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What a waste of money

A year on from the Fernando Torres and Andy Carroll deals, ESPNsoccernet puts together a selection of some of the other Premier League transfers that, for one reason or another, will be remembered for as dismal failures.

Marco Boogers (West Ham United, £800,000, 1995)

It was not a significant outlay in a summer that saw Stan Collymore join Liverpool for £8.5 million, and West Ham managing director Peter Storrie felt Boogers would have cost £3 million on the domestic market, but the signing of the 28-year-old striker from Sparta Rotterdam was a disaster from start to finish.

He complained when he was not named in the first-team line-up for the season opener against Leeds and, when brought on as a substitute at Manchester United four days later, was promptly sent off for a high challenge on Gary Neville. Boogers subsequently disappeared back to the Netherlands, and reports emerged suggesting he had declared himself "psychologically unfit for football", while a misheard conversation with West Ham's PA and travel arranger led The Sun to run a story entitled 'Barmy Boogers Living In A Caravan'.

Boogers issued an angry denial: "It is a complete lie. When I read that I was supposedly unwell in the head and living in a caravan, I thought there must be another Marco Boogers because it clearly wasn't me." Insisting he loved life in London, he agreed to return to England, but by September he had already been described as "the player who has caused me more problems in football than anyone else" by manager Harry Redknapp, who added: "All you can buy for that sort of money is someone who can tie their bootlaces, but this guy didn't even want to do that. He didn't like the way we trained. He didn't like anything. Now I can only hope to sell him back to a club in Holland."

Boogers made just two more substitute appearances before being offloaded back to Groningen on loan.

Tomas Brolin (Leeds United, £4.5 million, 1995)

Leeds' most expensive signing at the time - November 1995 - Brolin arrived from Parma amid significant fanfare after his displays for Sweden at the 1994 World Cup. If his name had carried weight before his arrival, though, his waist seemed to have taken the burden when he rocked up at Elland Road.

Manager Howard Wilkinson soon lost patience after a string of indolent displays, and when his successor, George Graham, named him on the bench for the League Cup final in March, Brolin made clear his desire to leave. Though his two-and-a-half-year deal included an end-of-season get-out clause, finding a suitor became more difficult when, in May, his surgeon announced that Brolin wouldn't be able to run properly for another three months after undergoing ankle surgery on an injury suffered 18 months earlier.

Loan spells with FC Zurich and Parma followed before Leeds, in October 1997, paid Brolin £140,000 to cancel his contract.

Winston Bogarde (Chelsea, free, 2000)

While no transfer fee was involved, Bogarde remains the definitive cautionary tale for clubs seeking a bargain. Having spent the previous six years with Ajax, AC Milan and Barcelona, and coming with the recommendation of compatriot Mario Melchiot, Bogarde - who had apparently been touted to Bradford just weeks earlier - described his move to Chelsea on a four-year contract as his "ultimate dream".

However, when he turned up for training a few days after signing, he learned that manager Gianluca Vialli had been fired, and swiftly fell out with his replacement, Claudio Ranieri, who relegated him to the reserves and eventually the youth team. Sitting on a £40,000-a-week contract, Bogarde steadfastly refused to consider Chelsea's attempts to negotiate a release and stayed put until the deal expired in the summer of 2004.

"Why should I throw €15 million away when it is already mine? At the moment I signed it was in fact my money, my contract," he explained in his autobiography. "Both sides agreed wholeheartedly. I could go elsewhere to play for less, but you have to understand my history to understand I would never do that. I used to be poor as a kid."

Francis Jeffers (Arsenal, £8 million, 2001)

When Patrick Vieira was making noises about leaving Arsenal in the summer of 2001, Arsene Wenger went on a spending spree to assuage his concerns over the squad. The first to arrive, for an initial £8 million, was 20-year-old Everton striker Jeffers, the 'fox in the box' Wenger had sought since the departure of Ian Wright three years earlier. "The best reassurance is to sign players like this," Wenger said. "I am still convinced Patrick will be an Arsenal player next season."

