Sports

Liverpool FA Youth Cup Winner Jamie Cassidy Served 13 Years in Jail

Published

4 weeks ago

May 10, 2026

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In recent decades, Liverpool’s youth system has gone under the radar compared with their Premier League rivals. But with Steven Gerrard, Robbie Fowler, Trent Alexander-Arnold, Jamie Carragher, and Michael Owen among their graduates, the Reds deserve credit where it’s due for producing talent that stands the test of time.

As with every talent factory, though, not everyone who comes through the grind of youth football gets their moment in the sun – there’s always a flip side to the coin. That was the case for one former Liverpool prospect, who won the FA Youth Cup alongside Carragher and Owen but went down a route of crime as his world turned upside down following two career-ending injuries.

Carragher recalled in his 2008 autobiography that Jamie Cassidy would have been “a certain Liverpool regular” if his development hadn’t been derailed. Instead, his career was over and done with within five years of receiving the golden ticket of his first professional contract.

Starlet Who Won FA Youth Cup with Owen & Carragher Retired 5 Years Later

Liverpool-born Jamie Cassidy would also go on to train with the England squad at Euro 1996, proving just how highly the now 48-year-old was regarded during his time as an up-and-coming football prodigy. He earned a professional contract in the same year but was released three years later, in 1999, without playing a first-team game for the Reds, then managed by Roy Evans and Gerard Houllier.

He then spent a year at Cambridge United, playing 10 matches in all competitions, before moving into the realms of non-league football with Cambridge City, Northwich Victoria and Burscough. It all came as a result of a damaged cruciate ligament followed by a broken leg in quick succession, which marked the beginning of a downward spiral for such a highly promising career.

By 2001, a life in football no longer seemed viable for Cassidy. So, in the same year his former youth teammates pulled off an unorthodox treble – winning the League Cup, FA Cup, and UEFA Cup (later rebranded the Europa League) – he hung up his boots for good. What followed was a 13-year jail sentence after his involvement in a drug conspiracy, a stark contrast to the future once laid out before him.

He stressed to The Athletic that nobody was to blame for his downfall when reflecting on the moment he realised he was going to Walton prison. 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 said. “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.”

It was October 17, 2020, the day Virgil van Dijk suffered the same destructive knee injury against Everton that had effectively ended Cassidy’s own promising football career decades earlier, when he caught wind of his brother’s arrest, which would lead to his own downfall for his role in a drug conspiracy.

In March 2024, as per The Athletic, 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.

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.

“Slowly but surely, you’re helping them out by getting involved, but it wasn’t a decision. 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.”

‘My Chelsea Teammate Was Tipped as Next Lionel Messi – but He Retired at 22 and Was Jailed’

One former Chelsea youth player’s life after football has consisted of trips to prison, a psychiatric ward, and, recently, an intensive care unit.

Cassidy admitted he was a cocaine user and this made the crossover into dealing easier. He explained how 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.

A drug deal worth tens of millions of pounds would potentially solve any financial problems. In court, it was revealed that Jonathan Cassidy, his brother, 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.

Cassidy was released on parole in June 2025. 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, while he had also played a crucial role in stopping multiple inmates from committing suicide.

Cassidy’s Family Problems While Serving Prison Sentence

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 still pains him 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 said. “As a parent, you’ve got to be there for your kids and I wasn’t when she was diagnosed.”

Cassidy was released from Thorn Cross on June 11, and a day later, his father, Tommy, died following heart problems, at 71. The terms of his parole meant that until February 2026, he was 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 reflected. “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. I got through jail, but what comes with it is more traumatic because of the effect it has on your family.”

Sports

Liverpool Working on ‘Fast’ Deal for Diomande, He’s Iraola’s Next Semenyo

Published

2 hours ago

June 3, 2026

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Liverpool are closing in on appointing Andoni Iraola as their new manager with an agreement already reached between the two parties.

Liverpool chiefs will have tasked the former Bournemouth boss with turning their fortunes around following a tough season on and off the pitch at Anfield.

The Reds produced a miserable defence of their Premier League title as they finished fifth and 25 points behind champions Arsenal, although they faced the heartbreaking loss of Diogo Jota, while club-record signing Alexander Isak was impacted by injury throughout the campaign.

Meanwhile, Iraola led the Cherries to sixth and Europa League football, following an outstanding second half of the season on the south coast.

The 43-year-old arrives at Anfield as one of the best young coaches in European football, and a manager who is brilliant tactically and loves to play the high-intensity football that Reds supporters love.

While Liverpool still have a lot of good players in their ranks, there will be changes this summer, with some enforced after the departures of Mohamed Salah, Andy Robertson and Ibrahima Konate this summer.

