Ranking the 50 worst Premier League transfers of all time

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I tried to stick to the rules to determine the worst simple transfer. In summary, he wanted to measure the impact a player had on a club versus the impact he was expected to have when he originally signed. I paid special attention to anyone whose history or impact off the field was particularly remarkable. And although I only considered the performance of a player like Premier Leaguer in the best transfer piece, in this characteristic, I took into account what he did after the descent if the transfer continued to worsen, especially with anyone whose wages continued to drop his team.

One more note: all transfer values ​​in this column are from Transfermarkt. Some of that data may disagree with what was publicly reported at the time.

Honorable mentions

• Eric Djemba-Djemba (Manchester United) is the patron saint of these kinds of lists, but I really think it’s more about his name than anything else. The Cameroonian only cost £ 4.1 million when he was signed by United in 2003, and when he was 22, he was more of a prospect than a realistic replacement for Roy Keane. If his name was Eric Stevens and he came from Bradford City, Djemba-Djemba would not receive the same kind of attention since leaving United.

• Several strikers who caught fire in a short period of time are lost, including Ricky van Wolfswinkel (Norwich City), Jozy Altidore (Sunderland) and Andreas Cornelius (Cardiff City).

• I am not fully prepared to decide on most of the transfer failures of the 2019-20 campaign given the unique position we are in due to the coronavirus outbreak, so Tanguy Ndombele (Tottenham) Joelinton (Newcastle) and Moise Kean (Everton) get a pass, at least for now.

50. Marcelino, DF, Newcastle

Signed at Real Mallorca (Spain) for £ 6 million, 1999

At a time when English football was still relatively insular and suspicious of foreign players, Marcellin became the caricature of what could go wrong if a team dared to search for talent outside the British Isles. The Spain international was unable to stay healthy early in his Tyneside tenure, and after Ruud Gullit was fired, Sir Bobby Robson simply did not trust him.

Having developed a reputation as a “bottler”, he spent four years with the club but played only 17 games, including zero in his last two years in the Premier League. While Marcelino helped Rafa Benítez prepare for the time that Newcastle managed and returned to see his old team play, fans still asked him about the finger injury that cost the defender more than two months on the sidelines.

49. Dennis Wise, MF, Leicester City

Signed by 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 for training camp the following summer in Finland and hit his teammate Callum Davidson in a card game dispute, breaking the Scottish player’s cheekbone. The blow cost Wise the remaining £ 3m on his contract with Leicester and is likely the best he has ever done for the club, which soon entered administration.

48. Park Chu-Young, FW, Arsenal

Signed from Monaco (France) for £ 5.9 million, 2011

The South Korean international was one of many signings that Arsene Wenger seemed to panic at the end of the 2011 summer transfer window, just days after his club fell apart in an 8-2 loss at Old Trafford. .

While the club signed future manager Mikel Arteta and academy boss Per Mertesacker, they also added left back Andre Santos and forward Park within two days, with the latter leaving his hotel in the midst of a doctor with the French team Lille to sign for the gunners. While Santos had his own problems, Park played a total of eight minutes in the Premier League for more than two seasons with the club.

47. Milton Nunez, FW, Sunderland

Signed by PAOK Salonika (Greece) for £ 2.4 million, 2000

Also known as Tyson Núñez, the Honduran made a single substitute appearance during his time at Wearside, which is fitting for a player Sunderland signed by accident. Sunderland manager Peter Reid was reportedly trying to sign future MetroStars 6-foot 0 forward Adolfo Valencia into his team, but mistakenly ended up with Núñez 5-foot-4.

The entire situation ended in a lawsuit, although Núñez was not totally set apart during his time with the Black Cats. He scored a parenthesis in a 3-2 win at Honduras at RFK Stadium against USA. USA, which was the last World Cup qualifier that the USA USA He lost in his homeland for 15 years.

46. ​​Yannick Bolasie, FW, Everton

Signed by Crystal Palace for £ 26 million, 2016

While Everton’s recruitment into the Farhad Moshiri era has been inconsistent at best, few would have argued with Bolasie’s 27-year-old signing of Crystal Palace when it happened. Sadly, the winger broke his ACL months after arriving and has not been the same player since.

