
A convicted British criminal who duped more than 20 Kiwis into giving him $337,700 after posing as a police courier says he is now disgusted and embarrassed by his actions.
Jack Dylan Hennessy, who is in prison for scamming 21 mostly elderly victims in 2024, today told a panel of Parole Board members how truly sorry he was.
“I’m disgusted by my actions. I’m disgusted, embarrassed and feel stupid,” he said.
In a letter he read at the hearing, he said he wanted to become the best man he could, rather than be remembered for what he had done if he were to die tomorrow.
But the panel was not convinced of his sincerity, because he refused to co-operate with police and tell them who was behind the scam ring he was part of.
NZME reported last year Hennessy claimed he was blackmailed into his actions after losing a luxury $200,000 Swiss watch loaned to him by dangerous British criminals.

The panel declined his release, saying the board needed to be satisfied he had completed rehabilitation programmes that ensured communities he was released back into, in New Zealand and in Britain, were safe from any further offending.
The 26-year-old, who was facing deportation upon his release, was jailed in the Auckland District Court last November for three years and three months for the offending, described by Judge Kevin Glubb as “reprehensible”, premeditated and “carried out with almost military precision”.
‘Intense shame’
After landing in Auckland on June 9, 2024, Hennessy rented an apartment on Hobson St, then proceeded to steal $337,700 over the next 14 days from 21 people aged from 59 to 92.
His victims thought they were assisting an elaborate law enforcement investigation.
They were called by scammers posing as police officers. They were then convinced to withdraw large sums of money from their bank accounts in the belief they were assisting undercover detectives in a sting operation targeting counterfeit banknotes.
Hennessy used taxis to visit the victims’ homes to collect the cash, posing as a plain-clothed police courier. He used prearranged code words including “aroha”, “totara”, “treetop” and “Timbuktu” to convince his victims he was a genuine state operative.
They believed that after handing the money to Hennessy, it would be whisked to investigators, checked for fake notes, then redeposited into their accounts.
In reality, the money was either pocketed by Hennessy or sent to his bosses overseas.
Hennessy told Parole Board panel convenor Neville Trendle that he was told to contact a person in Auckland, who took a cut from the money he handed over, and who then transferred the rest as cryptocurrency.
Several victims spoke of their intense shame after realising they’d been duped, the devastating financial effects on their retirement plans, and feelings of fear and violation that the scammers knew their addresses and had personally visited their homes.
Hennessy was caught on June 24 on his way to pick up $20,000 from an 83-year-old victim who had already handed over $16,000.
After being spotted in a taxi in central Auckland, he led police on a brief foot chase before being arrested.
He later admitted 27 charges, including obtaining by deception and one of escaping custody.
Panel not convinced
The hearing panel said that banks had so far covered a lot of the losses incurred, but $28,000 remained outstanding, which Hennessy said he intended to repay.
How he might do that was challenged by panel member Sharon Gemmell, who stressed that the people targeted by Hennessy belonged to the most vulnerable sector of the community.
Hennessy said he planned to get a job once back in Britain and arrange to have deductions made, possibly through the Ministry of Justice, but he was unsure who to approach and how to go about it.
However, Gemmell was not convinced he had tried hard enough to find a way by which he might make good on his promise. She said he was a “clever young person” who had come to the country and straight away began scamming people, yet he was not able to figure out how to pay the money back.
“I’m very reluctant to see you sail off to the UK and not make any arrangement to pay that back.”
Hennessy has previously served time in a British prison for his role in a smash-and-grab gang targeting mobile phone stores.
He claimed he only agreed to board the flight to New Zealand and pick up packages stuffed with cash after a British crime syndicate threatened to harm his mother and brother.
Hennessy told panel member Olivia Brittain, who asked why he had not co-operated with the police in helping to identify others involved, that giving up names would put the rest of his life in jeopardy.
“They’re not people to be messed with,” he said.
Brittain said that he was denying his elderly victims. Hennessy said that at the time he was only thinking of himself, but the consequences of what he had done crept up “day by day”.
Trendle said it remained a mystery how Hennessy had become involved. Trendle said that hearing the Briton talk about the restorative justice process he had taken part in, and how sorry he was, did not sit well with the convenor when the prisoner refused to co-operate with the police.
“It means that remorse and indications of repayment are meaningless,” Trendle said.
Hennessy would now have to complete rehabilitation programmes and devise a safety plan before being considered again for parole in January.