Jailed For Driving, Spared For Ganja: Two Months For Repeat Traffic Offender

By Alric Lindsay

Damion Ainsley Livingston, a man who has several previous traffic convictions and a record of drug offending, appeared in the Summary Court today, July 20, 2026 to face charges of Ganja possession and consumption, driving without insurance, using a vehicle without a certificate of roadworthiness, using a vehicle with an expired license and driving whist not being qualified.  Livingston was sentenced to an immediate two months in prison for persistent unlicensed and uninsured driving, while a combined 14 months and 14 days’ imprisonment for possessing and supplying Ganja was suspended for two years.   

The first set of cases related to an  incident on January 20, 2023.  The court heard that, at around 7am, officers from the traffic management unit, patrolling in a police vehicle, were exiting Agnes Way  to travel along Crewe Road when they observed a white Honda Accord. A check of the vehicle’s registration showed its papers were out of date, and officers activated emergency lights and sirens to stop the driver, who was identified as Livingston.

Livingston failed to stop, and a chase followed; after evasive manoeuvres he was found in a different vehicle apparently attempting to leave the area. He was found to be carrying backpack containing a large quantity of vegetable matter resembling Ganja, packaged in portions in sealed packets.

Livingston  first appeared before the court on this matter on August 27, 2024. In  October 2024 he pleaded not guilty to possession with intent to supply but guilty to simple possession, and he also pleaded guilty to a charge of consumption.

In November, Crown Counsel from the Office of the Director of Public Prosecutions indicated it would proceed with the possession-with-intent charge. Following a number of adjourned trial dates, on January 27, 2026 a basis of plea was accepted on the footing that the supply was social supply, and Livingston pled guilty. He also pled guilty to the associated traffic offences, and an interim driving disqualification was ordered at that stage. Because of his record for drug offences, it was noted in court that the maximum penalty available was a fine of $10,000 or ten years’ imprisonment.

After analysing the sentencing guidelines, the Chief Magistrate said that the starting point would be 18 months. Mitigating factors included the length of time since his last offence, steady employment, family commitments and his general background.

The Chief Magistrate deducted five months for personal mitigation, but limited any further discount to one-tenth given that his guilty plea “came very late in the day”. The resulting sentence was 11 months’ imprisonment for possession with intent to supply and 14 days for consumption.

On the traffic matters, the Chief Magistrate  said Livingston faced a custodial sentence and a fine, and stated bluntly that “persons who have never been qualified to drive in the Cayman Islands must not drive in the Cayman Islands.”

Livingston’s record showed more than 25 previous traffic offences, five of them for driving without authorisation including one of driving while disqualified, and six for driving without insurance, which the judge said showed “a blatant disregard for the laws of our roads.”

Noting that Livingston had served custody for such matters before without deterrent effect, the Chief Magistrate  said the court took a firm “three strikes” approach before matters became custodial.

In the circumstances, the Chief Magistrate sentenced Livingston for the traffic offences as follows:

**5 weeks for driving without insurance

** 7 days for an offence concerning a certificate of roadworthiness

** 7  weeks for driving with an expired vehicle licence

** 2  months for driving while never qualified

The Chief Magistrate said that the traffic sentences to run concurrently with each other but separately from the drug sentences.

In relation to the second set of offences, this relates to incidents that occurred on April 19, 2024. 

Livingston first appeared on May 20, 2025 and pled not guilty to all matters on July 15 2025. A trial date was fixed, but on  November 12 he pled guilty to simple possession, which DPP Crown Counsel indicated it would accept.

Again his plea came late, on the morning of trial. The Chief Magistrate accepted that both harm and culpability were low and that the quantity involved fell within category 4, sentencing him to three months’ imprisonment.

Before passing sentence, the Chief Magistrate said she had considered whether a community-based sentence with rehabilitation might be appropriate but expressed doubt, saying “I’m not sure about rehabilitation… nothing has indicated to me that he’s serious about rehabilitation,” adding that his traffic record did not assist him and that he had been warned before.

The total sentence for the drug matters across both cases, 11 months and 14 days plus three months, running consecutively, came to 14 months and 14 days, which was suspended for two years.   The Chief Magistrate warned Livingston that if he commits any further offence during that two-year period the full 14-month-and-14-day term will be activated.

The traffic offences, described by the Chief Magistrate as “a different kettle of fish”, resulted in a total of 2 months’ imprisonment to be served immediately, alongside a 12-month driving disqualification from January 27, 2026.

The drugs were ordered forfeited and destroyed, and Livingston was told he had a right to appeal.