Jeffers suggested that he could become an "instant hero" should he follow in Wright's footsteps, but he was an abject failure. The injury problems apparent during the previous two seasons at Everton did not abate and, despite Arsenal winning the league in his first season, his seven appearances were insufficient to warrant a medal. He was not part of the matchday squad for the 2002 or 2003 FA Cup final victories and, after scoring only four league goals in two years, was loaned back to Everton for the 2003-04 campaign. Failing to add a league goal during his second spell at Goodison Park, he returned to Arsenal before being sold off to Charlton for £2.6 million in 2004.

Juan Sebastian Veron (Manchester United, £28.1 million, 2001)

Following an impressive five years in Italy with Sampdoria, Parma and Lazio, Sir Alex Ferguson broke the British transfer record to take Veron to Old Trafford in the summer of 2001, but his style was unsuited to the English game and, given the fee, questions were soon being raised. In May 2002, with Manchester United having failed to win any of the five competitions they entered that season, Ferguson exploded when journalists pointed the finger at Veron, ordering them to "get out" of the press conference as they were "f**king idiots". In November, when a shareholder labelled Veron a "carthorse" at the club's AGM, Ferguson similarly dismissed the accuser as an "idiot".

In the summer of 2003, Ferguson remained insistent the "marvellous" Veron would stay put but, when Chelsea's interest manifested itself in a bid rising to £15 million, the midfielder was informed his time was up. As Veron himself said: "Ferguson trusted me when I first arrived, but later on it seemed we didn't understand each other as well."

At Chelsea, Claudio Ranieri also failed to coax any sustained form from Veron and, after making only seven Premier League appearances in the 2003-04 campaign, he was allowed to depart on loan to Inter.

Bosko Balaban (Aston Villa, £6 million, 2001)

When Aston Villa boss John Gregory agreed to sign Croatia striker Bosko Balaban from Dinamo Zagreb for £6 million in August 2001, his legendary compatriot Davor Suker expected big things. "He'll be a star in the Premiership," he said.

As it transpired, the striker made just eight league appearances - all as a substitute - in the 2001-02 campaign, failing to score a goal in any competition for club or country, before being loaned back to Dinamo Zagreb. In December 2003, having returned and been banished from first-team training by manager David O'Leary, Villa paid £1 million to terminate his contract.

It was calculated in the Daily Express that the deal had cost the club a total of £9 million, or £37,190 for each of his 242 minutes of first-team action.

El Hadji Diouf (Liverpool, £10 million, 2002)

Having claimed the African player of the year award in both 2001 and 2002 and included in the All-Star Team for the 2002 World Cup after his performances for Senegal, Gerard Houllier was sufficiently convinced to sign Lens forward Diouf ahead of Nicolas Anelka, who had been on loan at Anfield.

Diouf's early career had been marked by a string of transgressions - most notably when he crashed his car while driving without a licence - but he said: "I learnt from my mistakes." How much he had learnt was open to debate, for it did not take long for controversy to arise at Liverpool. Having been accused of spitting at West Ham fans in November 2002 - though police said he merely spat on the ground - he was found guilty of spitting at a Celtic fan in a UEFA Cup quarter-final of March 2003, resulting in fines from his club and Glasgow Sheriff Court.

On the field, he was similarly disappointing: he scored six goals in 44 appearances in his first season, and in his second failed to find the net in 32 games. In May 2004, Houllier described Diouf as his most disappointing signing, adding: "On occasions he has not given a good impression of the club."

He was loaned to Bolton for the 2004-05 season, and did not return to Anfield.

Per Kroldrup (Everton, £5 million, 2005)

Having spent four years in Italy with Udinese, Everton shelled out £5 million to take Denmark international Kroldrup to Goodison Park in 2005. In August, before he could make his debut, he sustained a groin injury, and it was not until Boxing Day that he made his first-team debut. Everton lost 4-0 to Aston Villa that day, with the debutant variously described as "ill at ease" (The Independent), "off the pace" (Daily Star) and "like a rabbit in the headlights" (Liverpool Echo).

