Having looked over 28 years of transfer data for my list of the 100 best Premier League transfers -- 100-51 here and 50-1 here -- it is time to go in the opposite direction. Say goodbye to Thierry Henry and hello to Bebe. It's time for the 50 worst transfers in Premier League history.
I tried to keep the rules for determining the worst transfer simple. In short, I wanted to measure the impact a player had on a club versus the impact he would have been expected to have when he signed originally. I paid special attention to anyone whose story or impact off the pitch was particularly notable. And while I considered only a player's performance as a Premier Leaguer in the best transfers piece, in this feature I factored in what he did after relegation if it continued to make the transfer look worse, most notably with anyone whose wages continued to drag down his team.
One more note: All the transfer values in this column are from Transfermarkt. Some of that data might be at odds with what was publicly reported at the time.
Honorable mentions
Eric Djemba-Djemba (Manchester United) is the patron saint of these sorts of lists, but I really think it's more about his name than anything else. The Cameroonian cost only £4.1 million when he was signed by United in 2003, and as a 22-year-old, he was more of a prospect than a realistic replacement for Roy Keane. If he were named Eric Stevens and arrived from Bradford City, Djemba-Djemba would not get the same sort of attention he has since leaving United.
Several strikers who flamed out in a short time span miss out, including Ricky van Wolfswinkel (Norwich City), Jozy Altidore (Sunderland) and Andreas Cornelius (Cardiff City).
I'm not quite prepared to rule on most of the transfer flops of the 2019-20 campaign given the unique position we find ourselves in because of the coronavirus outbreak, so Tanguy Ndombele (Tottenham) Joelinton (Newcastle) and Moise Kean (Everton) get a pass, at least for now.
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50. Marcelino, DF, Newcastle
Signed from Real Mallorca (Spain) for £6 million, 1999
At a time when English football was still relatively insular and distrustful of foreign players, Marcelino became the caricature of what could go wrong if a team dared look outside the British Isles for talent. The Spain international couldn't stay healthy early in his tenure on Tyneside, and after Ruud Gullit was sacked, Sir Bobby Robson simply didn't trust him.
Having developed a reputation as a "bottler," he spent four years with the club but played just 17 matches, including zero across his final two years in the Premier League. While Marcelino helped Rafa Benitez prepare for his time managing Newcastle and returned to watch his old team play, supporters still asked about the finger injury that cost the defender more than two months on the sideline.
49. Dennis Wise, MF, Leicester City
Signed from Chelsea for £3.2 million, 2001
Signed as a 35-year-old to replace Neil Lennon in midfield, Wise immediately presided over Leicester's relegation from the Premier League. He then showed up to training camp the next summer in Finland and punched teammate Callum Davidson in a card game spat, breaking the Scottish player's cheekbone. The punch cost Wise the £3m remaining on his Leicester deal and is likely the best thing he ever did for the club, which soon entered administration.
48. Park Chu-Young, FW, Arsenal
Signed from Monaco (France) for £5.9 million, 2011
The South Korea international was one of several signings Arsene Wenger seemed to make in a panic at the end of the 2011 summer transfer window, just days after his club had been ripped to shreds in an 8-2 defeat at Old Trafford.
While the club signed future manager Mikel Arteta and academy boss Per Mertesacker, they also added overmatched left-back Andre Santos and striker Park over the two-day span, with the latter leaving his hotel in the middle of a medical with French side Lille to sign for the Gunners. While Santos had his own issues, Park played a total of eight minutes in the Premier League over two-plus seasons with the club.
47. Milton Nunez, FW, Sunderland
Signed from PAOK Salonika (Greece) for £2.4 million, 2000
Also known as Tyson Nunez, the Honduran made just one substitute appearance during his time on Wearside, which is fitting for a player whom Sunderland signed by accident. Sunderland manager Peter Reid was reportedly attempting to sign 6-foot-0 future MetroStars striker Adolfo Valencia to his team, but he mistakenly ended up with 5-foot-4 Nunez instead.
The whole situation ended up in a lawsuit, although Nunez wasn't totally sidelined during his time with the Black Cats. He scored a brace in a 3-2 Honduras road win at RFK Stadium against the U.S., which was the last World Cup qualifier the U.S. lost on home soil for 15 years.
46. Yannick Bolasie, FW, Everton
Signed from Crystal Palace for £26 million, 2016
While Everton's recruitment in the Farhad Moshiri era has been inconsistent at best, few would have argued with the signing of the 27-year-old Bolasie from Crystal Palace when it happened. Sadly, the winger tore his ACL months after arriving and hasn't been the same player since.
The Congo international missed nearly a full year and has made just 29 appearances over four seasons at Everton, with the club loaning him to Aston Villa, Anderlecht and Sporting Lisbon. Bolasie, reportedly earning something close to £80,000-per-week, has produced more loans (three) than league goals (two) during his time at Goodison Park.
