Judith Douglas, pictured in August 2023, is led away in handcuffs by a prison officer after pleading guilty to obtaining property by deception. - Photo: Andrel Harris.

Prosecutors have called for a tough sentence for a serial con-woman who stole more than $50,000 from a string of victims in a rental scam that left them homeless and scrambling for cash.

Judith Douglas admitted the con and claimed to have squandered the proceeds in Cayman’s illegal ‘gambling dens’.

The scheme involved using a single property to get a rental deposit and first month’s payment from 32 different people.

During a sentencing hearing, Wednesday, she submitted a letter of apology for her crimes and insisted she was seeking help for gambling addiction.

At an earlier hearing, Douglas had entered mixed pleas (the majority of which were guilty) to 36 counts of obtaining property by deception.

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The charges stemmed from a scam initiated by Douglas between December 2022 and March 2023 – some eight months after she was released from prison having been sentenced to five years for conning a man out of $1.9million with a promise of Caymanian citizenship.

When entering her guilty pleas last year, Douglas told the court, through her attorney Jonathon Hughes, that she was sucked into a spiraling plan in which she found herself “taking from Peter to pay Paul”.

At Wednesday’s hearing, prosecutor Nimesh Jani, told Justice Cheryll Richards the evidence his office has seen suggests Douglas is only concerned about herself.

“From what we have seen, it seems that Douglas was more interested in taking from Peter rather than the paying Paul part,” said Jani.

During his submissions, Jani stated that, although Douglas was unemployed upon her release from prison and had no savings, she was able to spend $11,264.89 on online shopping sites like Amazon and Health Super Food.

“Of the remaining $40,670.31, we have no evidence of how those monies were spent. What we do know is that it was spent by Douglas doing what she wanted to do, and not spent on the paying Paul part,” said Jani.

The prosecutor said she had targeted low income earners on work permits, many of whom could not afford to lose $1,000, for the scam, in which she took rental deposits and a month’s rent from multiple people for the same property.

He added, “Several of her victims were unable to recover from the loss and had to leave the island.”

Douglas used this rental property on her family-owned plot of land to dupe unsuspecting victims into paying one month’s rent and a deposit. – Photo: Andrel Harris

A history of scamming

Pointing to Douglas’s past offending, Jani reminded the court of her 10 previous convictions “most of which were for dishonesty offences and obtaining by deception”.

Douglas was jailed for two-and-a-half years for a scam during which she promised her victims they would receive Cayman permanent residency for approximately $2,500 each. Through that scheme, she stole $104,500.

While behind bars for that crime, she continued her offending, this time her sole victim was conned out of $1.9 million with a promise of obtaining Caymanian status and a passport.

According to Jani, an appropriate sentence would be a term of between six and eight years in jail.

When responding to the prosecution’s case against Douglas, her attorney called on the courts to show compassion for a woman who had a pernicious addiction, rooted in child abuse and neglect.

Childhood trauma led to a life of gambling

According to Hughes, Douglas’s traumatic past caused her to develop an unhealthy understanding of human relationships and interactions, which in turn led to her developing an addiction.

“She was chained and beaten as a child, and made to feel as if she was worthless,” said Hughes. “This was in addition to repeated sexual abuse.”

He added that the perpetrator of the abuse had “introduced her to gambling at the age of 14, and it is in gambling that she found a misplaced sense of comfort and joy.”

During his submissions, he read aloud from a letter Douglas had penned to the court apologising for her actions and pleading for help with a chronic gambling addiction.
“I write this letter with deep remorse regarding the crimes I committed and the impact they had on the victims,” she wrote.
While in prison, she said she had sought help from a psychiatrist to better understand the reasons for her repeat offending.
Douglas said she had been consumed with guilt over her actions and was seeking help for her addiction issues.
Speaking on her behalf, Hughes said she had gambled away the vast majority of the $52,000 she had gained from the enterprise.
He said she had lost the money from the first victim – a sum of around $1,000 – and then gambled funds from the next in an effort to win back what she had lost.
Judith Douglas is led away in handcuffs on Friday, 25 Aug., after admitting to stealing nearly $70,000.
He acknowledged this was a “foolish plan that didn’t work”, adding, “she got deeper and deeper into a hole trying to pay back individuals she had taken money from.”
But he insisted she was desperately scrambling behind the scenes in an effort to pay people back.
He said there was no paper trail to demonstrate how she had lost around $40,000 in this fashion because gambling is illegal in Cayman.
“It happens in cash in back alleys and local gambling dens,” he said, citing evidence that Douglas had logged into gambling sites 11,000 times during the 85-day period spanning the offences as corroborating evidence of an addiction issue.
Douglas was remanded into custody until Wednesday, 28 Feb. at which time she is expected to be sentenced.