and the 9 defendant’s compelling personal circumstances. 10 11
Counsel submits that the circumstances of these offences do not place this case 12 among the most egregious. Like the crown, it was submitted that this case falls within 13 Category 2 for Harm, in view of the absence of gratuitous violence and the lack of 14 any prolonged detention in the manner contemplated by the guidelines. Although the 15 incident occurred over the course of a weekend, and entry into the complainant’s 16 home was uninvited, it was contended that the harm, while serious, does not rise to 17 the highest level of psychological impact, particularly when the Court considers the 18 demeanour of the complainant during testimony and the nature of recorded post- 19 incident phone calls between the parties. 20 21
As for Culpability, there is divergence from the Crown’s position with a contention 22 that Category B is more appropriate. While the defendant did track TM to her new 23 residence and lay in wait, there was no evidence of sophisticated or elaborate 24 planning. The act, it was submitted, was largely opportunistic and spontaneous rather 25 than calculated. Consequently, the appropriate starting point, in counsel’s view, 26 should be 15 years’ imprisonment, with a range of 10 to 19 years under the relevant 27 Cayman Islands Sentencing Guidelines. 28 29
Counsel further submitted that a significant mitigating factor is the absence of 30 previous convictions in Jamaica or the Cayman Islands - the defendant now being 31 47 years old. Reference was made to several letters of reference from family, friends, 32 and his employer which portray a man of integrity, generosity, and strong work ethic. 33 This is reinforced by the SIR, which confirms that the Defendant is well regarded in 34 his community and has consistently demonstrated pro-social behaviour. 35 36 20250801- R v. Simpson (Orlando Roy). - Ind.108/2024. Coram: Palmer J. (Actg.). - Sentence Judgment.
The Defendant has not expressed remorse, and Counsel explains that this stems from 1 his continued belief in his innocence, rooted in the nature of the relationship he 2 shared with the complainant. He maintains that he had reason to believe the sexual 3 encounter was consensual, based on prior interactions and reconciliations between 4 them. His stance, counsel submitted, ought not to be treated as an aggravating factor. 5 6
Most striking is the defendant’s account of his personal background. Counsel 7 referred to the severe abuse he suffered at the hands of his father, and his deprivation 8 of formal education beyond the eighth grade, often to help his father with vehicle 9 repair. The harsh beatings, it was submitted, left both physical and emotional scars. 10 Despite this traumatic foundation, the defendant was able to migrate to the Cayman 11 Islands where he made a better life, established steady employment, and became a 12 source of financial and emotional support for his family. 13 14
The Court is urged to weigh these considerations heavily in its determination. 15 Counsel also invokes the principle of totality, particularly since the offence of 16 Assault Occasioning Actual Bodily Harm occurred on a separate occasion, and the 17 threats to kill were part of the incident involving the rape. While he concedes that 18 distinct sentencing may be required, he urges the Court to ensure that the total 19 sentence is proportionate and reflective of the overall criminality. 20 21
Ultimately, a sentence to the lowest end of the range of 10 years’ imprisonment, it 22 was submitted, appropriately balances the gravity of the offence with the defendant’s 23 personal circumstances, the absence of prior offending, and his demonstrated 24 potential for rehabilitation. 25 26 CHARACTER REFERENCES 27 28
The Court has received a detailed and emotional letter from the Defendant’s sister, 29 Mrs. Jodey-Ann Simpson-Holness, who writes both as a family member and as a 30 witness to the impact that this ordeal has had on the Defendant and their entire 31 family. Ms. Simpson-Holness pleads for mercy on her brother’s behalf. She 32 describes a man who is deeply devoted to his family and whose absence is 33 profoundly felt, particularly by her young children, who share a strong and 34 affectionate bond with their uncle. He was especially missed at the family’s recent 35 Good Friday gathering. She speaks to the defendant’s generosity, compassion, and 36 selflessness towards his family, which he continued even after being returned to 37 20250801- R v. Simpson (Orlando Roy). - Ind.108/2024. Coram: Palmer J. (Actg.). - Sentence Judgment. custody. She spoke