45. Angel Di Maria, FW, Manchester United
Signed from Real Madrid (Spain) for £67.5 million, 2014
One of the most significant examples of United's habit of getting the least out of world-class players, Di Maria got off to an impressive-enough start at Old Trafford after being signed for a British transfer record. The Argentine was named club Player of the Month in October but, after missing time with a hamstring injury, never seemed to regain his old form.
His family was understandably unsettled by an attempted robbery in February, while the star winger was scapegoated for Louis van Gaal's uninspiring debut season. He was sold to PSG after one season at a loss of £10.8m, at which point Di Maria returned to his old self.
44. Afonso Alves, FW, Middlesbrough
Signed from Heerenveen (Netherlands) for £15.3 million, 2008
Sometimes, you mine the Eredivisie for its top scorer and come away with Ruud van Nistelrooy. Other times, you end up with Alves, who had scored 44 goals in 39 matches for Heerenveen before joining Middlesbrough in the winter transfer window. He was actually decent in his first half-season with the club, scoring six goals in 651 minutes, but the subsequent year was a disaster.
In 2008-09, Alves scored just four times in 31 appearances for a Boro team that netted just 28 goals all season, the fewest of any Premier League club. Gareth Southgate's team unsurprisingly went down, with Alves taking much of the blame before leaving for Al-Sadd.
43. Per Kroldrup, DF, Everton
Signed from Udinese for £6.1 million, 2005
Few players have had briefer Premier League careers than the Denmark international, who joined high-flying Everton in summer 2005 and immediately suffered a groin injury. When he recovered, manager David Moyes inserted him into the lineup for a Boxing Day fixture against Aston Villa, which Everton lost 4-0.
After one January appearance as a sub in the FA Cup, Everton cut their losses and sold Kroldrup to Fiorentina for £3.6m. The 6-foot-4 defender had a fine career outside of England, but even he admitted he couldn't cope with English football.
42. Ben Gibson, CB, Burnley
Signed from Middlesbrough for £15.2 million, 2018
When Sean Dyche shelled out a club-record £15m to sign Gibson, Burnley thought they were signing an emerging central defender on the fringes of the England team. Over nearly two full seasons, though, Gibson has made a total of one Premier League appearance, scoring in a 5-1 defeat at the hands of Everton. He was last seen training with Middlesbrough and has likely completed his Clarets career.
41. Oumar Niasse, FW, Everton
Signed from Lokomotiv Moscow (Russia) for £16.1 million, 2016
Another recent Everton flop, Niasse has had a tenure with the club that has been downright bizarre. Signed by Roberto Martinez during the winter transfer window, Niasse played only 131 minutes over five matches before being told he had no future with the club by new boss Ronald Koeman.
After outlasting Koeman on Merseyside, Niasse became a bit of a cult hero and scored eight times in 22 appearances. Since then, though, he has played just 77 minutes over two seasons, mixing in a scoreless loan spell at Cardiff. His Everton career will end this summer.
40. Corrado Grabbi, FW, Blackburn
Signed from Ternana (Italy) for £10.2 million, 2001
With the days of Alan Shearer and Chris Sutton gone, you can understand why the recently promoted Rovers made their move to sign the 25-year-old Grabbi, who had finished second in Serie B after scoring 20 goals for lowly Ternana the prior season.
Graeme Souness was hoping to come away with a budding star, but Grabbi failed miserably in England and scored just once in his debut season, losing his place to Andy Cole. Grabbi finished his run in England with two Premier League goals in 950 minutes across three seasons before returning to his home country.
39. Fernando Torres, FW, Chelsea
Signed from Liverpool for £52.7 million, 2011
Most of the players on this list have not been up to the standards of the Premier League, but Torres is a different sort of problem. While he was one of the best strikers on the planet during his time at Atletico Madrid and Liverpool, he was surprisingly ordinary after signing for Chelsea.
Torres scored 65 league goals in 7,856 minutes for Liverpool, or about once every 120.8 minutes; after signing for Chelsea, he netted a mere 20 league goals in 6,824 minutes, which was closer to once every 341 minutes. He was 26 upon his arrival, so it wasn't as if Chelsea signed a player who should have been past his peak. It just never seemed to come together in West London for the World Cup winner, who scored just once in his first half-season and never topped eight Premier League goals in his time with the club.
Chelsea eventually let Torres, the most expensive player on this list, leave on a free transfer. His tenure didn't live up to expectations, but fans still have some fond memories of his time with the club, most notably his goal at Barcelona that sealed a place in the 2012 Champions League final.
38. Andy Carroll, FW, Liverpool
Signed from Newcastle United for £36.9 million, 2011
The player signed to replace Torres didn't turn out too well, either. There was understandable shock when Liverpool broke their club record for the second time in a matter of hours, but while the £22.8m move for Ajax's Luis Suarez turned out to be a work of genius, Carroll's signing proved to be a misstep.