The Congo international missed almost a full year and has made just 29 appearances in four seasons at Everton, and the club loaned it to Aston Villa, Anderlecht and Sporting Lisbon. Bolasie, who reportedly earns 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 making the most of world-class players, Di Maria got off to a rather impressive start at Old Trafford after signing a British transfer record. The Argentine was named the club’s Player of the Month in October, but after wasting time with a hamstring injury, he never seemed to regain his former form.

44. Afonso Alves, FW, Middlesbrough

Signed in Heerenveen, The Netherlands for £ 15.3 million, 2008

Sometimes you extract the Eriedivisie for its top scorer and date Ruud van Nistelrooy. Other times, you wind up with Alves, who had scored 44 goals in 39 games 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 following year it was a disaster.

In 2008-09, Alves scored just four times in 31 appearances for a Boro team that scored just 28 goals in the entire season, the least number of Premier League clubs. As expected, Gareth Southgate’s team fell, and Alves took much of the blame before leaving for Al-Sadd.

43. By Kroldrup, DF, Everton

Signed by Udinese for £ 6.1 million, 2005

Few players have had shorter Premier League careers than the Denmark international, who joined Everton in the summer of 2005 and immediately suffered a groin injury. When he recovered, manager David Moyes inserted him into the lineup for a Boxing Day match against Aston Villa, which Everton lost 4-0.

After an appearance in the FA Cup in January, Everton reduced his losses and sold Kroldup to Fiorentina for £ 3.6 million. The 6-foot-4-foot defender had a good run outside of England, but even he admitted he couldn’t cope with English football.

42. Ben Gibson, CB, Burnley

Signed in Middlesbrough for £ 15.2 million, 2018

When Sean Dyche disbursed a club record of £ 15 million to sign Gibson, Burnley thought they were signing an emerging center defender on the sidelines of the England team. However, for nearly two full seasons, Gibson has made a total of one Premier League appearance, scoring a 5-1 loss at the hands of Everton. He was last seen training with Middlesbrough and has probably completed his career at Clarets.

41. Oumar Niasse, FW, Everton

Signed in Lokomotiv Moscow (Russia) for £ 16.1 million, 2016

Another recent Everton failure, Niasse’s tenure at the club has been downright bizarre. Signed by Roberto Martínez during the winter transfer window, Niasse only played 131 minutes in five games before new boss Ronald Koeman told him he had no future with the club.

After surviving Koeman in Merseyside, Niasse became a cult hero and scored eight times in 22 appearances. Since then, however, he has played just 77 minutes in two seasons, mingling a period of scoreless borrowing in Cardiff. His career at Everton will end this summer.

40. Corrado Grabbi, FW, Blackburn

Signed in Ternana (Italy) for £ 10.2 million, 2001

With the Alan Shearer and Chris Sutton days gone, you can understand why the recently promoted Rovers moved to sign the 25-year-old Grabbi, who had finished second in Serie B after scoring 20 goals for the humble Ternana last season. .

Graeme Souness hoped to date a budding star, but Grabbi failed miserably in England and scored just once in her debut season, losing her place to Andy Cole. Grabbi ended his career in England with two Premier League goals in 950 minutes in three seasons before returning to his home country.

39. Fernando Torres, FW, Chelsea

Signed in Liverpool for £ 52.7 million, 2011

Most of the players on this list have not lived up to Premier League standards, but Torres is a different problem. Although he was one of the best strikers on the planet during his time at Atlético Madrid and Liverpool, he was surprisingly normal after signing for Chelsea.

Torres scored 65 league goals in 7,856 minutes for Liverpool, or approximately once every 120.8 minutes; After signing for Chelsea, he scored just 20 league goals in 6,824 minutes, which was closer to once every 341 minutes. He was 26 upon arrival, so it wasn’t as if Chelsea had signed a player who should have passed his peak. He simply never seemed to team up in West London for the World Cup winner, who scored only once in his first half season and never surpassed eight Premier League goals in his time with the club.