Incomings are on their way, especially in attacking areas where there is a shortage of quality and depth after Salah’s exit.

Romano: Liverpool In Talks Over ‘Fast’ Yan Diomande Deal

Liverpool’s priority is to sign a replacement for Salah this summer, and RB Leipzig sensation Yan Diomande has emerged as one of their top targets to replace the Egyptian on the right after a breakthrough campaign for the Bundesliga outfit.

The 19-year-old scored 13 goals and registered a further 10 assists this term for Leipzig, which are impressive numbers for a teenager, and reports in Germany have suggested that the club value him at up to £130m.

As well as his goal contribution numbers, Diomande has also impressed with his pressing intensity and his work rate, which prove he is a team player despite being someone who causes nightmares for defenders.

Romano has issued the latest on Liverpool’s pursuit of Diomande, who is also a target for Paris Saint-Germain, on his YouTube channel, with the player’s representatives wanting a deal wrapped up before the World Cup begins on June 11.

He said: “Liverpool are in negotiations. They are on it, for sure. PSG are also speaking with the player’s camp. The battle is on.

“I can tell you the preference on the player side is to do the deal fast before the start of the World Cup so Diomande can go to the World Cup without thinking. They will try to accelerate the deal before the World Cup.

“It will depend on Leipzig. It is never easy to negotiate with them but Liverpool and PSG are both working on it.”

Diomande Would be Iraola’s Next Semenyo

Semenyo exploded under Iraola at the Vitality Stadium prior to his move to Manchester City, scoring 10 Premier League goals this season before his transfer in the January window.

Like Diomande, Semenyo showed he could play on both flanks during his time with Bournemouth, and he caused big issues for his opponents.

Germany-based journalist Seb Stafford-Bloor is someone who has watched a lot of Diomande during the 2025-26 campaign, and he even said himself that the Ivorian ‘reminds me of Semenyo’.

It appears as though Diomande isn’t going to come cheap this summer, but he has the attributes to thrive under Iraola at Anfield if a move does materialise.

Sports

Gilberto Silva Ranked Gerrard, Lampard and Scholes From Worst to Best

Published

2 hours ago

June 3, 2026

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One of the biggest debates in English football, one that still rages today, is who was the better player: Paul Scholes, Steven Gerrard or Frank Lampard? The question is one that has split opinions throughout the sport, with fans, players and pundits offering their takes on the subject.

All three shone in the Premier League. Scholes represented Manchester United and was key to their success throughout the 1990s and 2000s, Gerrard was Liverpool through and through, guiding the Merseyside club to the promised land on multiple occasions throughout the 2000s and 2010s, and Lampard first impressed at West Ham United before becoming a Chelsea legend, known for his goalscoring exploits as the Blues wrestled control of the Premier League from United during the 2000s and 2010s.

All three were very different kinds of players, but they’ve been compared to one another for two decades now. Former Arsenal midfielder Gilberto Silva was the latest former player to give his opinion on the trio and he ranked them from worst to best during an appearance on the podcast, From My Left.

Gerrard vs Scholes vs Lampard: Total Career Ballon d’Or Votes Compared

The number of Ballon d’Or votes Frank Lampard, Paul Scholes and Steven Gerrard received during their careers.

Gilberto’s Ranking of Scholes, Gerrard and Lampard

During his appearance on the From My Left podcast, Gilberto was tasked with ranking Patrick Vieira with Scholes, Gerrard and Lampard. The Brazilian wasted no time ranking his former teammate in first place, before then moving onto the English trio. In first place, he picked Scholes.

The two did battle during Arsenal’s rivalry with United in the early 2000s, with the two teams competing for the Premier League title. The ex-Gunner even went on to describe Scholes as the toughest player he ever had to face off against. Speaking about the former United star, he said:

“He was very smart. Every time I had to face him in the middle, the challenge, he was very smart. These players raise your game and you have to raise your standard to face them.”

Scholes is considered the best midfielder in Premier League history, so there won’t be many who disagree with Gilberto’s decision to rank him ahead of Gerrard and Lampard. In second place, he picked the Liverpool man. Over the years, Gerrard earned a reputation for his ability to lead Liverpool through the toughest of circumstances. He is beloved by the Reds faithful and there aren’t many fans of the club who would choose anyone over him.

Lampard Chosen Last, But Certainly Not Least

Lampard came last in Gilberto’s ranking. The former Chelsea man is the greatest goalscoring midfielder in Premier League history. He became the first player in his position to score at least 10 league goals in 10 straight seasons and always stepped up to the plate when the Blues needed it most.

