It is often the ultimate pub quiz question. Who is the youngest player to ever play for Liverpool? Well, the answer is Jerome Sinclair. Yes, remember him?
His career began at West Bromwich Albion before he moved to Liverpool at the age of 14. Then, aged just 16 years and 6 days, he came off the bench to make his senior Reds debut, replacing fellow teenager Samed Yesil in a 2-1 win over Albion in the League Cup on September 26, 2012.
Injury curtailed a season thereafter, but he was soon back with a bang, firing in the goals for Liverpool's youth teams at various age levels. That impressive form led to the then Reds boss Brendan Rodgers claiming the Anfield club had a 'bright' future ahead of them thanks to Academy stars like Sinclair.
After an eye-catching performance for Liverpool U21s against Chelsea, a match in which the winger scored, Sinclair received some big praise from Reds great Jamie Carragher.
READ MORE: Dominik Szoboszlai may change Liverpool transfer narrative with more surprises on shortlist
READ MORE: Manchester United drop £170m hint that points to next FSG move at Liverpool
He said: "It was an outstanding finish. He left the defender for dead and then showed great pace and composure on his weaker foot.
"Another member of this squad, Sheyi Ojo, has gone to Wigan on loan. That’s the next step for Jerome. I think it’s a big ask for Jerome to go straight into the Liverpool first team. There are enough strikers there at the moment.
"He needs to go out on loan, get games under his belt, and prove himself in men’s football. Hopefully, at the start of next season, he will go on the pre-season tour and show Brendan Rodgers what he can do."
Before he added: "Hopefully he will go on to have a great career, and I can tell people I played with Jerome Sinclair.
"They have specialist coaches at the Academy at all levels. Robbie Fowler, Steve McManaman and Rob Jones go in and pass on words of wisdom and it looks like Jerome has been listening."
Sinclair, then 18 years old, moved on a youth loan to Championship club Wigan Athletic in March 2015, where he only made one appearance before returning to the club. He made his top-flight debut for the Reds in May of that year, when he came on against champions Chelsea.
A week later, he would feature again for the Reds in a 3-1 defeat to Crystal Palace. A game that is remembered most as Steven Gerrard’s last at Anfield for Liverpool.
However, as the year drew to a close, things began to turn sour between Sinclair and Liverpool. The situation was not helped by the fact that he opted to change agents.
Aidy Ward was the man chosen by Sinclair to represent him as his Liverpool contract entered its final few months. But Ward and Anfield chiefs had history.
Just months before linking up with Sinclair, Ward infamously helped engineer Raheem Sterling’s controversial exit from Anfield. He launched an extraordinary attack on the club as he tried to force through a move to Manchester City.
Ward insisted he 'didn’t care' about Liverpool’s image and said Sterling wouldn’t sign a new deal even if he was offered '£900,000 per week'. Sterling eventually got his wish, but only after City met the Reds’ £49m asking price.
By this time, Jurgen Klopp had replaced Rodgers as Liverpool boss. And as reported by the ECHO at the time, there was a big gulf between the terms Liverpool were willing to offer and what Sinclair’s camp were demanding.
Sinclair would play for Klopp at Liverpool. He was handed a start in the third round of the FA Cup away to Exeter City, where he scored his first goal for the club in the 12th minute. However, soon after, he announced his intention to leave at the end of the season, expressing a wish to play abroad.
Sinclair’s desire to play abroad didn’t prevent Watford from coming in with a £1.5m offer at the end of that month, but it was rejected by Liverpool. In April, Bournemouth made contact and bid £4m, and while that was accepted by Liverpool, this time it was turned down by the player.
Yet no sooner had the campaign finished, and with Sinclair’s deal set to expire, he agreed to a four-year contract with Watford. A picture of Sinclair signing his deal with the Hornets was posted on the Instagram page of Colossal Sports Management, his representatives.
The Reds, via a tribunal, secured a £4m fee for the winger, who left Kop boss Klopp less than impressed with his actions.
"What we try to do is create a situation where younger players know it is not important to get the highest wages in your life in the first year of your career," he said.
"So, money talks? I like Jerome; he is a real talent, and if he wants to stay with us, no problem. If not, we cannot force it."
But the England youth international failed to shine in his first season at Vicarage Road. After one start and four substitute appearances in the Premier League, he joined Championship side Birmingham City on loan in the January transfer window.