The 22-year-old had really spent only one half-season as a starting striker for Newcastle in the top flight, scoring 11 goals in 19 games, but injuries and coaching changes marginalized the lanky striker. He scored just six goals in 44 matches for Liverpool before being shipped off to West Ham.
37. Juan Sebastian Veron, MF, Manchester United
Signed from Lazio (Italy) for £38.3 million, 2001
In hindsight, it does seem a little curious that Sir Alex Ferguson attempted to break up that famous midfield of Ryan Giggs, Roy Keane, Paul Scholes and David Beckham by making Veron the most expensive transfer in English history at the time. Veron was a more complete player than any of the four, but as Gary Neville said with the benefit of hindsight, he wasn't a like-for-like replacement for either of United's central midfielders.
Ferguson saw Veron as a unique difference-maker and famously defended the player in an expletive-filled rant to the media, but despite winning Player of the Month in his first full month with the club, Veron seemed to wither by the end of his first season and never seemed to find the right role with the club. United cut their losses after two years and sold him to Chelsea for £19.3m.
36. Andrea Silenzi, FW, Nottingham Forest
Signed from Torino (Italy) for an unknown fee, 1995
One of the top scorers in Serie A in 1994 and a one-time Italy international, Silenzi was unfairly positioned as the replacement for Stan Collymore, who had just been sold to Liverpool. Ostracized as the first Italian in Premier League history, Silenzi failed to score in 12 appearances, only three of which were starts. Forest then sent Silenzi back to Italy on a loan from which he never returned.
35. Didier Ndong, MF, Sunderland
Signed from Lorient (France) for £18 million, 2016
34. Papy Djilobodji, DF, Sunderland
Signed from Chelsea for £8.6 million, 2016
I'll link these two players because they both went through a similar saga. Sunderland signed Ndong and Djilobodji in summer 2016. Neither impressed as Sunderland finished with just 24 points and were relegated. Ndong was a much better player than Djilobodji, but both of their Stadium of Light careers ended the same way. They each went on loan during Sunderland's infamous follow-up season, when they were relegated for a second consecutive campaign. Both were released after failing to report for training over the summer, a tactic the club likely preferred to get their respective wages off the books.
33. Massimo Taibi, GK, Manchester United
Signed from Venezia (Italy) on a free transfer, 1999
Other sources have suggested Taibi cost £4.5m, but at any price, his brief run as United goalkeeper was a disaster. Ferguson signed Taibi to compete with Mark Bosnich and Raymond van der Gouw as the Scot tried to replace Peter Schmeichel. The Italian started only four matches for United, allowing 11 goals in the process, most notably that famous gaffe against Southampton's Matt Le Tissier.
That came in Taibi's third appearance, and while the 6-foot-3 keeper blamed his studs, there were no such excuses when Taibi allowed five goals against Chelsea in his fourth and final appearance for United. Ferguson's other keepers allowed only 34 goals across their other 34 games, though, as United comfortably won the league.
32. Francis Jeffers, FW, Arsenal
Signed from Everton for £13.8 million, 2001
Arguably the first significant transfer misfire of the Wenger era, the 20-year-old Jeffers was famously signed to serve as the "fox in the box" for an Arsenal team that had only the likes of Thierry Henry and Dennis Bergkamp to rely upon for scoring. Jeffers had some injury issues even before signing for the Gunners, but the reality is that he just wasn't a great player. He scored six Premier League goals in three consecutive seasons for Everton as a teenager, then never topped that mark in any season at any level afterward. He scored just four goals in 548 minutes for Arsenal before beginning the itinerant phase of his career.
31. Kostas Mitroglou, FW, Fulham
Signed from Olympiakos (Greece) for £13.7 million, 2014
With Fulham attempting to avoid relegation, the addition of Mitroglou seemed like a coup. The Greece international had scored 30 goals in his prior 36 appearances for Olympiakos, which led the Cottagers to shell out a club-record fee to sign him in January.
But if you don't remember Mitroglou's career at Craven Cottage, well, you aren't alone. Fulham sacked Rene Meulensteen and replaced him with Felix Magath, whose hyper-emphasis on fitness led the German to omit Mitroglou from the team. The striker played just 153 scoreless minutes for relegated Fulham and never appeared for the club again. He went back to Olympiakos on loan and then to Benfica before being sold to the Portuguese club for £6.3m in 2016.
30. Marco Boogers, FW, West Ham
Signed from Sparta (Holland) for £653,000, 1995
Things started bad and didn't get much better for Boogers, who was sent off in his second appearance for the Hammers after an attempt to saw off Gary Neville's leg at the knee. Boogers would make just two more appearances for West Ham and finished his Premier League career with 100 total minutes on the pitch.
When he returned to Netherlands during his four-game suspension for the Neville tackle, a misheard quote from West Ham's press officer led the Sun to publish a headline suggesting Boogers had left the club to live in a Dutch caravan. The story wasn't true, but, after a knee injury, he did return to his homeland to finish his career.