of his assistance to her whilst she lived in Jamaica with her 1 college tuition and that he often sent financial support to others in need, even when 2 he had little for himself. She describes her brother’s present state of incarceration as 3 deeply troubling, both for him and for the family. He has since taken up smoking, a 4 habit he never previously had, to cope with stress and anxiety, and in her opinion, 5 his mental health has been visibly affected. She acknowledges the weight of the 6 Court’s task but implored it to consider the totality of the defendant’s life and the 7 man that he is for his family. The letter concludes with a heartfelt appeal for 8 compassion and mercy, asking the Court to consider not only the seriousness of the 9 offence but also the defendant’s potential for healing, rehabilitation, and eventual 10 reintegration into society. 11 12
A letter expressing similar sentiments was received also from the Defendant’s 13 mother. 14 15
The Defendant’s other sister, Ms. Staceyann Hall, also provided a letter to the Court. 16 She corroborated accounts of his childhood abuse at the hands of his father. 17 Nevertheless, she stated that he chose the honest, though difficult path, working on 18 construction sites from the age of 16 and eventually migrating to the Cayman Islands, 19 where he sought a better life. She asserts that despite his painful past, he remained 20 generous, supportive of family and friends, and free from crime or drug use. With 21 respect to the offence, Ms. Hall expressed confidence that Mr. Simpson did not 22 intend harm, suggesting that what occurred may have stemmed from a tragic 23 misunderstanding between former intimate partners. 24 25
Mr. Tyrone Francis, a friend of over twenty-five years, described the defendant as a 26 man of integrity, humility, and resilience, deeply committed to personal growth and 27 to making a positive contribution to society. He highlighted the defendant’s work 28 ethic, especially in the field of construction and home renovation, and credits him 29 with meaningful contributions to the development of Grand Cayman, both before 30 and after Hurricane Ivan. He expressed confidence that the defendant, if given the 31 opportunity, will continue to be a positive influence in the Cayman Islands, and he 32 pledged his personal support to him. 33 34 35 36 37 20250801- R v. Simpson (Orlando Roy). - Ind.108/2024. Coram: Palmer J. (Actg.). - Sentence Judgment.
The Court also received a reference from the Defendant’s long-standing employer, 1 who employed him with his companies during two periods: from 2005 to 2007 and 2 again from 2018 until the present. He describes Mr. Simpson as amicable, honest, 3 and hardworking, noting that he was well-regarded by supervisors and colleagues 4 alike, and consistently fulfilled his duties. Mr. Langlois expresses his shock and 5 dismay upon learning of the charges, which he states are entirely out of character for 6 the man he and his staff came to know. 7 8 CONCLUSION 9 10
The Crown advocates for a sentence towards the upper end of the Category 2A range, 11 highlighting aggravating features such as the complainant’s psychological harm, use 12 of a weapon, and sustained control over the victim. In contrast, the defence argues 13 for a Category 2B classification, downplaying the planning and impact, and 14 proposing a sentence at the lowest end of the spectrum (10 years). Both sides accept 15 that the custody threshold has been surpassed, and a period of confinement is 16 inevitable. The key divergence lies in how the offence of rape, given the severity of 17 the sentence that it carries, should be categorised under the guidelines and how much 18 weight should be given to the defendant’s early personal history, remorsefulness (or 19 the apparent lack of it), and the circumstances of the incident, in determining the 20 final sentence. 21 22
The facts established at trial disclose that he located the complainant, his former 23 partner, after she had removed herself from his presence and gone to some lengths 24 to avoid him. He lay in wait for her and, upon confronting her at her residence, he 25 compelled her at knife or blade-point to return with him to her apartment. There, in 26 a state of fear, she submitted to sexual intercourse, which the Court has found was 27 not consensual. 28 29