38. Andy Carroll, FW, Liverpool

Signed at Newcastle United for £ 36.9 million, 2011

The player who signed to replace Torres didn’t turn out too well, either. There was an understandable shock when Liverpool broke their club record for the second time in a matter of hours, but while the £ 22.8 million move for Luis Suarez from Ajax turned out to be a brilliant job, Carroll’s signing turned out to be a step in false.

The 22-year-old really had only spent a half season as a starting striker for Newcastle in the top flight, scoring 11 goals in 19 games, but injuries and coach changes sidelined the lanky striker. He scored just six goals in 44 games for Liverpool before being sent to West Ham.

37. Juan Sebastián Verón, MF, Manchester United

Signed from Lazio (Italy) for £ 38.3 million, 2001

In hindsight, it seems a little curious that Sir Alex Ferguson has tried to break that famous midfield by Ryan Giggs, Roy Keane, Paul Scholes and David Beckham by making Veron the most expensive transfer in England’s 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 was not a similar replacement for any of United’s central midfielders.

Ferguson saw Veron as a unique marker of differences and defended the player in an outrageous protest to the media, but despite winning Player of the Month in his first full month with the club, Veron seemed to wither at the end of his first season and never seemed to find the right role with the club. United cut its losses after two years and sold it to Chelsea for £ 19.3 million.

36. Andrea Silenzi, FW, Nottingham Forest

Signed in Torino (Italy) for an unknown fee, 1995

Silenzi, one of Serie A’s top scorers in 1994 and once Italy’s international, unfairly positioned himself 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, of which only three were starts. Forest then sent Silenzi back to Italy on a loan from which he never returned.

35. Didier Ndong, MF, Sunderland

Signed in Lorient (France) for £ 18 million, 2016

34. Papy Djilobodji, DF, Sunderland

Signed by Chelsea for £ 8.6 million, 2016

I’m going to link these two players because they both went through a similar saga. Sunderland signed Ndong and Djilobodji in the summer of 2016. Neither of them impressed, as Sunderland finished with just 24 points and was relegated. Ndong was a much better player than Djilobodji, but his two careers at the Stadium of Light ended the same way. Each was loaned during Sunderland’s infamous follow-up season, when they were relegated for the second consecutive season. Both were released after failing to show up for training over the summer, a tactic the club probably preferred to take their respective salaries from their books.

33. Massimo Taibi, GK, Manchester United

Signed from Venice (Italy) in a free transfer, 1999

Other sources have suggested that Taibi cost £ 4.5 million, but at any cost, his brief career as a United goalkeeper was a disaster. Ferguson signed Taibi to compete with Mark Bosnich and Raymond van der Gouw when the Scotsman attempted to replace Peter Schmeichel. The Italian only started four games for United, allowing 11 goals in the process, most notably that famous gaffe against Matt Le Tissier of Southampton.

That came in Taibi’s third appearance, and while the 6-foot-3 goalkeeper blamed his tackles, there were no such excuses when Taibi allowed five goals against Chelsea in his fourth and final appearance for United. However, Ferguson’s other goalkeepers only allowed 34 goals in their other 34 games, as United comfortably won the league.

32. Francis Jeffers, FW, Arsenal

Signed by Everton for £ 13.8 million, 2001

Possibly the first major transfer flaw of the Wenger era, the 20-year-old Jeffers was signed to serve as the “fox in the box” for an Arsenal team that only Thierry Henry and Dennis Bergkamp could trust. punctuation. Jeffers had some injury problems even before signing for the Gunners, but the reality is, he just wasn’t a great player. He scored six Premier League goals in three consecutive seasons for Everton as a teenager and then never surpassed that mark in any season at any later level. He scored just four goals in 548 minutes for Arsenal before beginning the roving phase of his career.

31. Kostas Mitroglou, FW, Fulham

Signed in Olympiakos (Greece) for £ 13.7 million, 2014

With Fulham trying to avoid relegation, the addition of Mitroglou seemed like a coup. The Greece international had scored 30 goals in his 36 previous appearances for Olympiakos, prompting the Cottagers to pay a record club fee to sign him in January.