29. Nikola Zigic, FW, Birmingham City
Signed from Valencia (Spain) for £6.3 million, 2010
Six-foot-7 Zigic scored the opener in Birmingham's 2-1 Carling Cup final win over Arsenal, but the rest of his Birmingham tenure was less notable. He scored five goals in his first season as the club were relegated, and while he managed 28 goals over three years in the Championship, Birmingham simply couldn't get rid of the Serbia international.
Zigic was reportedly on £50,000-a-week and had no clause to reduce his wages in the case of relegation. With no takers, he lingered for years. It peaked with what manager Lee Clark called "the worst training session I have ever come across" in 2013.
28. Michael Owen, FW, Newcastle United
Signed from Real Madrid (Spain) for £22.5 million, 2005
You can't fault Newcastle for trying. With Alan Shearer entering his final year at the club, they tried to sign the best possible replacement for their club legend by bringing Owen back to England. Injuries had blunted his impact during a lone season in Madrid, but the pacey English star was still only 25 and had scored 70 goals across his final four seasons with Liverpool.
Everything went wrong for Owen during his first two seasons with the club, when he suffered thigh and foot injuries before tearing his ACL in the opening moments of England's 2006 World Cup game against Sweden. Owen played just 14 games over those first two years on Tyneside and, while the next two were better, he still managed only 19 league goals over 4,073 minutes and a total of 26 over his four years in black and white.
27. Owen Hargreaves, MF, Manchester United
Signed from Bayern Munich (Germany) for £22.5 million, 2007
While Hargreaves had battled injury issues before making his move to England in summer 2007, nobody could have anticipated just how badly the England international would fare in his struggle to stay healthy. Hargreaves won the double in his debut season for United, but his career was basically over at 27.
The Canada-born midfielder would make just five more appearances in the Premier League, four of which came over his final three seasons with United. After one subsequent 14-minute appearance for Manchester City, Hargreaves retired.
26. Seth Johnson, MF, Leeds United
Signed from Derby County for £10.4 million, 2001
Another English midfielder whose career was cut short in his 20s by injury, Johnson is most famous for the perhaps-apocryphal story surrounding his signing with Leeds. As it goes, Johnson arrived for his negotiations with Leeds chairman Peter Ridsdale hoping to come away with £13,000-per-week. Ridsdale's initial offer was £30,000-per-week, and when Johnson gasped, Ridsdale misconstrued the sentiment and upped his offer to £37,000-per-week. It became the perfect encapsulation of how Leeds' spending spree at the turn of the century went disastrously wrong.
Johnson struggled to stay healthy, and once the club entered administration and were relegated to the Championship, they were stuck in an impossible situation. He had made 59 appearances for the club, but with the 60th set to trigger a £250,000 payment to Derby that Leeds couldn't afford, Johnson sat on the bench for the remainder of the season. He would return to Derby on a free transfer, in part because he was impressed with the club's training facilities. They had been funded by Johnson's sale to Leeds.
25. Sergey Rebrov, FW, Tottenham
Signed from Dynamo Kyiv (Ukraine) for £16.2 million, 2000
Rebrov was part of a famous strike partnership with Andrey Shevchenko at Kyiv. While Shevchenko starred at Milan before disappointing at Chelsea, Rebrov went directly into the anonymous English phase of his career.
Spurs were hoping to see the striker who scored 10 times in the Champions League during his final season with Kyiv, but Rebrov managed just 10 Premier League goals over 59 appearances, including one in 30 during his second season. Spurs then loaned him to Fenerbahce for the remainder of his contract.
24. Roberto, GK, West Ham
Signed from Espanyol (Spain) on a free transfer, 2019
The only player signed in the present season on this list, Roberto's career with the Hammers was short but disastrous. Taking over for injured Lukasz Fabianski, calamitous performances saw Roberto allow 14 goals (including an own goal) across his seven starts. West Ham claimed just one point from those matches, and Roberto's struggles led the club to sack manager Manuel Pellegrini and director of football Mario Husillos.
The Hammers had a 31% chance of going down when the Premier League season was stalled and, given they were averaging 1.2 points per match without Roberto, it would be fair to pin a significant amount of blame on him if they do go down. Other players have cost more and failed to live up to much higher expectations, but very few players can inspire total regime change and open up the possibility of relegation in 686 minutes of football.
23. Giannelli Imbula, MF, Stoke City
Signed from Porto (Portugal) for £21.8 million, 2016
Stoke aren't the sort of club who would typically spend this much money on any one player, so there was a lot of pressure on club-record signing Imbula to make an immediate impact after Stoke signed him away from Porto. Charlie Adam compared Imbula to Patrick Vieira when he signed for the club in 2016, and given that Vieira was 40 years old at the time, it was probably fair.
Imbula became the symbol of Stoke's rapid decline and departure from the Premier League, as the midfielder made just 26 appearances over his two years with the club. He was dropped to the U-23 team and loaned out as Stoke were relegated. Imbula then helped Vallecano get relegated from La Liga before being sent home from his loan in Serie A with Lecce after three appearances. Stoke cancelled Imbula's contract by mutual consent with 18 months to go.