There is no dispute that these offences all exceed the custody threshold. As Count 2 30 that charges the Defendant with rape, which invariably attracts an immediate and 31 lengthier custodial sentence (See R v Jeffery Alexander Barnes), I will treat with 32 the appropriate sentence for this count first. Reference is made to the Cayman 33 Islands Sentencing Guidelines – Sexual Offences (April 2020). Having considered 34 all the circumstances of the rape offence, the relevant guidelines and authorities, I 35 classify the offence as falling within Category 2B, reasoned as follows: 36 20250801- R v. Simpson (Orlando Roy). - Ind.108/2024. Coram: Palmer J. (Actg.). - Sentence Judgment. • Harm: Category 2 harm, due to the psychological impact on the 1 complainant, as shown in the VIR. Reference is made to trauma, fear, 2 anxiety, and residual hypervigilance she has been left experiencing. She 3 expressed a need to constantly look over her shoulder, insomnia and anxiety 4 attacks. 5 • Culpability: Category B culpability, due to the absence of advanced 6 planning, there was no prolonged violence, and the degree of force was 7 moderate. The incident fortunately did not involve a group and though their 8 relationship was tumultuous there is no evidence to support a contention of 9 repeated offending. It is important to note, however, that the use of a weapon 10 when the August incident began, together with the controlling conduct, 11 while aggravating, were not sustained at the highest levels of force seen in 12 Category A cases. 13 14 AGGRAVATING FACTORS 15 16
While the classification places the offence in Category 2B, the following aggravating 17 factors were among those considered: 18 • Controlling and coercive behaviour: This was a pattern, not a one-time 19 occurrence. The complainant had previously felt compelled to relocate for 20 her safety. He found her address by covert means and used his presence, 21 physical strength, and prior relationship dynamic to assert dominance. 22 • Psychological harm: The complainant continues to suffer significant 23 trauma, including anxiety, sleep disturbance, and fear for her life. 24 • Use of a weapon and threats: use of a knife to coerce compliance and issuing 25 threats which led the complainant to believe that resistance would result in 26 serious harm. 27 • Failure to acknowledge the lack of consent: His belief in the complainant’s 28 consent was, in the Court’s view, not only mistaken but wholly unreasonable 29 in the circumstances. The way in which he came to be at her residence, by 30 lying in wait and forcing his way into her residence, renders any such belief 31 devoid of credibility. 32 33 34 35 20250801- R v. Simpson (Orlando Roy). - Ind.108/2024. Coram: Palmer J. (Actg.). - Sentence Judgment. MITIGATING FACTORS 1 2
Balanced against those aggravating features the following factors are among the 3 factors considered in his favour: 4 • No prior convictions: He has no convictions neither in the Cayman Islands 5 nor in Jamaica, where he spent is formative years. 6 • Severely abusive childhood: He suffered repeated physical abuse by his 7 father from a young age. This trauma seems to have had long-term impacts 8 on his emotional development and ability to build healthy relationships, as 9 confirmed by the SIR and reference letters. 10 • General good character and work ethic: He maintained lawful employment 11 as a mason for nearly 30 years and have consistently supported his family 12 and others financially and emotionally. Several persons, including his 13 mother and sisters, provided references in relation to the Defendant’s 14 otherwise upstanding behaviour. 15 • Strong prospects of rehabilitation: The Social Inquiry Report (SIR) assessed 16 the Defendant’s overall risk of reoffending as medium but noted low to very 17 low risk in key criminogenic areas such as companions, criminal history, 18 and substance abuse. The Defendant is therefore a suitable candidate for 19 targeted rehabilitation programmes. 20 • Degree of force not prolonged or excessive: Unlike the circumstances in R 21 v Barnes, this was not a brutal or repeated attack. There was no gratuitous 22 violence or prolonged physical restraint beyond what was necessary for the 23 Defendant to assert coercive dominance in that moment. 24 25 SENTENCING FOR RAPE (COUNT 2) 26
Dealing first with the most severe offence of Rape at Count 2 of the indictment, for 27 a Category 2B rape offence under the Cayman Islands Sentencing Guidelines, the 28 starting point is 15 years, with a range of 10 to 19 years. While I agree that 29 aggravating factors are present, I find that the absence of advanced planning, coupled 30 with his background and positive social functioning, make a sentence within 31 Category 2B proportionate I all the circumstances. 32 33 34 20250801- R v. Simpson (Orlando Roy). - Ind.108/2024. Coram: Palmer J. (Actg.). - Sentence Judgment.
