The Spoiler’s “Shouldn’t have let him go” XI
The most regrettable transfers in Premier League history
It’s the January window, which means plenty of players are going to trade hands. Some clubs will end up paying far too much money for their new blood (Manchester City have already got the ball rolling on that one), while others will land a player who proves to be a bargain and a regrettable loss for their former employer. A classic example of the latter is Denis Law: Manchester United decided to let their second highest goal scorer of all time leave on a free to rivals City. Law only spent one year at City in his second spell before retiring, but his last goal came in the last game of the 1973-74 season against United. The red side of Manchester needed a win to stay up, but a Law back heel in a 1-0 win confirmed their place in the Second Division for the next season.
With this case study in mind, here’s the Premier League ‘Shouldn’t have let him go XI’…
Brad Friedel (Liverpool to Blackburn, 2000, free)
Friedel only managed 30 starts for Liverpool in three years before he was allowed to move on a free to Blackburn, after failing to displace Sander Westerveld. Since leaving Merseyside, Friedel has been one of the most consistent keepers in the league, while Liverpool have been through Westerveld, Dudek, Chris Kirkland, Pegguy Arphexad and Scott Carson, before settling with current shot stopper Pepe Reina.
Steve Finnan (Fulham to Liverpool, 2003, £3.5m)
Finnan was a key figure in the Cottagers side that won the Second Division and First Division and was a member of the PFA Team of the Year in his first season in the Premiership with them. He managed over 200 appearances for Fulham before moving to Liverpool and winning the League Cup, FA Cup and Champions League in his 5 years on Merseyside.
Jonathan Woodgate (Leeds to Newcastle, 2003, £9m)
In January 2001, Leeds were top of the Premiership. Two years later, they found themselves fighting a relegation battle. Then came the sales of Lee Bowyer, Robbie Fowler and their best defender, Woodgate – unsurprisingly their poor form continued. The following season Woodgate’s value to the team was all too evident when Roque Junior was brought in to fill the gap. Junior looked like he had money on a Leeds relegation as the club conceded 25 goals in the 7 games he played in.
Matthew Upson (Arsenal to Birmingham, 2003, £1m)
Upson only managed 20 league starts in nearly six years at Arsenal before he was sold for half the price they had previously paid for him. He excelled at Birmingam before a £6 million switch to West Ham, where his performances have been rewarded by a call up to the England team. Recent reports have suggested that following the uncertainty of the future of ex-captain William Gallas, Professor Wenger is keen to spend over £10m on bringing him back to Arsenal. If he does rejoin the club, maybe he’d have more luck starting if he changed his name to Mathieu Upsoné.
David Unsworth (Sheffield United to Wigan, 2007, free)
Mr Unsworth wasn’t the biggest success at Wigan – he only managed 10 games for the club. He did, however, manage to score the winning goal with a penalty in Wigan’s last game of the season to keep them in the Premier League. And the side who went down at Wigan’s expense? Sheffield United. They were unduly beaten that day and have been whinging about West Ham’s use of ‘everybody-owns-him-nobody-really-owns-him’ Carlos Tevez ever since.
David Bentley (Arsenal to Blackburn, 2006, undisclosed)
DB also fell foul of Wenger’s reluctance to give English youngsters a chance, and was deemed surplus to requirements after just one league start for the Gunners. Blackburn signed him following a successful loan spell, and soon after he proved his ability as a quality player and after seven goals and 13 assists in his first full season. Another year of sterling performances later, and Spurs broke the bank to pay £15m to bring him back to London. Despite not performing at his best this year, he managed a stunning 40-yard volley in the 4-4 draw with the Gunners in October – a game that has proved a catalyst for Arsenal’s indifferent run ever since.
Michael Carrick (West Ham to Spurs, 2004, £2.75m)
After failing to bounce back in their first year following relegation from the Premier League, it was understandable one of the Hammers’ best players might want to move back amongst the Premiership elite. One would have thought West Ham could have negotiated a better deal than £2.75m though, especially as they let him go to rivals Tottenham. Despite regaining their top flight status a year later without the midfielder, the real size of their mistake was made apparent when Spurs moved him on for £18m after just 2 years at the club.
Lassana Diarra (Arsenal to Portsmouth, 2008, £5.5m)
Diarra showed his potential at Portsmouth and has impressed in Spain since his move to Madrid. While Chelsea allowed the talented defensive midfielder to leave for rivals Arsenal, it is the latter who made the biggest mistake in selling him again – after just six months at the Emirates. Arsenal’s main problem this season has been a lack of steel in midfield, and following the departure of Mathieu Flamini in the summer, their inadequacies were further highlighted. How Wenger wishes he kept him now.
Nick Barmby (Everton to Liverpool, 2000, £6m)
Okay, not on the same level of idiocy as some of the other deals, but also not the best piece of business. Liverpool won the treble in Barmby’s first season at the club – he scored 10 goals in the process – while Everton won diddly squat. And to add insult to injury, Barmby scored in the win against his former club in the Merseyside Derby that season.
Eric Cantona (Leeds United to Manchester United, 1992, £1.2m)
Leeds manager Howard Wilkinson rang Fergie to enquire about the availability of Dennis Irwin. The red-nosed Scot knocked back the idea and set up a deal for Eric Cantona instead. The Frenchman inspired Man United to their first league title in 26 years and their first of four league crowns in his five years at the club. During the same time, Leeds won nought. How Leeds fan must wish Wilko never made that phone call.
Jermain Defoe (Spurs to Pompey, 2008, £7.5m)
This birth could easily have gone to Spurs again for either letting a 19-year-old Peter Crouch leave for £60,000 in 2000, or selling their prize asset Teddy Sheringham to Manchester United in 1997 for £3.5 million. However, both mishaps aren’t quite as stupid as selling Defoe for £7.5 million before buying him back a year later for double the price. To be fair though, Danielle Lloyd’s ex failed to force his way past Dimatar Berbatov or Robbie Keane in the team at the time, and Mr Levy has engineered the deal so that Tottenham will end up paying virtually nothing for the striker.
Research: Danny Harris