22. Saido Berahino, FW, Stoke City
Signed from West Bromwich Albion for £12.5 million, 2017
I would argue that once-promising Berahino did more to consign Stoke to the Championship. In 28 matches and 1,214 minutes for Stoke in the Premier League, he failed to score even once. After scoring three goals in the second tier the next season, the club terminated Berahino's contract after he was arrested on charges of driving drunk.
21. Eliaquim Mangala, DF, Manchester City
Signed from Porto (Portugal) for £40.5 million, 2014
Mangala looked to be a rising superstar when City spent more than £40m to buy him from Porto, but Mangala was inconsistent under Manuel Pellegrini and frozen out under Pep Guardiola.
The defender started just four more league matches under the former Barcelona manager and was loaned to Valencia and Everton. Mangala was allowed to leave for Valencia on a free transfer this summer and has the third-largest gap between his transfer fee and subsequent sale return of any player in Premier League history.
20. Jack Rodwell, MF, Sunderland
Signed from Manchester City for £11.3 million, 2014
It's unclear whether the one-time England international simply stalled after his rise at Everton or really wasn't all that good in the first place. Sunderland signed Rodwell after a two-year spell at Man City and gave him a contract worth £70,000-per-week, crucially leaving out a clause that would have reduced his salary if the Black Cats were relegated to the Championship. When Rodwell's indifferent play and struggles with injury helped push Sunderland into the second tier, they were stuck with one of the most expensive players in the division.
That would have been one thing if Rodwell were a key member of the club, but he played just 105 minutes as Sunderland were relegated again. Facing a £43,000-per-week salary in League 1, they were able to convince Rodwell to cancel his contract. He became the symbol of Sunderland's fall down the league as an overpaid, uninterested mistake. You can criticize him for taking the money, I suppose, but Sunderland are the ones who handed him the contract.
19. Agustin Delgado, FW, Southampton
Signed from Necaxa (Mexico) for £5.2 million, 2002
It should be telling that Southampton were more surprised when Delgado showed up in 2003 than they would have been if he had stayed home. Then one of the club's biggest signings, Delgado got on Gordon Strachan's bad side after seemingly prioritizing trips back to Ecuador for his national team over playing for the Saints.
He played just 65 minutes and trained five times in his first season after joining Southampton in 2002, only to then play all three matches for Ecuador in the World Cup. Delgado made just two starts and played a mere 303 minutes over his three years in England, scoring once. His time ended with Southampton threatening to block him from signing with another club until his contract expired, seemingly out of frustrated spite.
18. Kevin Davies, FW, Blackburn Rovers
Signed from Southampton for £10.1 million, 1998
Davies had a long, productive career and played more than 440 games in the Premier League, but very few of them came with Blackburn. Southampton paid just over £1m to sign Davies in 1997, but after a nine-goal campaign, Brian Kidd paid more than 10 times that amount to bring the 21-year-old to Blackburn, and then Davies scored one lone goal in his 21 appearances with the club. Blackburn were relegated, Kidd was fired and Davies was sent back to the Saints after the season in exchange for Egil Ostenstad.
17. Gaston Ramirez, AM, Southampton
Signed from Bologna (Italy) for £13.7 million, 2012
I promise this is the last Southampton attacker for a bit. Ramirez was signed as a 21-year-old out of Serie A and got off to a promising start in the Premier League, but after his first season, things went pear-shaped. The Uruguayan started just three matches and played a total of 578 minutes over his final three seasons on the south coast, contributing one goal and one assist over that timeframe.
Ramirez spent most of his time on the bench, although he did make loan moves to Hull City and then to Middlesbrough before heading to the Riverside on a free transfer. He was reportedly one of the club's highest earners at £65,000-per-week.
16. Alberto Aquilani, MF, Liverpool
Signed from Roma (Italy) for £18 million, 2009
Brought in as a replacement by Rafa Benitez for departing club legend Xabi Alonso, Aquilani failed to live up to his predecessor's established level of play. The Italian started just nine times in his lone season with Liverpool, and while Aquilani contributed five assists in 817 minutes, Benitez's departure brought Aquilani's career on Merseyside to a close.
He was loaned to Juventus and Milan before permanently joining Fiorentina for just £1.8m in 2012. Aquilani later said he wished he had never signed for Liverpool in the first place. You get the feeling their fans might agree.
15. Steve Marlet, FW, Fulham
Signed from Lyon (France) for £15.8 million, 2001
There are unquestionably worse players on this list, but I'm not sure any other Premier League signing led their chairman to take the manager who made the signing to court. Fulham owner Mohamed Al Fayed refused to pay sacked Jean Tigana part of his salary and accused the Frenchman of deliberately overpaying for Marlet to try to pocket part of the fee.
