How Pat Sheedy used fraud to fund his gambling addiction: ‘I was convincing. I could make you feel sorry for me’

Pat Sheedy was released from prison last August. Now, less than six months later, he is publishing his memoir, A Hundred to One: 100 Convictions, 1 Million Euro – The Devastating True Story of a Compulsive Gambler. Sheedy, who meets me in a cafe in Dublin’s Smithfield, wanted to call it “From the Bookies to the Big House”. These days he’s thoughtful, contrite and ashamed of his former behaviour, but he has a long history of fraud in the service of a gambling addiction. He estimates that he has squandered at least €1 million on gambling.

Sheedy discovered writing while in Portlaoise Prison, thanks to a teacher called Shauna Gilligan. I’ve visited the school at Portlaoise twice. The prison school is a counter-intuitively warm and kind place. Gilligan and her colleagues believe there’s more to people than their crimes and that prison should, ultimately, be about rehabilitation.

Last year I met and interviewed several prisoners, as well as an ex-prisoner, Sheedy’s friend Paul O’Rourke, to whom the book is dedicated. O’Rourke was a gentle recovering drug addict and an advocate of prison education. He died suddenly of heart failure last December. “Paul was sensitive and passionate about education,” says Sheedy. “I was devastated. He was turning it around.”

Sheedy, a repeat offender, is also hoping to turn things around. He first gambled at the age of 12 and pulled off his first scam on the same day. His father sent him to the bookies, where he put only 10 of the 30 pence he was given on the docket, figuring he could alter the one to a three before giving it back to his father. As a child who had been bullied, the bookies seemed like a colourful, welcoming place. “I more or less decided there and then, ‘This is for me.’”

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I wasn’t a master criminal ... A lot of the time I’d use my own name. I’d use my own mobile number. Maybe I wanted to get caught

The list of crimes in the book can be exhausting because Sheedy is blisteringly honest. He hides nothing. In his early 20s he stole a blank cheque from a neighbour; he set up bank accounts in different banks and used their overdraft facilities to gamble; he was hired to raise money for a housing body but pocketed a cut of each pledge. How could he do those things? “The logic was ‘What I’ve stolen from you, I am going to pay back.’ I always thought, okay, I might have four or five losses for every one win, but then I’ll have that one big win.”

In the aforementioned cases he was, respectively, given probation, sentenced to 240 hours of community service and given a suspended sentence of 15 months. In the latter case, he was terrified and sought treatment. After this he managed to stay gambling-free for more than a decade, attending Gamblers Anonymous meetings every week. He got a job in ad sales with a magazine in Dublin which developed into a senior marketing and public relations role. He realised much later that a desire for status was part of the problem. It was one of the things that drove him to gamble. “I had the five-series BMW. I wore the fancy suits. That all fitted in with the status that I wanted. I wanted people to look at me and say, ‘Wow, he’s got it all.’”

One day, after 13 years, he walked into a bookies, placed a bet and his life fell apart. He lost all of his savings and began committing fraud once more to fund his gambling. This time his spree came to an end when he procured a large bank overdraft on false pretences, gambled it away and was found out. Does he feel the people he defrauded were foolish? “I was extremely convincing,” he says. “I had no doubt that, if I set my mind to it, I could concoct a scheme or story that would make you feel sorry for me. That doesn’t make you a fool. It just makes me a manipulative person.”

That was his second wake-up call. He went into residential treatment and subsequently received a four-year suspended sentence. He, again, managed to stay gambling-free for many years, but, as the pressures of life began to mount – an upsetting break-up, the death of his father (he writes movingly about these things in the book) – he started gambling again. Whereas the old-fashioned bookies had limited opening hours, the online operators were always open. He recalls sitting on his bed at three in the morning with an iPad, a laptop and a smartphone open in front of him. “I was gambling on Indian basketball; I was gambling on some croquet match in Thailand; and virtual cartoon racing, virtually generated racing, just to have a bet on.”

