In some ways, Premier League transfers are no different than buying and selling on the stock market. Regardless of the information managers have leading up to these transactions, some players simply don’t work out for clubs for one reason or another. Some struggle to adapt to life in England and to playing in the world’s most-watched league. Others are not good fits in squads even though the transfers made sense, on paper, at the time they were completed. Every Premier League team is responsible for flops and bad signings seemingly every year, whether those players arrive on a long-term basis or loans. That’s just the nature of the business.
The 20 clubs in the Premier League at the start of the 2018-19 campaign have all swung and missed in transfer windows during the 2000s. It should be pointed out that not every flop sunk a club into relegation or prevented a team from competing for a spot in European football or a trophy. Surviving a bad transfer or two is a must and something each club has to prepare itself for because it is inevitable that some noteworthy and expensive signing will not live up to expectations. Fans of clubs that are able to put these bad transfers in the past are now able to laugh about these signings. Unfortunately, not every supporter is so lucky.
20 Arsenal: Gervinho
As Ed Malyon of the Mirror wrote, Gervinho lashed out at Arsenal manager Arsene Wenger a little over a year after Wenger sold his former player to Roma. Arsenal supporters may feel similarly about the forward who, simply put, was never good enough to routinely start for a Premier League side that yearned to do more than merely qualify for the Champions League at the time. In total, Gervinho scored 11 goals for the Gunners during his two seasons with the club. That’s a poor return for somebody who reportedly cost £11 million in the summer of 2011. Arsenal fans will always be able to remember this surprising miss when thinking about his time with the club.
19 Bournemouth: Jordon Ibe
We still haven’t seen a lot of AFC Bournemouth in the top flight, which makes determining the club’s worst transfer since 2000 a bit of an ask. Attacking option Jordon Ibe tops the list, for now, largely because he has yet to show he was worth the reported transfer fee of £15 million. The 22-year-old who couldn’t find a home in the Liverpool team underwhelmed so much in the early stages of his stint with the club that manager Eddie Howe labeled the player “a disappointment,” as Paul MacInnes of The Guardian wrote. The club may look to sell Ibe during the summer if it can reclaim some of the money spent on him.
18 Brighton and Hove Albion: Kemy Agustien
Midfielder Kemy Agustien had years of experience playing in England underneath his belt when he signed for Brighton and Hove Albion in the summer of 2013. The club didn’t realize, at the time, it had acquired somebody who would be more of a spectator than a contributor. By the time Brighton allowed his contract to expire following the 2014-15 season, injuries had already damaged whatever was left of his career. In total, Agustien made 17 appearances for the club across two campaigns. He failed to tally a goal or an assist. It wouldn’t be much of a surprise if supporters forgot he featured for the club.
17 Burnley: Leon Cort
Burnley signed defender Leon Cort for a reported fee of £1.5 million in January 2010, and it didn’t take long for the club to realize that the center back who was 30 years old at the time was already past his prime. An injury was added to the insult of this transfer months later when Burnley was relegated from the Premier League. Per Sky Sports, Cort backed the Clarets to make a quick return to the EPL. He would have no role in the club’s pursuit of Premier League football. He joined Preston North End on loan during the following campaign, and Burnley terminated his contract in January 2012.
16 Cardiff City: Solomon Taiwo
Midfielder Solomon Taiwo joined Cardiff City in August 2009 as a promising prospect. By January 2010, however, the idea was for Cardiff to send him on loan to Colchester United, but the club had to change those plans after others in the team suffered injuries. It was reported in the summer of 2010 that Cardiff wanted to sell Taiwo to Norwich City but was unable to do so because he failed a medical. In total, he made nine appearances during the three seasons that the club had his rights. As Matthew Southcombe of Wales Online explained, some fans couldn’t help but laugh after Taiwo failed to impress during an appearance on Masterchef. Maybe chicken and pasta wasn’t the best choice.
15 Chelsea: Fernando Torres
All things being equal, Fernando Torres may be the most famous of the worst transfers completed since 2000. Chelsea infamously spent £50 million in January 2011 on the Liverpool striker who never came close to justifying that transfer fee even if he did score some goals in competitions that fans will fondly remember. By August 2014, however, both sides accepted that the time had come for them to move on. Torres joined AC Milan on loan that summer, and he ultimately returned to Atletico Madrid, his first club, where he had far more success than he ever enjoyed while with Chelsea. When most casual fans recall his time with Chelsea, they remember that stunning miss against Manchester United.