But after making three consecutive starts, Sinclair failed to feature in his team’s next 11 games. Opening up on his Anfield exit back in January 2017, Sinclair insisted he left Liverpool for the good of his career and defended making the move to Vicarage Road.
He said: "To me, it was an exciting opportunity to further my career at a club that’s growing. I played here in an FA Youth Cup tie three years ago, and one side of the ground was missing, so you can see how much the club has progressed.
"We’re trying to cement our place in the Premier League and kick on towards those European places. It is very important for the young players here to see there is a pathway to the first team."
Still being represented by Ward, Sinclair found himself embroiled in yet more controversy on deadline day back in the summer of 2017.
He had been set to join Championship side Sheffield United on loan, only for the move to fall through. And a brilliant, insightful video from Bleacher Report revealed exactly why, with agent Ward seemingly playing a central role.
Bleacher Report was offered behind-the-scenes access to Sheffield United on deadline day, following then Blades boss Chris Wilder as he sought to conclude a number of deals before the end of the window.
The video shows Wilder speaking with his head of football operations, Carl Schieber, on Thursday morning, confirming that a move to Sinclair was 'all done', with only a signature required. Indeed, it is revealed that Sinclair's agent, understood to be Ward, has informed the club that the player is heading to Sheffield to finalise the switch.
However, by early afternoon, there was still no sign of Sinclair, with a worried Wilder sending a text to the agent to find out the situation. He discovers that Sinclair is still in Watford and calls him to try to convince him to make the move north for the season.
He is shown attempting to sell Sheffield United and their style of play to the youngster. But within a couple of hours, a text from Ward reveals that the terms of the deal have changed, forcing Wilder to pull the plug.
Wilder and Schieber reveal that the agent had asked for a doubling of his fee, which United were unwilling to agree to. A move for another of Ward's clients, then West Ham teenager Domingos Quina, also fell through due to similar issues.
Later, it is revealed that Sinclair is sitting at Sheffield train station, awaiting instructions from his agent. The move is not revived, despite Wilder insisting that the player wants to join.
In the days following the release of the video, Sinclair took to Twitter to definitely speak out about what he called a 'one-sided' and 'misleading' account.
He said: "This footage is one-sided and very misleading. I was approached, but nothing was agreed upon. I am very happy at Watford and am looking forward to the season. Don't believe everything you read or watch!"
But after just five appearances for Watford that season, the following campaign saw him sent out to Sunderland, where he played 13 matches before his loan was cut short.
"He is such a great boy, but it just hasn't clicked for him here, and that's a shame not only for us but also for him," the then Sunderland boss Jack Ross said when asked about Sinclair.
"He'll go back to Watford and then take stock and see where he goes next. I can't speak highly of him, his attitude, how he has trained even when out of the team - he has not been one bit of bother."
After returning from Sunderland, he immediately went out to Oxford for the remainder of the 2018/19 season, where he scored four times in 16 appearances to become a fans’ favourite.
A move to Dutch club VVV-Venlo on loan then followed. In 29 appearances in all competitions, he netted three times and claimed one assist.
And after making two League Cup appearances for Watford at the start of 2020/21, he joined CSKA Sofia on loan. He scored once in 18 league appearances in Bulgaria before returning to England, where he left Watford in the summer of 2021 following the expiry of his contract.
A year then passed before Sinclair, who was reportedly now no longer represented by Ward, rejoined Oxford United on a trial basis during the summer, playing his first match in over a year in a friendly against Banbury United. He would continue to feature for the U’s during the summer.
However, nothing was to come from the trial once the EFL season got underway, and the winger, who was once labelled the next Michael Owen, is without a club at the age of 26.
The clearest indication yet that Sinclair was now living a life without football came last summer when Morley’s, a chain of fried-chicken takeaways that has expanded since being founded in London in 1985, tweeted: "Welcome to the Morley’s family, Jerome Sinclair."
The company then confirmed to The Athletic in January that the former Liverpool youngster is the current owner of its Birmingham franchise. He's still the youngest player ever to pull on a Liverpool shirt in a competitive game, but it is fair to say that since leaving Anfield, Sinclair's career has not gone the way many imagined it would.
*A version of this article was first published in September 2022.
