Marco Boogers Boogers came from Sparta Rotterdam in 1995, was sent off for trying to maim Gary Neville in his second match, and was hardly seen again. "I signed Boogers off a video," said the West Ham manager Harry Redknapp. "He was a good player but a nutter."Photograph: Action Images/Action ImagesAndriy Shevchenko With friends like these, who needs £30.8m flops? Bought by Chelsea in 2006, reportedly because he was Roman Abramovich's mate and favourite player, Shevchenko was a hopeless, hapless flop who scored just nine league goals for Chelsea before returning to Dynamo Kyiv on a free transfer last weekPhotograph: Clive Rose/Getty ImagesRobbie Keane He was supposed to be the new Kenny Dalglish when he joined Liverpool from Spurs for £19m in the summer of 2008, but Keane bore more resemblance to Kelly Dalglish during his short Anfield career. He lasted just six months, scoring seven goals in 28 games before being dumped back on Tottenham's doorstepPhotograph: Ryan Pierse/Getty Images
Jean-Alain Boumsong Newcastle manager Graeme Souness paid Rangers a staggering £8m for Boumsong, a France international centre-back who, it soon emerged, barely knew how to co-ordinate his movements never mind repel Premier League defences. He was sold to Juventus 18 months later for just over a third of the fee Newcastle paid for himPhotograph: John Peters/Man Utd via Getty ImagesEl-Hadji Diouf When he starred in the 2002 World Cup for Senegal, it seemed Liverpool had got a bargain in Diouf, for whom they paid Lens £10m. Reality soon bit in a very painful place: in 2003-04, Diouf became the first No9 in Liverpool's history to fail to score a single goal in a season. His personality didn't exactly redeem him either, and he was soon packed off to Bolton for an undisclosed feePhotograph: Michael Steele/Getty ImagesPer Kroldrup Having finished fourth in 2004-05, the Everton manager David Moyes treated himself to a £5m Denmark international centre-half. Sadly he very quickly decided Kroldrup wasn't up to it, and gave him just one game before selling him to FiorentinaPhotograph: Clive Mason/Getty ImagesAndrea Silenzi The first Italian to play in the Premier League, but not one who will be remembered fondly. Nottingham Forest paid £1.8m to Torino for Silenzi, who failed to score a league goal in two years at the club before being booted back to ItalyPhotograph: Peter Hatter/EMPICS SportFrancis Jeffers The fox in the box who was actually a complete donkey. Jeffers cost £8m in 2001 and will always go down as one of Arsène Wenger's worst signings. He was eventually sold to Charlton for £2.6m in 2004Photograph: Mark Thompson/Getty ImagesAde Akinbiyi There has been no greater talent-spotter than Peter Taylor. Sadly that's the late Peter Taylor, Brian Clough's right-hand man, whereas the Peter Taylor who managed Leicester spent £5m on Akinbiyi, a semi-prolific lower-league goalscorer but one who was painfully out of his depth at the highest level. He scored 11 goals in 58 league games for Leicester, all the while making a brick wall look like it had a cushioned first touch, and was nicknamed Ade AkinbadbuyiPhotograph: Mike Finn-Kelcey/Getty ImagesJuan Sebastian Veron The man who broke up the last great all-British-and-Irish midfield, a golden goose that gave out a Premier League title each year until Sir Alex Ferguson tampered with it and paid Lazio £28.1m for Veron, a brilliant talent but one palpably unsuited to Manchester United's style of play. After two years of telling anyone who doubted Veron that they were "idiots", Ferguson took a hit of around £14m and sold Veron to Chelsea, where he was just badPhotograph: Paul Barker/AFP/Getty ImagesMarcelino The only footballer who could injure himself blinking. Marcelino, a Spain international centre-back who cost Newcastle £6.7m from Mallorca in 1999, picked up every injury known to man - and a few more besides - in his time at St James' Park. He played just 20 games in three years before being releasedPhotograph: Stu Forster/Getty ImagesAdrian Mutu Not a bad buy per se, and he will have proved very good value for money if Chelsea ever get their £14m compensation from him, but having to sack a player for cocaine abuse was not exactly in the spangly brochure of New ChelseaPhotograph: Neal Simpson/EMPICS SportNicolas Medina Fools and their money were easily parted at the start of the millennium, when a climate of buy-now-pay-later prevailed and all manner of football managers were allowed to spend all manner of fees on all manner of filth. In 2001, Sunderland's Peter Reid spent £3.5m on Medina, a future Argentina international who did not play a single league game for the club in three years before having his contract cancelledPhotograph: John Walton/EMPICS SportMichael Ricketts There's that Dutch accent and that reign as England manager, but Steve McClaren's grandest folly will surely always be his decision to pay £3m for Bolton's Ricketts, who had long since shot whatever bolt he had. Ricketts scored four goals in 38 games and was given a free transfer within 18 monthsPhotograph: Laurence Griffiths/Getty ImagesBosko Balaban In 2001, the Aston Villa manager John Gregory spent £6m on Balaban, a player who didn't start a single league game in two-and-a-half years and was given a £1m pay-off when he left in 2004, announcing that "Villa is all bullshit". Gregory thought Balaban was the last piece of the jigsaw. He might well have been, but it was a completely different puzzle: Balaban was one of a number of signings around the period who were palpably not suited to the muck and bullets of English footballPhotograph: Matthew Ashton/EMPICS SportMassimo Taibi Four games, 10 goals. Yet even the bald statistics of Taibi's Manchester United career don't tell the full story, containing as it does one immense howler against Southampton and two pretty impressive ones against Liverpool and Chelsea. Sir Alex Ferguson, who paid £4.5m for Taibi from Venezia, pretended it never happened and sent Taibi back to Italy Photograph: Phil Noble/PA ArchiveSergei Rebrov Spurs paid £11m for Rebrov, one of Europe's hottest properties, in 2000 but he failed spectacularly. He scored only 16 goals in 76 games, including one in 31 league games in his second and final season at White Hart Lane, before being farmed out to FenerbahcePhotograph: Phil Cole/Getty ImagesSteve Marlet The man who cost more than £1m per goal. Marlet scored 11 in 54 Premier League games, having gone to Fulham from Lyon for £11.5m in 2001. He was so bad that Fulham's owner, Mohammed Al Fayed, took the then manager Jean Tigana to court, claiming he had overpayed for Marlet. Fayed, like Marlet, had no successPhotograph: Phil Cole/Getty ImagesWinston Bogarde The man who bathed in money. Bogarde picked up £40,000 a week plus bonuses from Chelsea between 2000 and 2004 despite playing only 11 games. The club had repeatedly tried to sell him, but his wage demands scuppered any movePhotograph: Tony O'Brien/Action ImagesTomas Brolin When he arrived at Leeds from Parma in 1995, for a fee of £4.5m, Brolin was a shadow of himself - or rather twice the shadow, having ballooned during a spell on the sidelines through injury. Though only 25, his career descended sharply: he played only 19 league games in two years at Leeds before being released, and retired at the age of 28Photograph: Clive Brunskill/Getty Images
Sign up to read this article
Read news from 100’s of titles, curated specifically for you.