Jamie Cassidy, the Liverpool starlet turned drugs conspirator: ‘In jail, some say lads want to be a footballer or a dealer. I've been both'

New York Times

11-07-2025

Jamie Cassidy remembers the exact date he realised his life as a free man was about to end.
It was October 17, 2020, the day Virgil van Dijk suffered the same appalling knee injury against Everton that had effectively ended Cassidy's own promising football career decades earlier.
Cassidy, who won the FA Youth Cup with Liverpool in a team that also featured Jamie Carragher and Michael Owen, and trained with the England squad at Euro 96, had long since retired when he sat down to watch that Merseyside derby five years ago at his home in Knowsley on the outskirts of Liverpool.
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Shortly after the match finished, he received a distressed phone call from the daughter of his older brother, Jonathan; one telling him he had been arrested on drug charges at Manchester Airport upon his return from Dubai, where he had spent most of the summer in hiding.
Cassidy knew for certain the game was up for both of them when a solicitor showed him a copy of a police report the following Monday morning. French investigators had busted the EncroChat messaging service that he and his brother were using to communicate with drug cartels in South America. Jonathan's handle was WhiskeyWasp and Jamie's was NuclearDog. Both names were all over the file, but it wasn't until November 5, at 6.30am, that a small army of police appeared at his door with an arrest warrant, proceeding to handcuff him sat on the couch in his front room.
As he was interrogated at a police station 40 miles away in Ashton-under-Lyne, Greater Manchester, Cassidy remembers his eyes glazing over, knowing the evidence in front of him could send him away for a very long time.
'The minute you get arrested, your mind takes off like a high-speed train,' he tells The Athletic. 'They're passing me these photographs and I'm thinking, 'Wow, these know everything'.'
Placed on remand, Cassidy thought he was going to HMP Forest Bank near Manchester, where his brother was being held. Instead, he was escorted back towards Liverpool on a journey that took him past his home near the M57 motorway, which he could just about see through a small window from one of the van's holding cells.
'I'm saying to myself, 'Don't look across', because when Jon got arrested, I've seen the impact it had on my mum and dad as well as Jon's five kids, and his partner,' he recalls. 'But I look anyway and I know my whole family are most probably in there, crying and worrying. It was the worst feeling I've ever had in my life. I know I won't be back for five to 10 years at least, maybe a lot longer.'
Cassidy was sent to the Victorian-era HMP Liverpool in Walton, the same district of Liverpool where he grew up.
The memory of his arrival in Walton is seared into his brain. After being stripped naked, Cassidy was asked to squat, and a mirror was placed on the floor to check he wasn't carrying anything in with him. He was then issued with two sets of 'greys' — the drab prison uniform — as well as a couple of white T-shirts and an orange blanket that looked and felt like it had been in circulation since the facility was opened in 1855. Inmates called the blanket 'Itchy and Scratchy'.
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It was at the height of a second Covid-19 lockdown and the virus was ripping through the prison community. This meant isolation and real hard time. Cassidy was unable to shower for the first six weeks, spending that period confined to a space no bigger than a small bathroom for 24 hours a day.
The routine did not improve that much for the first 18 months. Visits were not permitted. There was no gym or yard access. The cells did not have bedsheets or pillows. There were no windows and, at night, temperatures plummeted, with elements from the Irish Sea blowing in.
The only thing Cassidy could do was lay there on a bare mattress, thinking about the decisions he'd taken in his life, staring at a television that was broken, frustrated that the kettle also needed fixing. When he told a screw that nothing worked, he replied: 'Welcome to Walton, lad.'
In March 2024, Cassidy admitted he was paid a wage for his 'managerial' role in the smuggling of 356kg of cocaine into Liverpool from the Netherlands, and was sentenced to 13 years and three months in prison.
The drugs had a street value of £28million and he was described by the UK's Crown Prosecution Service, the body responsible for bringing charges, as the 'book-keeper' due to his responsibility for deliveries and collections, mainly across the north of England.
Though his brother, whose appeal against a jail sentence of 21 years and nine months was rejected in June, was considered the more senior figure in the conspiracy, much of the media's focus fell on Cassidy given his past life as a footballer.
The fact that he was not a high-profile player became an intriguing element of the story. Carragher had singled out Cassidy in his autobiography as someone who 'would have been a certain regular' had it not been for two serious injuries, but much of what had happened since was still untold.
Cassidy was released on parole from HMP Thorn Cross near Warrington last month. Amongst the judge's considerations at sentencing was his behaviour during his time on remand in Walton, where he became a 'listener' for the Samaritans, helping suicidal prisoners pull away from their darkest thoughts. The judge also accepted the remorse and 'shame' expressed by Cassidy as 'genuine and really quite profound', having come to understand the impact of his decisions as a dealer amidst a prison population beset by drug problems.
