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Buying footballers can be a tricky business. You’d think that spending upwards of £20 million on a player would guarantee success: not a bit. For every Ruud van Nistelrooy there’s a Juan Sebastian Veron. It’s a bit like football’s equivalent of Newton’s law of motion in fact. Now, with Darren Bent set for a £24million move to Aston Villa, questions are arising as to which way he will go.

So as water cooler debate focuses on exactly that, we thought we’d delve into the murky box marked worst transfers of all time. Who’s in? Who’s out? David Bentley, you can breathe easy for now. But believe you me, it was a close run thing…

(Images: Getty, Rex Features)

Francis Jeffers

Everton to Arsenal; £8m, 2001

Before Wayne Rooney there was, incredibly, Francis ‘Franny’ Jeffers. The lad with the unfortunate ears was, ahem, earmarked for greatness when he made his debut for Everton at 16. A crafty striker, his displays caught the attention of Arsenal boss Arsene Wenger who memorably described him as a ‘fox in the box’. Unfortunately, following his £8million transfer to Highbury his career went into nosedive. Still holds a 100 per cent scoring record for England though – mind you, he only played the once. Still only 29, he was last seen plying his trade in Australia. Oh my.

Jean-Alain Boumsong

Glasgow Rangers to Newcastle United; £8m, 2005

Before his move to Rangers in 2004, Boumsong was hailed as a classy defender in his adopted home of France. Eyebrows were raised however, when Boumsong signed for Newcastle United just six months after his arrival in Glasgow – not least because he had moved to Rangers on a free. Despite being a French international his spell on Tyneside was desperately poor. Derided by fans for his constant mistakes, by the end of his Newcastle career he even managed to make Titus Bramble look good, such was his ineptness.

Afonso Alves

Heerenveen to Middlesbrough; £12m, 2008

When Middlesbrough bought the powerful Brazilian centre forward Afonso Alves in 2008 it was seen as something of a no-brainer. After all, Alves had scored goals for fun in Holland (his record for Heerenveen was actually better than a goal a game). His record in England, however, was quite the opposite. After showing early promise in his truncated first season (he was bought in the January transfer window), his second season was an unmitigated disaster. He scored just four league goals as Boro were relegated. Now plays in Qatar where he doubtless earns pot loads of cash.

Albert Luque

Deportivo La Coruna to Newcastle United; £9.5m, 2005

After three successful seasons at Deportivo La Coruna, Spanish international Luque arrived in Newcastle with quite the reputation as an attacking midfielder. Unfortunately, he was badly injured in his second game and from there he was career headed in one interminable direction. In two years at Newcastle he played just 21 times and it was no surprise when Sam Allardyce unloaded him in 2007. Worse was to follow, however: Luque now finds himself without a club.

Steve Marlet

Lyon to Fulham; £11.5m, 2001

The transfer that led to a court case. Marlet was a much coveted French international when he signed for Fulham in 2001. However, he was unable to replicate his form in west London and such was Fulham chairman Mohammed Al Fayed’s dissatisfaction with the transfer he took former Fulham manager Jean Tigana, who signed Marlet and had links to Lyon, to court, citing dubious overpayment. Although the case was soon dropped, it is obvious Fayed clearly paid over the odds for the ultimately mediocre Marlet. Not that we’re suggesting anything dodgy went on, mind.

Robbie Keane

Tottenham Hotspur to Liverpool; £20.3m, 2009

Let’s be clear, unlike some of the players on this hall of shame Robbie Keane is not a bad player. On his day – and that may have gone now – he’s a very, very good player. However, his ill-fated transfer to Liverpool in 2009 can only be described in the harshest of terms: a flop. Despite courting the player for months, Liverpool boss Rafa Benitez didn’t seem to know what to do with the Irish captain and after just six short months Keane found himself back at White Hart Lane. Strange, incredibly strange.

Joleon Lescott

Everton to Manchester City; £24m, 2009

We could, of course, fill a top ten with Manchester City flops from the last two years alone. Emmanuel Adebayor, Jo, Wayne Bridge, Roque Santa Cruz, even Robinho all failed to set Eastlands alight after big money transfers. And James Milner had better buck his ideas up too. However, we’ve gone for Lescott for sheer financial profligacy. Despite shining at Everton, he looks completely out of his depth at City. No worries, what’s £24 million to an oil-loaded Sheikh?

Gary Birtles

Nottingham Forest to Manchester United; £1.25m, 1980

Having won two European Cup winner’s medals under Brian Clough at Nottingham Forest, England forward Gary Birtles was meant to propel Manchester United to, what was by 1980, an elusive title. All his signature led to was the sack for the man who signed him, Dave Sexton. It took him 30 games to score for United and despite a slight improvement under Sexton’s successor Ron Atkinson, it was no surprise when he was shipped back to Nottingham. Still regarded as the worst transfer flop at Old Trafford.

Andriy Shevchenko

AC Milan to Chelsea; £30.8m; 2006

Arguably the finest striker in Europe during the first half of the 00s, Shevchenko was a fading force by 2006, as injuries and age began to take their toll. That didn’t stop Chelsea owner Roman Abramovich splashing out an incredible £30-odd million to secure his services in what turned out to be a vanity purchase. Jose Mourinho obviously didn’t fancy Shevchenko and he appeared only sporadically for the Blues as they relinquished the Premier League title to Manchester United. Eventually returned to Milan, but fared just as poorly there.

Steve Daley

Wolves to Manchester City; £1.4m, 1979

As much as we don’t want to heap further opprobrium upon Steve Daley – he’s only had 32 years of being labelled a misfit and the biggest waste of money in football history – he is clearly the transfer flop by which all transfer flops are judged. The transfer flop’s transfer flop if you will. A decent, hard-working player for Wolves, why Manchester City decided to spend an astronomical, for then, £1.4 million on him is still debated now. The fee weighed heavy on Daley and within two years he was gone. Thankfully he makes a living on the after-dinner speaking circuit taking the mickey out of the transfer, and, by extension, himself. Funny how City haven’t learned a thing about money not guaranteeing success.