The move didn't work, but neither did Marlet, who scored 11 goals in 49 starts over his two seasons in West London. Marlet later described his time with the club as "hell".
14. Roger Johnson, CB, Wolves
Signed from Birmingham City for £7.2 million, 2011
When Wolves signed Johnson from relegated Birmingham, they were hoping to add a leader to their backline. The only place he led them was down the same path. With Johnson taking over as club captain, Wolves were immediately relegated.
The nadir of their season likely came when the defender was fined after showing up drunk for training in March, though there was further indignity when Wolves were relegated again the next year. Johnson never appeared for the club again.
13. David Bentley, MF, Tottenham Hotspur
Signed from Blackburn for £19.8 million, 2008
Spurs had every reason to be excited when they signed Bentley, an Arsenal prospect who left in search of first-team football before excelling at Blackburn. The winger arrived at Spurs as a 24-year-old who was breaking into the England team and left totally uninterested in football as a calling.
Bentley struggled in his debut season, contributing only one goal and three assists in 1,826 minutes, and things only got worse. After a second uninspiring season, he lost his place by dousing manager Harry Redknapp with a celebratory ice bucket. Spurs subsequently sent Bentley on loan to Birmingham, West Ham, Blackburn and even FC Rostov in Russia, without the winger showing his old form. Bentley was sidelined for months with a knee injury, and after his contract with Spurs expired, he chose to retire at the age of 29. He finished his Spurs career with just two goals and five assists in 42 appearances.
12. Bebe, MF, Manchester United
Signed from Vitoria Guimaraes (Portugal) for £7.9 million, 2010
If Bebe isn't the worst signing Sir Alex Ferguson made, he's certainly the most haphazard. Bebe hadn't played at a level beyond the Portuguese third division, but on the recommendation of former assistant Carlos Queiroz, Ferguson shelled out £7.9m to sign a player who once suited up for Portugal in the Homeless World Cup.
It was a bold move for a player Ferguson would later admit he had never seen play, with the Scottish legend claiming he had made the move to beat Real Madrid to the punch. He need not have bothered. Bebe suggested he would have preferred to stay at his orphanage, and while he later carved out a professional career in Spain, he wasn't up to the United standard. He played just 75 Premier League minutes during his time at Old Trafford.
11. Alexis Sanchez, FW, Manchester United
Signed from Arsenal in a swap for Henrikh Mkhitaryan, 2018
United's worst signing of the Premier League era, though, has to be this transfer that was seen as a coup at the time. Sanchez appeared set to join Manchester City before United's cross-town rivals balked at the Chilean star's wage demands. United handed Sanchez a four-and-a-half-year deal reportedly worth £391,000-per-week with £75,000 appearance bonuses and a £1.1m annual bonus in the hopes of the 28-year-old serving as the focal point of their post-Zlatan Ibrahimovic attack.
Instead, Sanchez scored just three Premier League goals in one-and-a-half seasons. While he has dealt with injuries, the reality is that the once-exciting winger has looked like a shadow of his old self. A slowed Sanchez doesn't fit in Ole Gunnar Solskjaer's counter-attacking style of play, and an attempt to reduce the wage bill led United to loan him to Inter this season. The Red Devils are still paying Sanchez more than £200,000-per-week to play in Italy.
United once signed Robin van Persie from Arsenal under similar circumstances and rode the star striker's goals to a league title. As great as that move was, the Sanchez transfer has gone equally as poorly.
10. Mario Balotelli, FW, Liverpool
Signed from AC Milan (Italy) for £18 million, 2014
Although it's easy to look back on Liverpool's first candidate to replace Suarez as a foolish bet, there was some logic behind their attempt. Balotelli was still only 24 and coming off of a 14-goal season in Serie A for Milan. The price was reasonable, and, in Brendan Rodgers, Liverpool felt they had a manager who had spent the past several seasons getting the most out of a mercurial talent in Suarez.
It quickly became clear that they had made a mistake. Rodgers was publicly critical in admitting Balotelli was his last available choice to replace Suarez, and the Italian scored one Premier League goal for Liverpool in 939 minutes before leaving to return to Milan on loan. His failure contributed to Rodgers' sacking just over a year after nearly leading Liverpool to a Premier League title. New boss Jurgen Klopp had little interest in Balotelli and allowed him to leave the club for Nice on a free transfer.
9. Winston Bogarde, DF, Chelsea
Signed from Barcelona (Spain) on a free transfer, 2000
Thanks to billionaire owner Roman Abramovich, it's been a long time since Chelsea had any meaningful financial concerns, but we're still not too far removed from the days when the club were deep in the red and on the verge of a financial crisis. Bogarde figured as one of the causes of their near-insolvency. He was signed on a free transfer and handed a contract worth £40,000-per-week under the stewardship of Gianluca Vialli, but things began to go wrong just 13 days later, when Vialli was sacked.