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The Athletic covered Cassidy's case at his sentencing, trying to fill in the significant gap between the moment he left Liverpool to join Cambridge United in the third tier of English professional football and appearing in an encased dock at Manchester Crown Court a quarter of a century later.
Cassidy read our reporting and made contact, offering to speak in more detail about what happened to him between the ages of 22 and 42, as well as the effect prison has had on him. Three conversations followed, and in the first of those, he concluded he had spent almost all of his adult life, 'completely lost'.
Cassidy was trim, courtesy of his time in the prison gym, and he looked every inch a former footballer. Yet he did not feel like one in the truest sense because his career was cut short so abruptly.
A 2024 study suggested only six per cent of academy footballers become professionals in England's lower leagues and even fewer establish themselves in the top flight. It is a dispiritingly low success rate, but there are, at least, more safety nets for youngsters who do not make the grade now. In Cassidy's time, the pre-academy era, there was next to no assistance for players dealing with rejection or setbacks.
Cassidy came closer than most to the promised land. At the start of the 1996-97 season, he was given the No 22 shirt in the Liverpool squad. Owen took 18, Carragher 23 and David Thompson, 25. That latter trio made 1,090 appearances at Liverpool between them; Cassidy, despite featuring in friendly matches, was the only one who did not make a full debut.
He does not blame football or anyone but himself for his decisions, and he is certainly not looking for sympathy, but he knows when his problems started. 'Nobody put the Encro in my hand but me,' he stresses. Yet he believes players, parents, advisors as well as the clubs can learn from his experiences, as well as the impact they have had on other people.
'The footballers especially,' he adds. 'Because I was a footballer and I was so close. If it wasn't for injuries, I think I would have played 15 to 20 games for Liverpool in the 1997-98 season and my career would have taken off. But I didn't have a plan B. Everything rested on football. I spent nearly 12 years at Liverpool, but when I left, I couldn't change a plug and suddenly I was out like an old stray dog.'
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The only sign of emotion from him at sentencing came when the judge mentioned one of his daughters, who was in the process of being diagnosed with a life-changing medical condition. It pains him deeply knowing he hasn't been around for the last five years to help her.
'She was 16 when I was locked up and she was glued to my hip,' he says. 'As a parent, you've got to be there for your kids and I wasn't when she was diagnosed.'
He would also look across the courtroom at his parents, who were dealing with the pressure of having two sons facing a long time locked up. Cassidy was concerned about their health, wondering whether they would live to 70.
Cassidy was released from Thorn Cross on June 11, and a day later, his father, Tommy, died following heart problems. He was 71. The terms of his parole mean that until February 2026, he is unable to leave his home between 7pm and 7am. In the end, Cassidy was grateful he could be with his father when he slipped away because it came at a time when the restrictions on his own life were lifted. While he was able to attend the funeral and deliver the eulogy on July 2, his brother, still assigned to a category A prison, was not.
'The pressure of having two sons in prison must have been really, really hard on him, but he was always supportive, coming to see me whenever he could and wherever I was,' Cassidy reflects. 'I feel fortunate I was there when he died, but I wish I could have been around for him more in his final years. The only person to blame for that is me and I'll have to live with it.'
As Cassidy's case unravelled in court, many of the reports included a photograph of him as a young boy, sitting on a ball at Melwood, Liverpool's old training ground. When assessing the image in prison with a psychologist, it would only evoke sadness because it made him think of opportunities that once seemed endless.
For Cassidy, it was always about football, but he was also aware that a career at the highest levels of the game would have allowed him to look after his family financially. 'You are put in a bracket: you are going to be this, you are going to be that,' he says.
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In his teenage world, that meant playing for Liverpool's first team, as well as England, who he represented through the junior levels. He attended Lilleshall, the former site of the English Football Association's school of excellence in Shropshire, for two years from the age of 14, where he was a pupil alongside Carragher.
His talent had been marked at an even younger age when he was selected to appear in a coaching tutorial featuring John Barnes and Bryan Robson. Cassidy can remember returning to school in Walton, where he watched the VHS video with classmates.
He would soon choose Liverpool ahead of Everton, the club he grew up supporting, having lived in City Road, close to Goodison Park. He had attended Alsop High School, where future Liverpool manager Gerard Houllier taught when he lived in the city decades previously.
Cassidy travelled on the Everton team bus to the 1989 FA Cup final, having been given a shirt signed by his hero Graeme Sharp, but he felt Liverpool were less pushy, and he enjoyed the training more under youth director Steve Heighway.
His stock at Liverpool was so high that at the age of 10 or 11, he was invited to Melwood during the summer holidays to work with the young professionals. The senior coaches liked the look of the boy everyone called 'Cass', and sometimes Ronnie Moran and Roy Evans let him join the last 15 minutes of sessions with the first team. Cassidy was an aggressive midfielder, but he was also left-footed and that made him stand out.