But if you don’t remember Mitroglou’s career at Craven Cottage, well, you’re not alone. Fulham fired 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 goalless minutes to relegate Fulham and never reappeared for the club. He returned to Olympiakos on loan and then to Benfica before being sold to the Portuguese club for £ 6.3 million in 2016.

30. Marco Boogers, FW, West Ham

Signed in Sparta (Netherlands) for £ 653,000, 1995

When he returned to the Netherlands during his four-game suspension for the Neville tackle, a misheard quote from the West Ham press officer led the Sun to publish a headline suggesting Boogers had left the club to live in a Dutch caravan. The story was not true but, after a knee injury, he returned to his homeland to finish his career.

29. Nikola Zigic, FW, Birmingham City

Signed from Valencia (Spain) for £ 6.3 million, 2010

The 6-foot-7-inch Zigic scored the first match in Birmingham’s 2-1 Carling Cup final victory over Arsenal, but the rest of his tenure in Birmingham was less noticeable. He scored five goals in his first season when the club was relegated, and although he had 28 goals over three years in the Championship, Birmingham simply couldn’t get rid of the Serbia international.

Zigic reportedly earned £ 50,000 a week and had no clause to reduce his wages in the event of a drop. Without takers, it lingered for years. It peaked with what manager Lee Clark called “the worst training session I’ve ever known” in 2013.

28. Michael Owen, FW, Newcastle United

Signed at Real Madrid (Spain) for £ 22.5 million, 2005

You can’t blame Newcastle for trying. With Alan Shearer entering his final year at the club, they attempted to sign the best possible replacement for their club legend by bringing Owen back to England. Injuries had cushioned his impact during a lonely season in Madrid, but the English star, who was still slow, was only 25 years old and had scored 70 goals in his last four seasons with Liverpool.

It all went wrong for Owen during his first two seasons with the club, when he suffered thigh and foot injuries before breaking his ACL in the opening moments of England’s 2006 World Cup match against Sweden. Owen played just 14 games during the first two years at Tyneside, and while the next two were better, he only managed 19 league goals in 4,073 minutes and a total of 26 in his four years in black and white.

27. Owen Hargreaves, MF, Manchester United

Signed by Bayern Munich (Germany) for £ 22.5 million, 2007

While Hargreaves had struggled with injury problems before moving to England in the summer of 2007, no one could have anticipated how badly the England international would fight to stay healthy. Hargreaves earned double in his debut season for United, but his career had basically ended at 27.

The Canadian-born midfielder would make just five more Premier League appearances, four of which came in his past three seasons with United. After a subsequent 14-minute appearance for Manchester City, Hargreaves retired.

26. Seth Johnson, MF, Leeds United

Signed in Derby County for £ 10.4 million, 2001

Another English midfielder whose career was cut short in his 20s due to injury, Johnson is famous for the perhaps apocryphal story surrounding his signing with Leeds. As he progresses, Johnson arrived for his negotiations with Leeds President Peter Ridsdale, hoping to get £ 13,000 a week. Ridsdale’s initial offer was £ 30,000 per week, and when Johnson gasped, Ridsdale misinterpreted the sentiment and increased his offer to £ 37,000 per week. It became the perfect encapsulation of how Leeds’ wave of spending at the turn of the century went disastrously wrong.

Johnson struggled to stay healthy, and once the club entered the administration and was relegated to the Championship, they were caught in an impossible situation. He had made 59 appearances for the club, but with the 60th set to provoke a £ 250,000 payment to Derby that Leeds could not afford, Johnson sat on the bench for the remainder of the season. I would return to Derby on a free transfer, in part because I was impressed with the club’s training facilities. They had been financed by the sale of Johnson to Leeds.

25. Sergey Rebrov, FW, Tottenham

Signed by Dynamo Kyiv (Ukraine) for £ 16.2 million, 2000

Rebrov was part of a famous strike association with Andrey Shevchenko in Kiev. While Shevchenko starred in Milan before disappointing Chelsea, Rebrov entered directly into the anonymous phase of his English career.