Replacement Claudio Ranieri didn't rate Bogarde, who began a lengthy run in the reserves. According to the man himself, Chelsea refused to loan him unless the other club would pick up the entirety of his wages. Naturally, nobody wanted to pay a defender short on match fitness and riding the Stamford Bridge bench £40,000-per-week, so Bogarde simply faded into the background. He made just nine Premier League appearances in his first season and then never made another for the club -- or any other side -- again.
8. Tomas Brolin, MF, Leeds United
Signed from Parma (Italy) for £4.5 million, 1995
While the media at the time seemed to blame Brolin's failures on his weight and lack of desire, I suspect some of the blame for this fiasco should fall on Leeds' shoulders. Brolin had suffered a serious foot injury on international duty for Sweden in 1994 and barely played for Parma before Leeds spent a club-record £4.5m to sign him in summer 1995.
Brolin actually wasn't all that bad in his brief time playing with the club, scoring four goals in 18 Premier League appearances, including a brace in a 2-0 win over West Ham. With Leeds manager Howard Wilkinson choosing to play Brolin out of position, the Swede decided to respond with a deliberately awful performance in a 5-0 loss to Liverpool the next week. Brolin refused to return to Leeds the next season, went to Zurich to play on a minimum salary to prove his point about money not mattering, and then briefly went back to Parma on a loan.
With the striker alternately practicing with the reserves or skipping out on training altogether, Leeds eventually banned him from their stadium during matchdays before releasing him altogether. After a brief spell with Crystal Palace, Brolin retired from the game at 28.
7. Andriy Shevchenko, FW, Chelsea
Signed from AC Milan (Italy) for £39.5 million, 2006
Thought of as Roman Abramovich's "white whale" for years, the Russian finally got his man and convinced Milan to sell Shevchenko to Chelsea for a British record fee. The move for the Ukrainian seemed likely to precede a move away for Didier Drogba, with Jose Mourinho expected to use Shevchenko as his preferred option up front. The problem was that the new man was 29 and, while he had been scoring for fun at Milan, he seemed to age overnight after his move to Stamford Bridge.
Injuries, inconsistency and the resurgent form of Drogba limited Shevchenko to just nine Premier League goals in 48 appearances. Mourinho stuck with Drogba and used Shevchenko out of position, leading Abramovich to eventually sack the Portuguese coach in 2007. Shevchenko went on loan to Milan after his second season and then moved back to Dynamo Kiev on a permanent transfer.
6. Dani Osvaldo, FW, Southampton
Signed from Roma (Italy) for £13.6 million, 2013
Osvaldo isn't the only Premier League player to get into a fight with a teammate -- John Hartson famously kicked Eyal Berkovic in the jaw while the two were at West Ham, and Kieron Dyer and Lee Bowyer got into a mid-match fistfight while the pair were at Newcastle -- but those were one-off incidents. Southampton had been forewarned and should have known better.
Osvaldo had already been sanctioned for fighting Erik Lamela at Roma before joining Southampton in 2013, and while he scored three goals in 855 Premier League minutes during the fall, Osvaldo's Saints career came to a close shortly after he head-butted defender Jose Fonte during training. Osvaldo never played for the club again, as he was loaned to Juventus, Inter, and Boca Juniors before being released.
5. Adrian Mutu, FW, Chelsea
Signed from Parma (Italy) for £17.1 million, 2003
One of the first signings of the Roman Abramovich era at Stamford Bridge, Mutu was expected to form an attacking partnership with fellow Serie A recruit Hernan Crespo. Mutu had a solid debut season at Chelsea, contributing six goals and eight assists in the 2003-04 campaign, but made just two appearances under Jose Mourinho before being released. The cause? A failed drugs test, with Mutu testing positive for cocaine usage.
Mutu was banned from the sport for seven months, with Chelsea releasing the forward before starting litigation against their former player. After various appeals, the courts ruled that he owed Chelsea around €17m from his own pocket.
4. Bosko Balaban, FW, Aston Villa
Signed from Dinamo Zagreb (Croatia) for £7 million, 2001
While £7m does not seem like an extravagant sum in the context of today's transfer values, consider that this was the 23rd-largest transfer in the summer of 2001 for a Premier League club. By that measure, it's roughly equivalent to Leicester paying £30.1m for Ayoze Perez last year. This was the sixth-largest fee Villa had ever paid for a player at the time, according to Transfermarkt's records. And, according to reports in 2002, most of the transfer fee ended up going directly to Balaban himself.
I want to put that in context because Balaban might be one of the least impactful signings in Premier League history. It took him eight months before he could complete a full 90-minute match, and even that came in the reserves. The Croatian never started, playing just 138 scoreless minutes across eight appearances, and was loaned back to Dinamo after a disastrous first season. After he threatened to spend the remaining 30 months of his contract in the reserves, Villa settled a deal to end his time in the Midlands after two years.
Balaban unsurprisingly blamed Villa for his failed tenure in England.
