James Chester was born in Birchwood, Warrington and he went to his first Manchester United match aged six.
Two years after United had played Rotor Volgograd at Old Trafford in 1995, which was Chester’s first game, he had joined the Reds’ academy. Chester had always dreamed of representing United and he now had the opportunity to realise his ambition.
Chester quickly rose to prominence in the club’s youth ranks. He played in the 2007 FA Youth Cup final, he was named United’s U23s’ academy Player of the Year by Ole Gunnar Solskjaer and he made his first team debut under Sir Alex Ferguson in 2009.
Chester was eventually sold to Hull City in 2011 for a transfer fee that Ferguson has openly called ‘an absolute steal’.
Ahead of United’s latest academy stars playing in the 2022 FA Youth Cup final, Chester sat down with the Manchester Evening News to reflect on his career, which highlights an exciting path away from United, for any academy players that may need it.
“I got scouted playing as a right-winger. I don’t quite know what age I found myself playing centre half,” Chester explained to the MEN, while he relaxed in Stoke’s team hotel ahead of a Championship fixture against Reading.
“I think when you’re young they like to play you in different positions anyway. I think probably quickly found when I was at the academy, there were a lot more flamboyant players than me. Centre half probably complemented the kind of player I was.”
Chester might have started playing on the wing, but he found his calling at centre-back. He began to excel in defence in United’s academy and he progressed through the club’s youth levels. He admits that United provided an excellent education.
That education eventually enabled Chester to play an instrumental role in helping United reach the 2007 FA Youth Cup final. The FA Youth Cup is the pinnacle of academy football and United have won the competition (10) more than any other club.
United’s U18s have made the final for the first time since 2011 this season and they’re looking to extend that rich history.
When reflecting on his time in the academy, Chester explained United’s success in the competition is no coincidence. “As soon as you become a scholar, you’re made aware of how important the competition is for the football club,” Chester said.
“The history club has with the competition, it’s a really big deal. It’s probably quite nerve-wracking to be involved at first. I wouldn’t say the crowds as such made it nerve-racking but it’s more the importance that the club put on it and the history they have.
“They talk to you, tell you its importance and the manager and the first team players took a real interest in the Youth Cup.”
When United made it to the FA Youth Cup final in 2007, the side was captained by Sam Hewson, and it included Chester, Danny Welbeck, Danny Drinkwater and Febian Brandy. The latter was particularly exciting and tipped right for the top.
United beat Arsenal in the semi-finals of the competition that season and Liverpool awaited in the showpiece, but United would lose the final on penalties at the end of the two legs. Chester is able to recall he was ‘desperately disappointed’, even 15 years later.
“When joining United at the age of eight, I was made well aware of the rivalry between United and Liverpool. We were told how important these games were and Paul McGuiness was a large factor in all of our careers growing up at that time.
“We were all desperately disappointed we didn’t win the cup final, but the advice that he’d always give us, regarding going on to have careers maybe softened the blow a little. It’s probably been proved correct if you look at the two squads from that day to now.”
Chester explained that McGuiness, who is currently Head of Academy Player Development at Leicester, was one of the ‘main instigators’ in teaching the history of United, and he said ‘you couldn’t ask for anyone better’ to learn from.
He also lauded the influence of Solskjaer and Warren Joyce. “Playing under Ole as a United fan was something quite special,” Chester explained. “You hung on his every word for the respect that you had for him.
“He had an awful lot of time for us as a team and for players as individuals. Warren was probably the ‘bad cop’ of the two. He would get you ready for being away from United and he installed a lot of hard work and character in us with the sessions he put on.”
It is the ultimate ambition for players in United’s academy to make a full debut for the club and Chester achieved just that in 2009.
Chester got that moment in the second leg of the semi-final of the League Cup against Derby. Chester came on as a substitute for Gary Neville with 20 minutes to go and he shared the pitch with Cristiano Ronaldo under the lights at Old Trafford.
“It was incredible,” Chester explained when asked about that night. “For myself personally, for being there from such a young age, to go all the way through the age groups and senior appearance was what dreams were made of.
“Being a United fan growing up, still to this day that’s something no one can ever take from me. I think for my family more than anything, the amount of sacrifice and travel and hard work they had to put in, taking me to train three or four times a week.
“It was a satisfying moment to do that for them as well.”
Chester joined Peterborough – managed by Ferguson’s son, Darren – for a one-month loan shortly after making his debut. He was named U23 Academy Player of the Year by Solskjaer at the end of that season and was excited about the next campaign.
Chester joined Championship side Plymouth with a view to accelerating his development, but disaster struck in just his third appearance for the club. Chester sustained cartilage damage and returned to United for his rehabilitation.
After recovering from the injury, Chester joined Carlisle on loan for the 2010/2011 season. Time was now ticking on his United contract and he knew had to make it count. “Each loan move took on a different significance,” Chester admitted.
“Going to Carlisle, I was aware that I was going into the last year and that the likelihood of me staying [at United] was probably growing slimmer. It was important for me to go out and play well and perhaps earn a career somewhere away from United.”
Chester made 24 appearances for Carlisle and earned a transfer to Hull the following summer. “James had a number of injuries over a long period and we ended up selling him to Hull City fin 2011,” Ferguson wrote in his book years later.