The Spurs expected to see the striker who scored 10 times in the Champions League during his last season with Kiev, but Rebrov scored just 10 Premier League goals in 59 appearances, including one in 30 during his second season. Spurs then loaned it to Fenerbahce for the remainder of his contract.

24. Roberto, GK, West Ham

Signed from Espanyol (Spain) in a free transfer, 2019

The Hammers had a 31% chance of falling when the Premier League season stalled, and since they were averaging 1.2 points per game without Roberto, it would be fair to put a lot of blame on him if they fall. Other players have cost more and have not lived up to much higher expectations, but very few players can inspire a complete regime change and open 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 is not the type of club that would generally spend that much money on any player, so there was a lot of pressure on club signing the Imbula record to have an immediate impact after Stoke booked him away from Porto. Charlie Adam compared Imbula to Patrick Vieira when he signed for the club in 2016, and since Vieira was 40 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 only 26 appearances during his two years at the club. They dropped it to the U-23 team and loaned it when Stoke was relegated. Imbula then helped Vallecano be relegated from La Liga before being sent home on his Serie A loan with Lecce after three appearances. Stoke canceled Imbula’s contract by mutual consent with 18 months to go.

22. Saido Berahino, FW, Stoke City

Signed by West Bromwich Albion for £ 12.5 million, 2017

I would say that the once-promising Berahino did more to consign Stoke to the Championship. In 28 games and 1,214 minutes for Stoke in the Premier League, he failed to score even once. After scoring three second-tier goals the following season, the club terminated Berahino’s contract after he was arrested for drunk driving.

21. Eliaquim Mangala, DF, Manchester City

Signed from Porto (Portugal) for £ 40.5 million, 2014

Mangala appeared to be a rising superstar when City spent over £ 40 million to buy it in Porto, but Mangala was inconsistent with Manuel Pellegrini and froze with Pep Guardiola.

The defender started just four more league games under the former Barcelona coach and was loaned to Valencia and Everton. Mangala was allowed to go to Valencia on a free transfer this summer and has the third-biggest gap between his transfer fee and the subsequent return on sale 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 stopped after his promotion to Everton or whether it really wasn’t that good in the first place. Sunderland signed Rodwell after a two-year stint in Man City and gave him a contract worth £ 70,000 per week, leaving out a clause that would have cut his salary if the Black Cats were relegated to the Championship. When Rodwell’s indifferent play and injury struggles helped push Sunderland to the second level, they got caught up with one of the division’s most expensive players.

19. Agustín Delgado, FW, Southampton

Signed in Necaxa (Mexico) for £ 5.2 million, 2002

It should be revealing that Southampton was more surprised when Delgado appeared in 2003 than he would have been if he had stayed home. Then, one of the club’s biggest signings, Delgado got on the wrong side of Gordon Strachan after apparently prioritizing return trips to Ecuador for his national team rather than 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 games for Ecuador at the World Cup. Delgado made just two starts and played a mere 303 minutes during his three years in England, scoring once. His time ended with Southampton threatening to block him from signing with another club until his contract expires, apparently out of frustrated rancor.

18. Kevin Davies, FW, Blackburn Rovers

Signed in Southampton for £ 10.1 million, 1998

Davies had a long and productive career and played more than 440 games in the Premier League, but very few of them came with Blackburn. Southampton paid just over £ 1 million 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, but Davies scored a lone goal in His 21 appearances with the Blackburn club 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 in Bologna (Italy) for £ 13.7 million, 2012

I promise this is Southampton’s last attacker for a while. Ramírez signed on as a 21-year-old Serie A player and had a promising start in the Premier League, but after his first season things turned pear. The Uruguayan started just three games and played a total of 578 minutes in his last three seasons on the south coast, contributing one goal and one assist during that period.

Ramirez spent most of his time at the bank, though he made loan moves to Hull City and then to Middlesbrough before heading to Riverside on a free transfer. He was reportedly one of the top earners at the club at £ 65,000 per week.