14 Crystal Palace: Emmanuel Adebayor
According to Alex Martin of the Daily Mail and Reuters, striker Emmanuel Adebayor referred to his signing for Crystal Palace in January 2016 as the “worst decision” of his career. While Adebayor scored for Palace in February of that year, he would not find the back of the net a single time the rest of the season. In total, he scored once across 15 appearances, and Palace understandably released him in June 2016. As Billy Meyers of 90Min wrote, Adebayor earned £100,000 per week while with Palace. Some have questioned Adebayor’s commitment to clubs throughout his career. Those “Lazybayor” jokes won’t remove any money that he earned over the years from his bank account.
13 Everton: Gylfi Sigurdsson
When Everton spent what could, in total, have been up to £45 million on attacking midfielder Gylfi Sigurdsson in the summer of 2017, the hope was that the former Tottenham Hotspur and Swansea player would help bring Champions League fixtures to Goodison Park. By October of that same year, however, Sigurdsson himself admitted that he had not lived up to expectations, as Paul Brown of the Daily Star wrote. Everton ultimately finished eighth in the league table, and it is believed that he will return to the club for another go. Unfortunately, things went from bad to worse for Sigurdsson during the 2018 World Cup when he missed a penalty while featuring for Iceland in a match against Nigeria.
12 Fulham: Kostas Mitroglou
In January 2016, Max Cohen of Cottagers Confidential referred to striker Kostas Mitroglou as the “worst transfer in Fulham history.” Fulham reportedly paid £12 million for Mitroglou in January 2014 in an attempt to avoid relegation and remain in the Premier League. It didn’t work, in part because Mitroglou hardly featured for the club. Mitroglou appeared in three matches for Fulham, one of which was the contest that guaranteed the club’s drop to the second division. He never scored once for Fulham. If that wasn’t bad enough for supporters, Mitroglou found his shooting boots during a loan stint at Olympiacos and, later, with Benfica. The 30-year-old currently features for Olympique de Marseille.
11 Huddersfield Town: Lukas Jutkiewicz
Everton striker Lukas Jutkiewicz could not secure first-team football with the club in February 2009, so he joined Huddersfield Town, in League One at the time, on a loan. This move did not benefit either player or club. Along with not hitting the back of the net, Jutkiewicz also angered some supporters with his attitude on the pitch, particularly when he threw a training top after he was taken off at halftime of a match. As Pete Barrow of The Huddersfield Daily Examiner wrote, Jutkiewicz later apologized for his actions, but that was not enough to save his stint with the club. He wasn’t missed after netting zero goals in a handful of appearances.
10 Leicester City: Kelechi Iheanacho
Kelechi Iheanacho will turn only 22-years-old this October, but it’s possible that he could be on the verge of flopping with a second EPL side. Iheanacho made the move from Manchester City to Leicester City for a reported £25 million fee in August 2017, but there were rumors in January 2018 that Leicester was already looking to unload the striker. No such transfer happened at that time, and Iheanacho did enjoy some better outings en route to scoring eight goals for the club before the end of the campaign. Iheanacho makes the list because of the price paid for him, but he still has a chance to redeem himself while he remains with Leicester.
9 Liverpool: Christian Benteke
There were some other obvious candidates — looking at you, Andy Carroll — but we went with Christian Benteke for multiple reasons. Liverpool reportedly paid £32.5 million in July 2015 for Benteke, a striker who didn’t seem like a good fit for the club at the time and who never earned the trust of manager Jurgen Klopp after Klopp replaced Brendan Rodgers in October of that same year. By the end of the season, Benteke had started in only 14 Premier League contests for the Reds, and the nine goals that he netted wasn’t enough for Klopp to keep him past the summer. That August, Benteke completed an anticipated move to Crystal Palace, where he found success during his first season.
8 Manchester City: Roque Santa Cruz
Back in the summer of 2017, Daniel Rouse of The Score listed Manchester City buying Roque Santa Cruz for £17.5 million in June 2009 as one of the worst transfers in the history of the Premier League. You’d have to look long to find the worst City signing, which is saying a lot considering the club acquired Emmanuel Adebayor one month after landing Santa Cruz. Then-manager Mark Hughes reportedly coveted Santa Cruz because the two worked together at Blackburn. Injuries prevented Santa Cruz from finding his old form with City, and he scored only four goals across 18 months with the club before he figuratively limped back to Blackburn on a loan.