3. Ricky Alvarez, MF, Sunderland
Signed from Inter Milan (Italy) for £9.5 million, 2015
There's a lot to unpack here. Alvarez initially signed with the Black Cats on loan for £900,000 during the 2014 campaign. The loan had a clause obligating Sunderland to buy Alvarez at the end of the season as long as they stayed in the Premier League and a bothersome left knee didn't prevent Alvarez from passing a medical. Alvarez played just 13 games after suffering an injury to his right knee, which had undergone microfracture surgery years earlier. After staying up, Sunderland tried to get out of their obligation to buy, claiming that the right knee injury had been a product of the left knee troubles acknowledged in the original agreement.
Here's where it gets bad. Sunderland's attempt to get out of the agreement failed. At the same time, to reinforce their standing, the club didn't offer Alvarez a contract, which allowed the Argentinian to sign with Sampdoria on a free transfer. That's right: Sunderland paid £9.5m for a player who then immediately left the club.
It gets worse. Sunderland lost their claim that Inter should have repaid much of Alvarez's loan fee and wages as a result of the injury. Velez Sarsfield, which helped develop Alvarez earlier in his career, successfully sued to receive €362,500 in solidarity payments. On top of all that, Alvarez himself took Sunderland to the Court of Arbitration of Sport to sue the club for his loss of earnings between his time with Sunderland and Sampdoria. The Black Cats are suing their former club doctor for £13m to try to recoup losses. Given their success rate with litigation related to the Alvarez transfer, Sunderland might be smart to move on and pretend this never happened.
2. Danny Drinkwater, MF, Chelsea
Signed from Leicester City for £34.1 million, 2017
It's difficult to even remember now, but when Chelsea signed Drinkwater in summer 2017, he was still on the fringes of the England picture and a regular in midfield for Leicester. At the time, it seemed as if Chelsea might have signed him at the last moment after Ross Barkley turned down a move to Stamford Bridge -- Barkley would later head to Chelsea during the subsequent winter transfer window -- but, at the very least, they would have expected Drinkwater to be part of their midfield rotation, given he had been key to Leicester's incredible title win a year earlier.
Things obviously haven't panned out that way for the former Manchester United trainee. Drinkwater made 12 Premier League appearances in his debut season with Chelsea, but after Antonio Conte left, the midfielder has been floating out of relevance. There was one appearance under Maurizio Sarri in the Community Shield, and he has not appeared in a Chelsea kit since. Frank Lampard showed little interest in giving him an opportunity either, after arriving as his third manager in three seasons.
Loan moves to Burnley and Aston Villa have been more disastrous. After joining Burnley, Drinkwater got into a fight at a nightclub after allegedly trying to take home the girlfriend of League 2 defender Kgosi Ntlhe and suffering an ankle injury in the process. Drinkwater made only one appearance with Burnley, and while he made four with Villa, he was responsible for two goals in a 6-1 loss against Manchester City before being sent back to Chelsea after head-butting a teammate at training. With Drinkwater reportedly on £100,000-per-week, it's difficult to see how Chelsea will find a way out of their most disastrous signing.
1. Ali Dia, FW, Southampton
Signed on a free transfer, 1996
Other players have certainly been more damaging to their club's finances or performance than Dia, who signed for free and made only one appearance with Southampton. Nobody got sacked or relegated because of Dia, although you might argue that the former should have happened given the series of colossal missteps that led to him making his first and only Premier League appearance.
The Dia story feels as if it comes from another universe. A man calls Southampton manager Graeme Souness pretending to be World Player of the Year George Weah. The purported Milan striker recommends Dia, his cousin, suggesting he had just scored two goals for Senegal the prior week and had played with Weah for Paris Saint-Germain before spending 1995 in the German second division. He would be an exciting prospect if any of that had been true. Dia was actually a 31-year-old college student who occasionally dabbled in non-league football.
Souness brought Dia in on a trial. Days later, he named him to the bench for a Premier League match against Leeds. Amazingly, after an injury, Souness sent Dia on as a substitute in the 32nd minute for Matt Le Tissier. His Premier League career lasted 53 minutes before Souness admitted his mistake and substituted Dia off. Dia went back to non-league football, never to return.
From Southampton's perspective, this is the worst transfer in Premier League history. From a neutral side of things, this is one of the best things that has ever happened. I don't want to do the "in-my-day" argument because it's boring, but I think it's fair to suggest that the modern Premier League is staid and professional to a fault. Today, there's no way a random university student could get a Premier League manager on the phone, and even if they succeeded, it would take two seconds to realize none of those claims about Dia were true.
There's something romantic about getting on your landline and convincing one of the most decorated players in Liverpool history that your friend is a Premier League-caliber footballer, let alone actually getting him onto the pitch for 52 minutes. Dia spent nearly as much time on a Premier League pitch in 1996 as Drinkwater did for Burnley. There will always be more players who command disproportionate transfer fees or who struggle to stay healthy after making an expensive move. In the Premier League, there will never, ever be another Ali Dia.