Applying the starting point of 15 years, 5 years is added for the aggravating features, 1 for a total of 20 years, and 7 years deducted for those factors that weigh in his favour, 2 the sentence of this court on Count 2 that charges the Defendant with rape is 13 3 years’ imprisonment. 4 5 SENTENCE FOR ASSAULT (COUNT 1) 6
Count 1 - Assault Occasioning Actual Bodily Harm (AOBH) - is categorised as 7 lower harm and lower Culpability: 8 • The injuries were relatively minor in the context of the offence. 9 • The assault did not appear to be premeditated. 10 The Guidelines prescribe a starting point of a community order, with a range from 11 a fine to 12 months' custody. 12 13
The following aggravating features are common to or associated with the offences: 14 • The domestic context in which the violence occurred; 15 • The victim had to leave the home after the incident; 16 • There had been prior instances of abuse, according to the evidence of the 17 complainant. 18 The sentence imposed for Count 1 that charges assault occasioning actual bodily 19 harm is 9 months’ imprisonment. 20 21 SENTENCE FOR THREAT TO KILL OR CAUSE SERIOUS HARM 22
Threat to kill or cause serious harm, it was submitted, falls within Category 2 Harm 23 and Category A Culpability. To support a category 2 Harm, it was submitted that the 24 complainant experienced psychological distress and emotional trauma from the 25 incident (as she referred to in the VIR). For category A culpability, it was submitted 26 that the following conduct on the part of the Defendant contributed: 27 • Use of a weapon – TM stated that a knife or bladed weapon was put to her 28 neck. 29 • A history of violence towards the complainant, supporting the higher 30 culpability classification. 31 According to the Guidelines, a 2A categorisation for this offence yields a starting 32 point of 3 years and a range of between 1 and 4 years’ imprisonment. For count 3 33 that charges the Defendant with the offence of Threat to kill or cause serious harm, 34 the sentence is 3 years’ imprisonment. 35 20250801- R v. Simpson (Orlando Roy). - Ind.108/2024. Coram: Palmer J. (Actg.). - Sentence Judgment. CONSECUTIVE OR CONCURRENT SENTENCE 1 2
I have considered whether a consecutive sentence is warranted. While I acknowledge 3 that Count 1 occurred at a different time than count 1, when consideration is given 4 to the principle of totality, the maximum of 13 years is considered a suitable period 5 of confinement. All sentences are therefore made to run concurrently. 6 7 CREDIT FOR TIME SPENT AND UNDER CURFEW OR ELECTRONIC MONITORING 8 9
Regarding the time served the Defendant will receive credit for time spent in custody 10 from March 28, 2025 to the date of sentencing. Time during which he was 11 electronically monitored and under curfew, from 25 September 2024 to 28 March 12 2025 will also be taken into account and credited administratively by the prison 13 authorities. 14 15 APPLICATION FOR A SEXUAL HARM PREVENTION ORDER (SHPO) 16 17
The crown has sought leave to apply for a Sexual Harm Prevention Order, and leave 18 has been granted for them to do so within the next two weeks. If applied for, the 19 recommendations made relating to any post-sentence restrictions can be considered. 20 21 ORDERS 22 23
Based therefore on the foregoing, and for the avoidance of doubt, the following are 24 the orders of this court: 25 (i) Sentence on Count 1: Assault Occasioning Actual Bodily Harm – 9 26 months’ imprisonment. 27 (ii) Sentence on Count 2: Rape – 13 years’ imprisonment. 28 (iii) Sentence on Count 3: Threat to kill or cause serious harm – 3 years’ 29 imprisonment. 30 (iv) Counts 1 – 3 are to run concurrently. 31 (v) The Defendant is to receive credit for time: 32 (a) spent in custody from 28 March 2025 to today’s date. 33 (b) under electronic monitoring and curfew from 25 September 2024 34 and 28 March 2025. 35 20250801- R v. Simpson (Orlando Roy). - Ind.108/2024. Coram: Palmer J. (Actg.). - Sentence Judgment. (vi) The Prosecution is granted leave to make an application in relation to a 1 Sexual Harm Prevention Order, within two weeks of the delivery of this 2 decision. 3 4 5 Dated this the 1st August 2025, 6 7 8 JUSTICE DALE PALMER 9 ACTING JUDGE OF THE GRANT COURT 10 11 12