16. Alberto Aquilani, MF, Liverpool

Firmado en Roma (Italia) por £ 18 millones, 2009

Traído como reemplazo por Rafa Benítez para la leyenda del club que se marcha, Xabi Alonso, Aquilani no pudo cumplir con el nivel de juego establecido de su predecesor. El italiano comenzó solo nueve veces en su única temporada con el Liverpool, y aunque contribuyó con cinco asistencias en 817 minutos, la partida de Benítez puso fin a la carrera de Aquilani en Merseyside.

15. Steve Marlet, FW, Fulham

Firmado en Lyon (Francia) por £ 15.8 millones, 2001

Sin duda, hay jugadores peores en esta lista, pero no estoy seguro de que cualquier otra firma de la Premier League haya llevado a su presidente a llevar al gerente que hizo la firma a la corte. El propietario de Fulham, Mohamed Al Fayed, se negó a pagarle a Jean Tigana el saqueo de su salario y acusó al francés de pagar de manera deliberada para que Marlet intentara pagar una parte de la tarifa.

La jugada no funcionó, pero tampoco Marlet, quien anotó 11 goles en 49 aperturas durante sus dos temporadas en el oeste de Londres. Marlet más tarde describió su tiempo con el club como “infierno”.

14. Roger Johnson, CB, Lobos

Firmado desde la ciudad de Birmingham por £ 7.2 millones, 2011

Cuando los Lobos firmaron a Johnson desde Birmingham relegado, esperaban agregar un líder a su línea de fondo. El único lugar al que los condujo fue por el mismo camino. Con Johnson asumiendo como capitán del club, los Lobos fueron relegados inmediatamente.

El punto más bajo de su temporada probablemente llegó cuando el defensor fue multado después de aparecer borracho para entrenar en marzo, aunque hubo más indignidad cuando los Lobos fueron relegados nuevamente al año siguiente. Johnson nunca volvió a aparecer para el club.

13. David Bentley, MF, Tottenham Hotspur

Firmado en Blackburn por £ 19.8 millones, 2008

Un prospecto del Arsenal que se fue en busca del fútbol del primer equipo antes de sobresalir en Blackburn, los Spurs tenían todas las razones para estar emocionados cuando firmaron a Bentley. El extremo llegó a los Spurs como un jugador de 24 años que estaba ingresando al equipo de Inglaterra y se fue totalmente desinteresado en el fútbol como una vocación.

Bentley tuvo problemas en su temporada de debut, solo contribuyó con un gol y tres asistencias en 1,826 minutos, y las cosas solo empeoraron. Después de una segunda temporada poco inspiradora, perdió su lugar al rociar al gerente Harry Redknapp con un cubo de hielo de celebración. Posteriormente, Spurs envió a Bentley en préstamo a Birmingham, West Ham, Blackburn e incluso al FC Rostov en Rusia, sin que el extremo mostrara su antigua forma. Bentley estuvo fuera de juego durante meses con una lesión en la rodilla, y después de que expiró su contrato con los Spurs, decidió retirarse a la edad de 29 años. Terminó su carrera en los Spurs con solo dos goles y cinco asistencias en 42 apariciones.

12. Bebe, MF, Manchester United

Firmado en Vitoria Guimaraes (Portugal) por £ 7.9 millones, 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 Quieroz, 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 a transfer which 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’s 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 like they had a manager who had spent the last several seasons getting the most out of a mercurial talent in Suarez.

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. Signed on a free transfer and handed a contract worth £40,000-per-week under the stewardship of Gianluca Vialli, 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 for £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 following week. Brolin refused to return to Leeds the following 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, while 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 Correcto 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 like 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.

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 only made 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 which led to him making his first and only Premier League appearance.

The Dia story feels like it comes from another universe. A man calls Southampton manager Graeme Souness pretending to be World Player of the Year George Weah. The Milan striker recommends Dia, his cousin, suggesting he had just scored two goals for Senegal the prior week and 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.