Leeds United’s fall from grace in the early 2000s is a story that the Elland Road faithful will not need repeating.
Indeed, after finishing fourth in the 2000/01 Premier League campaign, as well as reaching the Champions League semi-final that same season, the Whites were relegated to the second tier of English football just three years later – with the club in huge financial trouble after grossly overspending in the transfer market.
As a result of these financial difficulties, a number of the club’s biggest assets were sold off the following summer, including Alan Smith to Manchester United, Mark Viduka to Middlesbrough and Scott Carson to Liverpool, as well as one 18-year-old James Milner, who left Elland Road in a £5m move to Newcastle United.
Looking back on his departure in an interview with FourFourTwo in 2018, the now-Liverpool midfielder revealed his shock at then-owner Gerald Krasner’s decision to cash in on him, as well as claiming he would have liked to remain at his boyhood club for a little while longer before moving onto pastures new.
Milner said: “It was a very tough time to get relegated and there were a lot of financial things going on – things in the papers, off-field problems… you had to grow up quickly by watching the senior players and how they were dealing with everything.
“As hard as it was, I learned a lot very quickly. Within two years I’d had numerous managers, and highs and lows. By the start of my second season, Peter Reid had come in and I was sent on loan to Swindon. I did quite well there, went back to Leeds and started playing in every game.
“But then, in 2004, I turned up on the first day of pre-season thinking we were going to discuss a new contract, and someone said: ‘You’re going up to Newcastle for your medical tomorrow’. I was like: ‘Am I?’ That was tough. It was disappointing that I didn’t get to play for Leeds for longer, but to do it at all was pretty special.
“What little money the club owed me, I gave up to help them, and they got a transfer fee. So it was portrayed to me that it was in the best interests of the club [for me to leave] due to all of the financial difficulties. I thought I was going the right thing by the club.”
However, while Milner’s sale may have kept the financial wolves from the door for slightly longer, the club would ultimately go into administration once again under Ken Bates in 2007 regardless, resulting in the Whites being relegated to the third tier of English football having failed to secure promotion back to the top flight after dropping down to the second tier in 2004.
As such, with the benefit of hindsight, keeping a player of Milner’s ability at the club rather than cashing in on the teenager for a cut-price deal would have appeared to have been a much wiser move by Krasner, as the midfielder could well have made all the difference in Leeds’ 2005/06 promotion push – a season in which the Whites lost 3-0 to Watford in the play-off final.
Indeed, this loss marked a huge turning point in the history of Leeds, with the club suffering relegation to League One the following season, with it being a total of 16 years until they would return to the top flight of English football.
And, in this time, Milner enjoyed a stellar career at the very top of the professional game, going on to secure moves to clubs such as Aston Villa, Manchester City and his current side Liverpool – winning one Champions League, three Premier Leagues, one FIFA Club World Cup, one UEFA Supercup, two FA Cups, two League Cups and two Community Shields along the way.
As such, Krasner’s call on the then-18-year-old was very much a shocker by the former Leeds owner, as keeping hold of the £140k-per-week talent – who Darren Bent dubbed “ridiculous” and Jack Wilshere labelled a “legend” – could well have changed the course of Leeds’ history.