After scoring for an England junior team against Scotland at Wembley, the summer of 1996 was a significant one. After winning the FA Youth Cup with Liverpool in a team that included Carragher, Owen and Thompson (the opponents in the final West Ham United included Frank Lampard and Rio Ferdinand), Cassidy was called up by England's then manager Terry Venables to train with the senior national squad during the European Championship, held in England. It made him proud that he could source tickets for his dad and brother, Jonathan, at Wembley, just behind the substitutes' benches.
He has vivid memories of Paul Gascoigne dancing down the aisle on the team bus singing 'Three Lions', and on racing nights, when Cassidy lost some money, some of the other players insisted on covering his costs. The experience increased Cassidy's belief that he was destined to become an international footballer. Venables spoke to him regularly and the other players made him feel like he was a valued part of the squad.
'They were the best weeks of my life,' he says. 'None of the young lads were there on holiday. We played an active role in training, as well as the social side. It felt like I was close to making the jump. (Terry) Venables made it clear to each of us that if we carried on doing well, we could be in the full squad for the World Cup in France later, or the European Championship in 2000. Two years later, Rio got selected and Frank wasn't far behind him. Thommo also got called up to the England squad (in 2002). I was the only one that didn't.'
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The summer of 1996 finished with England losing to Germany on penalties in the semi-final and Cassidy moving on to the under-18s version of the same tournament, where England came third behind a France team inspired by Thierry Henry and David Trezeguet. Carragher did not get selected for England, but this meant he was back at Melwood where he was able to push himself in front of the senior selectors. With a full pre-season behind him, Carragher became the first of Liverpool's exciting young local players to break into the first team.
Cassidy thought the worst of his injury problems were already behind him, having snapped his tibia nearly two years earlier. On his return to football, he felt stronger physically and mentally than ever before, but just as he was pushing to break into the first team, he felt his knee pop during a friendly match against Tranmere Rovers at Melwood. The specialist who told him he'd ruptured his ACL explained the injury to him like this: 'Imagine getting a piece of rope and holding it tight in both hands, getting a brand new sharp knife, and just slicing it right in the middle.'
Cassidy remembers the tearful drive home from the clinic in Shropshire and asking, 'Why me?' His father replied, 'Why not you, lad?'
Cassidy loved his father, who, he stresses, was always there for him, but it was the only meaningful conversation he had with anyone about his feelings in relation to the injury or the direction of his career. 'It was a different time,' he says. 'If you had a problem, you had to try and get on with it.'
That injury represented a fork in the road for Cassidy.
He had previously signed a two-year deal with Liverpool, even though the club wanted to keep him for three. He was backing himself, thinking that sooner rather than later, he would be a regular in the first team and his performances would allow him to negotiate an even better deal. Instead, he was now fighting to save his career and time was running out on any security that he had.
Despite a dozen operations, he could not control the swelling on his knee. Meanwhile, the first-team manager, Roy Evans, was fighting to stay in a job, along with his staff. With such pressure, it seemed that fewer people at the club were willing to fight his corner. When Gerard Houllier replaced Evans towards the end of 1998, Cassidy felt 'stranded'.
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'I didn't want to leave because Liverpool was all I knew, it was home,' Cassidy says. 'But when I sat down with Houllier, it was clear that wasn't going to happen. Though he told me he fancied me as a left-back and that spot was open in his team, he explained that he just hadn't seen enough of me to offer a new deal. With Roy (Evans) gone, along with all of the old coaches who knew me better, like Sammy Lee, Joe Corrigan and Doug Livermore, I had no one to speak up for me.
'It might have taken time to get my knee right, but there was surely a better chance of that happening at Liverpool. I've got no ill-feeling against Houllier because he was under pressure to bring change and he wasn't waiting around for anyone.'
Cambridge offered a way out, but he was 200 miles from home, where his partner had given birth to a son. This meant Cassidy spent much of the first year of a two-year contract travelling up and down the motorway, 'probably not being the best pro I can be'.
The more painful truth, however, was that his knee was still troubling him so much that he knew his career was coming to an end.
'You've spent your whole life thinking you're going to be a star, playing for Liverpool and England,' he says. 'And then you're at Cambridge United with a dodgy knee. It was tough to take. Mentally, no one prepares you for that.
'I bought a house near Huntingdon Racecourse and when I was not going home, I was sitting there, alone in my thoughts.'
Cassidy agreed a settlement with Cambridge and after a brief spell with Northwich Victoria in the Conference (now the National League Premier), he joined Burscough in the Northern Premier League on £60 a week, which supplemented his income working for his father's building firm. His heart wasn't in it anymore and he would quickly move on from the sixth tier of English football, attempting to find some enthusiasm by playing with his mates in the Liverpool Sunday League. The scene, however, presented very different challenges.