7 Manchester United: Angel di Maria
Manchester United supporters would probably prefer to forget about most of Louis van Gaal’s stint as manager, including the purchase of Angel di Maria from Real Madrid for £59.7 million in the summer of 2014. Those quick to defend Di Maria suggested that Van Gaal played him out of position and did not use him properly, and there was little doubt the two were not on the same page when Di Maria did not board the team’s flight to the United States for a pre-season tour in July 2015. “I have heard he is not on the plane,” Van Gaal famously said about the man deemed by many to be the worst transfer of the 2014-15 season. Di Maria joined Paris Saint-Germain later that summer.
6 Newcastle United: Michael Owen
Jackie Smithfield of The Mag produced a timeline of Michael Owen’s stint with Newcastle United after he signed for a club record fee of £16 million. That piece only tells portions of the story. Along with missing far too much playing time because of injuries, there are also whispers and allegations that he was more concerned with landing his next contract than he was with helping Newcastle avoid relegation. The final salt poured into the wound was Owen not signing a new contract with Newcastle in December 2008, a decision that ensured the club would not receive any money if and when Owen departed on a free transfer. He appeared for Newcastle 71 times across four seasons.
5 Southampton: Guido Carrillo
In January 2018, Southampton signed striker Guido Carrillo from Monaco as part of what the BBC reported to be a club-record transfer worth £19 million. The team would have been better off putting that money in a bank and letting interest grow. Perhaps the Premier League was too big of a jump for Carrillo, or maybe he was the wrong player for the club’s system. Whatever the case, Carrillo failed to score in seven appearances for the Premier League outfit. Manager Mauricio Pellegrino, sacked by Southampton in March, acquired Carrillo on loan with Leganes in July 2018. The best Southampton will get from the original deal will be if the team recovers some of the fee spent on Carrillo in a future transfer.
4 Tottenham Hotspur: Moussa Sissoko
Tottenham Hotspur supporters probably still cannot fathom that the club reportedly spent £30 million on midfielder Moussa Sissoko in August 2016 after he impressed in that summer’s UEFA European Championship. They also don’t understand why manager Mauricio Pochettino repeatedly picked Sissoko as a substitute up through 2018 even though anybody who watched Spurs play could see he wasn’t a good fit. By all accounts, Sissoko worked hard behind the scenes and wanted to do right by his manager and for the club. It’s just not meant to be in this scenario. Tottenham is expected to sell Sissoko to the highest bidder, if one is found, before the end of September 2018, a transfer that would delight many within the team’s fan base.
3 Watford: Mario Suarez
Some footballers lose it quicker than others, and that may have been the case regarding midfielder Mario Suarez when he signed for Watford in January 2016. Suarez failed to shine during 17 appearances with the club, and he moved to Spain's Valencia on a loan the following summer. That season didn’t go much better for Suarez, who was listed by Goal.com in the La Liga “Worst Team of the Season.” In July 2017, Suarez joined Chinese club Guizhou Hengfeng Zhicheng FC in a transfer that could see him fade from the memories of fans and viewers who only follow the biggest European competitions in the world.
2 West Ham United: Alou Diarra
West Ham United have a history of signing strikers who struggle with scoring goals, but it’s a midfielder who makes the list this time around. The signing of Alou Diarra for a fee reported to be £2 million in August 2012 was praised as a good piece of business at the time, but a thigh strain that he suffered in September sidelined him after making only a couple of appearances. The following January, Diarra lashed out at the club, per Chris Davie of Goal.com, and he later claimed that his joining West Ham was “a deal between clubs, a deal between agents” and a “bad choice,” according to Jonathan Lines of Brace the Hammer.
1 Wolverhampton Wanderers: Stefan Maierhofer
BBC Sport reported that Wolverhampton Wanderers splashed £1.8 million for striker Stefan Maierhofer in August 2009, but he made next to no impact during his one season at the club. He scored once for Wolves until a hernia sidelined him, and manager Mick McCarthy did not offer Maierhofer a guaranteed spot in the squad once he was recovered from that setback. He joined Bristol City on an emergency loan in March, a decision that did little to advance his career in England. Following the conclusion of the 2009-10 season, McCarthy told Maierhofer the club would listen to offers for his services. He never featured for Wolverhampton again.