Court Hears Sentencing Arguments For Man Who Took Woman At Knife Point Outside Her Home & Raped Her. He Faces Up To 24 Years In Prison.

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By Alric Lindsay

46-year-old Orlando Roy Simpson, who was previously found guilty of rape, threats to kill and assault causing bodily harm after trial, appeared via video link in the Grand Court on July 4, 2025, to hear sentencing arguments. Reportedly, the crimes were committed against a woman with whom Simpson was said to have previously been in a relationship. Following the breakup, Simpson lay waited outside her home after discovering where she lived, held her at knife point and raped her. Based on the sentencing submissions from Orrett Brown, Crown Counsel for the Office of the Director of Public Prosecutions, he faces up to 24 years in prison. However, this may be less if the Honourable Acting Justice Palmer accepts the arguments from attorney Crister Brady, Simpson’s defence counsel.

Sentencing arguments for rape

Setting out the prosecution’s sentencing argument against Simpson, DPP Crown Counsel Brown said that rape is always a serious crime and “calls for an immediate custodial sentence.”

Citing a previous rape case, DPP Crown Counsel Brown explained that a custodial sentence is necessary to:

**Mark the gravity of the offence

**Emphasise public disapproval

**Serve as a warning to others

**Punish the offender

**Protect the woman

Turning to the Cayman Islands Sentencing Guidelines on sexual offences dated April 2020, DPP Crown Counsel Brown suggested that the rape fell within Category 2A. This was on the basis that Simpson detained the woman for a prolonged period, and there was a significant degree of planning. This would result in a starting point of 20 years imprisonment, with a possible sentencing range from 15 to 24 years.

DPP Crown Counsel Brown supported his argument, explaining that the woman did not tell him where she lived and, instead, Simpson watched, followed and lay in wait for the woman. Simpson surprised the woman, held her at knife point, telling her not to raise any alarm and took her into the apartment. As such, Simpson’s entry into the apartment was uninvited, and he held the woman from Friday through to Monday morning, at which time she reported the rape to the police.

Simpson’s lawyer, Crister Brady, disagreed with the prosecution’s suggested term of imprisonment, saying that it should be categorised under Category 2B of the Sentencing Guidelines on sexual offences. If the Honourable Acting Justice Palmer agrees, this would reduce the starting point for the rape to 15 years imprisonment, with a sentencing range of 10 to 19 years.

Defence Counsel Brady said this view was taken because the rape could not be described as one involving a significant degree of planning, and Simpson’s waiting around for the woman by her residence was an “unsophisticated” act.

Sentencing arguments for threats to kill

Looking at the proposal for the sentence for threats to kill, DPP Crown Counsel Brown said that, under the Cayman Islands Sentencing Guidelines for Public Order Offences, this offence should be categorised as Category 2A. This would result in a starting point of 3 years’ imprisonment, with a possible sentencing range of 1 to 4 years’ imprisonment.

DPP Crown Counsel Brown supported his argument by saying that the woman suffered some distress and psychological harm. In addition, Simpson used a visible weapon, a knife.

DPP Crown Counsel Brown added that there were aggravating features that could increase the sentence. These were as follows:

**Location: the offence occurred at the woman’s home, where she should feel safe.

**Time: the incident took place at night, when the woman just returned home and was “pounced upon” in the cover of darkness as she walked to her apartment.

**Use of a knife to frighten the woman

Sentencing arguments for assault causing bodily harm

Finally, for assault causing bodily harm, which reportedly occurred before the rape when Simpson was living with the woman. Reportedly, it was this assault that led the woman to leave the home.

Commenting on the proposed sentence for assault, DPP Crown Counsel Brown said that under the Sentencing Guidelines for Violent Offences, this offence should be categorised as one of lower culpability and harm. This would result in a starting point of a community order, with a possible sentencing range of a fine to 12 months’ custody.

DPP Crown Counsel Brown supported his argument by pointing out that the assault was less serious in the context of the offence and there was a lack of premeditation.

Proposed sentence reductions

Since the Honourable Acting Justice Palmer is entitled to consider reductions in the sentences for the above crimes, DPP Crown Counsel Brown suggested that, since Simpson was convicted after trial, he should not be eligible for the usual one-third reduction in prison sentence for an early guilty plea.

However, DPP Crown Counsel Brown noted that Simpson should receive credit for time already spent in custody since March 2025, time spent on curfew and wearing an electronic monitor while on bail.

DPP Crown Counsel Brown added that the Honourable Acting Justice Palmer was also entitled to consider running all sentences concurrently or having the rape run as one sentence and one or more of the other sentences run consecutive to the rape.

What happens next

The Honourable Acting Justice Palmer will review the submissions from prosecution and defence counsels, along with any character references and reports submitted. He is expected to deliver the final sentence judgment on July 25, 2025.