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'You'd see bags on the touchline with guns and knives inside,' he says. 'The centre-forward would get knocked out from a corner and the referee would be terrified to send certain players off. It wasn't for me.'
For a while, he would still try to play five-a-side, but sometimes, it would take him a fortnight for his knee to recover. Cassidy admits he came to 'hate football'. He knew he could not bear to watch Liverpool, where mates like Carragher had established themselves in the first team, winning multiple trophies, as they did in 2001. He had drifted from his old social scene altogether, cutting himself away from a circle of friends he used to be so close with at Liverpool.
'I was pleased for those lads because I'm not a jealous person,' he insists. 'But all the time I was just thinking, 'I should be there with you on that journey'.'
Cassidy told Manchester Crown Court that he became an international drug dealer through opportunism. Over the years, the building trade had brought him into contact with Liverpool's criminal underworld. A friend in the drugs trade had fallen ill, but before his death in the summer of 2020, the friend, having moved into one of Jonathan Cassidy's properties, was able to guide the brothers through the business.
The former footballer says he did not wake up one day and choose to be a dealer. 'Slowly but surely, you're helping them out by getting involved, but it wasn't a decision,' he insists. 'It happens over a period of time. In jail, some say lads want to be either a footballer or a drug dealer. Unfortunately, I've been both.'
Cassidy admits he was a cocaine user and this made the crossover into dealing easier. He says he also turned to alcohol to change the way he felt. He had invested most of his earnings from football in property and though he had a pension, it was only just enough to keep his head above water. It felt like he never had enough cash.
A drug deal worth tens of millions of pounds would potentially solve any financial problems. In court, it was revealed that Jonathan Cassidy had compared himself during one EncroChat conversation to the Mexican drug lord Joaquin 'El Chapo' Guzman after watching an episode of Narcos and discovering they shared the same birthdays.
Jamie's role in the conspiracy was keeping tabs on who owed what to whom and taking collections, as well as transporting the cocaine from place to place once it had landed in Liverpool from Rotterdam.
After his arrest, he says he was advised by his legal team to fight the evidence due to arguments over the way warrants were obtained following the busting of EncroChat. This meant he spent nearly four years on remand until his case was heard.
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As a child, he had gone past the prison in Walton countless times, wondering what lay beyond the high, brooding walls. Now he was about to find out.
Cassidy is small, but he is athletic and can handle himself. Even so, he admits he was 'scared. Anyone who tells you they are cool when they go in is lying. The place is a dangerous place to be. It's like a pressure cooker that can go off any time. You've got to keep your guard up 24/7'.
As a prisoner, he witnessed inmates being slashed and assaults on staff. Through his role with the Samaritans, he would hear prisoners talking about having experienced sexual abuse. Some of the stories were from murderers, facing 30- to 45-year stretches. On more than one occasion, Cassidy helped pull someone away from attempting suicide and that counted in the judge's thoughts when it came to sentencing.
He would learn more about himself through the experiences of others. Over the previous 20 years, he had not spoken to anyone about the 'trauma' of seeing his football career nose dive as rapidly as it did. 'Up until the age of 42, I didn't understand myself because I'd never dealt with what had happened to my football career,' he reflects. 'It led to a series of bad decisions.'
He is more confident talking about it now, however, and clubs from a variety of sports have invited him to talk to their younger players. Motivational speaking is something Cassidy would like to dedicate his time to, but he understands it might take time for others to trust him again, especially with his sentencing last year seeming so fresh.
He has, nevertheless, been encouraged by initial responses. Following one talk, he received an email from the organiser, which described his session as being not only 'incredibly emotional but also incredibly inspiring, leaving a lasting impression on everyone who attended'.
On the prison wings, he was confronted by the consequences of his actions because addiction was rife.
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'A lot of lads use drugs and drink to remove the bars and take the time away,' he says. 'But I wanted to feel the pain of every day so I'd never come back.'
When he reflects on the last five years, his thoughts drift much further back. In jail, he underwent EMDR psychotherapy to try to get to the root of his problems and the findings led back to his injuries.
'Mentally, physically and emotionally, I feel like a new person now,' he says. 'Being so clear-minded has helped me deal with my dad's death.'
His family has been supportive of him throughout his time in prison and they have never made him feel like he has to rebuild his relationships with them.
He feels differently, especially in relation to his children.
'I got through jail, but what comes with it is more traumatic because of the effect it has on your family,' he says. 'It's not only the prisoner who does the time. My mum and dad, my missus, and the kids did a different type of jail. They're stressing all the time. There's a lot of anxiety and worry. You can't make up for creating that life for them, but you can try.'
(Top image — Illustration: Will Tullos / The Athletic, photo: Getty Images)