He was a fierce competitor and was also a dependable leader, always rising to the occasion when John Terry was unavailable, such as in the 2012 Champions League final.

Every Current 2026/27 Premier League Manager [Ranked]

From Mikel Arteta to David Moyes, all current Premier League managers have been ranked from best to worst.

Now, out of the trio, he is the best manager of England’s golden generation midfield, with his latest achievement seeing him take Coventry City from consistent Championship playoff contention to the league title, with the Sky Blues back in the Premier League.

Sports

Dean Saunders Names 5 Managers Liverpool Should Sign Before Iraola

Published

3 hours ago

June 3, 2026

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The general consensus surrounding Liverpool’s decision to replace Arne Slot – the Reds’ latest Premier League-winning manager – with Andoni Iraola is that it is a gamble worth taking. Swapping the Dutchman’s slower, more methodical tactical style for the explosive, front-footed approach of Bournemouth’s former mastermind feels much more like a return to the Jurgen Klopp blueprint.

It was that exciting brand of football that earned the Cherries a place in next season’s Europa League, as they went unbeaten throughout the second half of the league campaign. Meanwhile, Slot was struggling to get a tune out of nearly all of his expensive new signings, including British transfer-record arrivals Florian Wirtz and Alexander Isak, as the fallen champions only just scraped into the top five.

This new era has set the wheels in motion for a fresh start under leadership that should reignite an Anfield crowd which lost most of its spark last season. However, not everyone is convinced by the bold approach. One of Liverpool’s former FA Cup winners has already spoken out, revealing the five alternative candidates he would have preferred to see appointed instead of Iraola.

Why Liverpool Have Decided to Hire Andoni Iraola Instead of Xabi Alonso

A journalist claims Liverpool didn’t miss out on Xabi Alonso.

Why Former Liverpool Ace is Against Andoni Iraola’s Appointment

Dean Saunders, who played for Liverpool in the early ’90s and won an FA Cup for his efforts, is not so sure the Spaniard is the right choice, doubting his ability to step up to the pressurised situation of managing an elite club. “Only certain people can manage Liverpool,” Saunders told talkSPORT.

“If I’m the recruitment team at Liverpool and I’ve sacked Slot, they would have thought that this bloke don’t know how to win games every week. For Liverpool it’s a disaster if you draw. At a top club the rules are different. You’ve got to win every single game and you’ve got to know how to do it.”

He added: “You think of people who know how to win football matches and know how to take the game to the opposition. They know how to break parking the bus down every week, they know how to do it.”

Indeed, the 61-year-old, who also had stints at the likes of Aston Villa, Derby County, and Brighton & Hove Albion, has a point. Iraola has never won a major trophy, never managed a club whose ambitions depend on the ultimate currency of success, while you would have to look a fair way back before seeing the last time a manager from outside of the top six joined one and was a hit.

The Five Managers Saunders Would Have Turned To Instead

Manchester City manager Pep Guardiola with the Premier League trophy

Needless to say, Saunders’ call for the Reds to try tie Pep Guardiola down to a contract just weeks after leaving his beloved Manchester City is one hell of a sensational call. But the point he was making with his list of alternatives is that he believes Liverpool should have looked towards the tried, tested, and successful head coaches first.

“Liverpool can pay the manager whatever they want. I would think, right we’re going to sack Slot who can we get?” he continued. “Jurgen Klopp, can we get Jurgen Klopp back?

“What about Pep Guardiola? Can we get Pep Guardiola? Honestly! If we get any of them two, we’re going to win games and leagues. Can’t get them. What about [Luis] Enrique? No don’t want to leave PSG. What about Mourinho? Proven winner.

“I would go through the list. [Carlo] Ancelotti, would he leave Brazil at the end of the World Cup and come and manage us? I would go through that list, before I start going into [Xabi] Alonso, [Steven] Gerrard, Iraola, young managers. I would start with the people who know how to win football matches.”

Steven Gerrard Makes Feelings Clear About Slot and Iraola After Liverpool Sack Decision

Former Liverpool captain Steven Gerrard has given his thoughts on Arne Slot’s exit from Anfield.

The Athletic report that Iraola has verbally agreed a deal to become Liverpool manager and is set to sign a two-year contract at Anfield. It will undoubtedly be a giant step for the 43-year-old, who has a glowing reputation, but has a managerial history of AEK Larnaca, Mirandes and Rayo Vallecano before his three-year stint with Bournemouth.

While silverware will be expected at Anfield, though, it won’t be number one priority next season. The Spaniard’s high-octane style of football should keep his new supporters interested for a while yet anyway, and the red half of Merseyside usually takes a lot of hits before changing their mind on their manager.