He was said to have damaged his ankle ligaments afterwards, and his only other appearance came as a substitute in a 1-0 FA Cup victory over Millwall. The following month he was offloaded to Fiorentina at a £2 million loss. "I don't really feel I have had the chance to prove my worth," Kroldrup said.

Andriy Shevchenko (Chelsea, £30.8 million, 2006)

After a seven-year spell with AC Milan in which he became the club's second highest scorer of all-time, Roman Abramovich sealed the marquee signing he had prized above all: Shevchenko joined Chelsea for a British record £30.8 million fee in 2006.

Despite a goal on his debut, it soon became clear that the Ukrainian was unsuited to his new club. By December, he had fallen out of the first-team reckoning, and Milan owner Silvio Berlusconi was mocking him at the club's Christmas party, labelling the striker his wife's "lapdog" for agreeing to the move. Shevchenko's second season with the Blues was curtailed by injury and, though he showed occasional glimpses of his quality, the spark of old had been extinguished by the time Luiz Felipe Scolari allowed him to return to Milan on loan for the 2008-09 season.

His second spell with the Rossoneri failed to bring a single goal in Serie A, and Milan announced that he would return to Chelsea at the end of the season. Carlo Ancelotti also headed to Stamford Bridge in the summer of 2009, but Chelsea released the 33-year-old from the final year of his £121,000-a-week contract to enable him to rejoin first club Dynamo Kiev. "Roman Abramovich and everyone at Chelsea have been very kind to me," he said.

Roque Santa Cruz (Manchester City, £17.5 million, 2009)

In his eight years at Bayern Munich, Santa Cruz had marked himself out as a talented but injury-prone bit-part player and, having scored only 31 goals in 146 appearances, he was allowed to leave for Blackburn for £3.5 million in July 2007. Towards the end of a successful debut season in which he netted 19 league goals, manager Mark Hughes was touting him, alongside Liverpool's Fernando Torres, as the signing of the summer, adding: "Pound-for-pound, I'm sure ours was the better buy."

Hughes would depart for Manchester City that summer and, despite Santa Cruz netting only four league goals for Rovers in the 2008-09 campaign, remained sufficiently enamoured to sanction a £17.5 million transfer for the Paraguayan at the end of the season. He opened his account in the Carling Cup against Scunthorpe at the end of October, but did not score again until his brace in the 4-3 victory over Sunderland on December 19.

By the time of those goals, Hughes had already been informed that he would be relieved of his managerial duties and, under Roberto Mancini over the following 12 months, Santa Cruz managed just one goal in all competitions. He was duly sent out on loan to Blackburn, where he failed to score in ten appearances, and is now with Real Betis, netting five times so far despite a near three-month goal drought.

Alberto Aquilani (Liverpool, £17 million, 2009)

If Rafael Benitez's biggest mistake as Liverpool manager was to alienate Xabi Alonso, the error was compounded in grand fashion when he invested €20 million in Aquilani. The Italy international had developed a reputation for injuries after making only 35 appearances for Roma in the previous two years, and he arrived at Anfield nursing an ankle injury. "We have to wait for a month for him to be fit, but he is a player we are signing for five years, not for five matches," Benitez explained.

Aquilani did not make his Premier League bow until November, by which time Liverpool had lost five of their opening 11 matches, with Steven Gerrard telling FourFourTwo that "it will take a while before Alonso's out of our system". By the time Aquilani made his first league start on Boxing Day, the club had won only two of the preceding seven games and, though there was an improvement in the second half of the season, Benitez was dismissed after the club finished seventh.

The summer allowed Aquilani to regain his fitness but, in August 2010, new manager Roy Hodgson let him join Juventus on a season-long loan. That deal was not made permanent but, when he returned, Kenny Dalglish approved a loan to AC Milan.

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