“He went on to play over 170 games in the next four and a half seasons and turned out to be an absolute steal.”
The final page of his chapter at United had been written but Chester was only getting started. “I think it was fairly easy to accept I could see the bigger picture,” Chester recalled. “It was my dream to play for United but having a career was close second.
“I’d offer any advice to someone in a similar position to try and see further down the line and see what can be achieved elsewhere. Take all the good learnings you’ve had from United, because not everywhere is run the same way, and be the best version of you.
“Even if you don’t make it at United, it’s the highs and the lows that come with it along the way.”
There have been plenty of highs in Chester’s career since leaving United. He helped Hull achieve promotion to the Premier League, he scored in the FA Cup final against Arsenal and he captained Aston Villa, leading them back to the top flight.
Chester has over 400 senior appearances and he also played every game for Wales at the 2016 European Championship. Wales defied the odds that year and made it to the semi-final of the competition, only to be beaten by eventual winners Portugal.
Chester’s first taste of the Premier League was at Hull and he blossomed under Steve Bruce. “Playing in the Premier League was incredible for me because growing up you never quite sure how far your career is is going to go,” Chester said.
“To have the opportunity to play at that level and against some of the best players in the world was amazing. The vast majority of the success I’ve had in my career has come under Steve. He just let you go out and play. It was always enjoyable to play under him.
“Steve puts a good group of people and players together and I think that camaraderie took us a long way with the promotion first of all, then staying in the Premier League the next season and reaching the FA Cup final.”
Chester opened the scoring at Wembley in that final but Arsenal claimed the trophy. Chester would make his international debut for Wales shortly after that match in 2014 following a phone call from Wales manager Chris Coleman.
“I think playing internationally was never something on my radar,” Chester said. “I never did it through youth team level. I was always focused on just having a career in football, but when I got the phone call from Chris, I was happy with where I was.
“It was just an opportunity to try something new and I’m really glad I did.”
Wales won their group ahead of England and shocked the world when beating Belgium in the quarter-finals. Chester started in every match in a three-man defence and Wales were met by thousands of supporters when they eventually returned home.
Chester had helped his nation create history. “It was surreal really. I think a lot of us probably looked at the end of it and thought it’s not going to get as good again,” Chester recalled. “It [Wales] brought some of the most successful and happiest times of my career.
“It was an incredible journey playing in the Euros and being able to experience that with people who are now my friends for the rest of my life. To have your family there for each game, it’s just something that will always bring a smile to my face.”
Chester signed for Aston Villa after that tournament. Villa had just been relegated from the Premier League and he was signed to help the club back to the top flight. Chester would spend three years at Villa Park and he left as a genuine club hero in 2020.
“I had a wonderful time at Hull with the success we had, but I think my time at Villa feels different for different reasons. I joined with the club in a difficult position. I just felt the responsibility and the respect from the staff and the fan base,” Chester said.
“It was the best time in my career. I think the way I played and the way I presented myself, the fans could see that’s how they wanted their club to be represented. I took great pride in trying to do that every game.
“To have the opportunity to play for such a big club, the history that they have, to play in front of 35,000 every week was something that was really special. It felt justified to get promoted back to the Premier League where the club was always meant to be.”
Villa supporters will always remember ‘Chezzy’. The centre-back was a stalwart during the club’s days in the Championship and he sacrificed his own body in the club’s final season in the second tier to give them a chance of promotion.
Chester had sustained a knee injury that season, but with Villa short of options at centre-back, he continued until late January when reinforcements were finally signed. He didn’t play again after January and he reappeared for the play-off final win at Wembley.
Chester lifted the trophy with Jack Grealish, who had taken over the armband in his absence, before climbing down from the Wembley steps and heading towards the mixed zone. Chester answered questions from the press and soon had a tear in his eye.
“I’ve damaged my body indefinitely,” Chester told reporters at the time. “It’s something I’m going to have to manage for the rest of my career. Hopefully I can look after it and play for as long as possible. It is what it is, I’m a professional.
“It’s been tough and really painful at times but it’s just how I’ve been brought up at home. I felt it was my duty as such to continue, being the only centre half.”
Few were aware of the extent of Chester’s sacrifice and it sealed how he would be remembered at Villa. Chester made his return from injury against Liverpool in the League Cup in December 2019 and that was his last appearance at Villa Park.
Chester didn’t know that would be his last chance to say goodbye at the time but he still reveled in that special return. “To think back on it, to have the whole crowd singing my name was really quite a touching experience,” Chester said.
“To have them acknowledge what I’d put myself through for the better of the club.” Chester left Villa six months later to sign for Stoke, where he’s still currently playing. He’s not playing as regularly but he remains a leader among men.
Chester, 33, admits he enjoys being a positive influence on Stoke’s youngsters and he laughed as he admitted that he isn’t prepared to give it up just yet. Having a career in football is all Chester has known since joining United’s academy aged eight.
When asked for his final advice for United’s youngsters, or anyone at that stage of their career, Chester said: “Don’t get too high with the highs and don’t get too low with the lows. Learn from the experiences and see how far that takes you.”
That advice has taken Chester to places he could only dream of when supporting United growing up.
Chester is proof you can forge an excellent career after leaving United’s academy.