How did he fund this? He told a landscape gardening friend he could get him cheap equipment then gambled the money he gave him (he repaid this but served a short sentence). He sold people Rugby World Cup tickets that didn’t exist. He conned an electronics company into giving him expensive phones by saying he was with a TV documentary team. And those are just some of the schemes he orchestrated. “They were harebrained,” he says. “I wasn’t a master criminal ... A lot of the time I’d use my own name. I’d use my own mobile number. Maybe I wanted to get caught. I was like a drug addict looking for a quick fix for my next bet.”

Over the years, Sheedy has racked up 97 convictions, not all for fraud, he says, “but if 20 of those offences were for parking, I can guarantee they were all within 100 metres of a bookie.” In October 2020, he was sent to jail for what would ultimately be two years and 10 months. The bulk of this time was spent in Portlaoise. It was there, he says, that he properly reckoned with the consequences of his actions, with the help of a prison counsellor. “[She] made me look at the effect my behaviour had on other people, about how I made my parents feel, about how I made my friends feel, about how the people I had stolen from felt.”

He also began to write, with the encouragement of Shauna Gilligan. In 2021 and 2022, Sheedy won the Writing in Prison award at Listowel Writers’ Festival for his short story writing. He also began writing his memoir. “It was like a cleansing. I just decided that I was going to write the truth.”

[ ‘Gambling is by and large a very secretive addiction’ ]

Gilligan was very kind to him. Being a prisoner is dehumanising, he says. “You’re getting roared at by other prisoners. You’re getting abuse from some prison officers. You come to expect abuse. Then, when you go to school, it’s so refreshing to sit and be treated like a real human being. Prison educators do an amazing job in volatile circumstances. They’re incredible people. And they’re not helped or resourced enough.”

Sheedy was in prison during the Covid-19 lockdowns and he counts 34 days where he didn’t leave his cell once. “Because you’re on 24/7 lockdown, nobody’s getting out to landings or yards,” he says. “There can be no drug deals. Very shortly into the Covid lockdowns, I’d be lying in bed at one o’clock in the morning and all you hear are screams, addicts in withdrawal. It was heartbreaking.”

Was prison frightening? “I was on a landing with pretty hairy people but I never had a problem in prison with anybody and that’s probably testament to my ability to adapt and to fit in,” he says. “To a degree, it was a scam of a different kind, because I had to put on a mask and pretend I was somebody else. Talk the talk.”

For him the worst part of the experience was worrying about his mother, who had been diagnosed with Alzheimer’s. He had two six-minute calls home each day. “There were times where she wouldn’t pick up the phone and my head would just melt. I’d be getting the chaplain to ring home and see was everything okay. At the time of her life where she needed me most, I wasn’t there. That really hurt.”

When I took a break [from gambling], I’d be bombarded with offers. You can’t watch any kind of sporting event without being bombarded with ads

He lives with her now and he has good relationships with some, but not all, of his family. He stresses a few times that not all gambling addicts end up committing crimes (“Not all gambling addicts have a mind like mine”) and he hopes to repay the faith that his counsellors, teachers, family and friends have put in him. He’s doing the work, going to the GA meetings and trying to be better. He’s currently working with an organisation called Spéire Nua, which helps prisoners find employment, and another called the Bedford Row Family Project, which works with the families of prisoners. He’s planning to teach creative writing in prisons.

He is also hopeful that the upcoming Gambling Regulation Bill will force the industry to take stock of the havoc caused by problem gambling. He recalls big operators inducing him with free trips and tickets to events at the height of his addiction. “When I took a break [from gambling], I’d be bombarded with offers. You can’t watch any kind of sporting event without being bombarded with ads.”

[ Gambling a problem for one in 30 adults in Ireland, higher than previously thought - ESRI ]

Early on, when he was in Portlaoise, he requested his information file from one of the large gambling companies under GDPR legislation. “I got called down to reception in the prison and I got handed a box, not an envelope, a box. I was walking out the door and the officer called me back: ‘You can come back for the other one.’”