Bill ConnellyFeb 11, 2026, 09:59 AM ETCloseBill Connelly is a writer for ESPN. He covers college football, soccer and tennis. He has been at ESPN since 2019.Follow on XMultiple Authors
11. Alexis Sánchez, FW, Manchester United Signed from Arsenal for €34 million (and a swap for Henrikh Mkhitaryan), 2018-19
50. Davy Klaassen, CM, Everton Signed from Ajax for €27 million, 2017-18
49. Casemiro, DM, Manchester United Signed from Real Madrid for €70.7 million, 2022-23
48. Gastón Ramírez, AM, Southampton Signed from Bologna for €15.2 million, 2012-13
47. Roberto Soldado, CF, Tottenham Hotspur Signed from Valencia for €30 million, 2013-14
46. Alberto Aquilani, MF, Liverpool Signed from Roma for €20 million, 2009-10
45. Owen Hargreaves, DM, Manchester United Signed from Bayern Munich for €25 million, 2007-08
44. Marco Boogers, CF, West Ham United Signed from Sparta Rotterdam for €440,000, 1994-95
43. Timo Werner, FW, Chelsea Signed from RB Leipzig for €53 million, 2020-21
42. Seth Johnson, MF, Leeds United Signed from Derby County for €11.5 million, 2001-02
41. Michael Owen, FW, Newcastle United Signed from Real Madrid for €25 million, 2005-06
40. Fernando Torres, FW, Chelsea Signed from Liverpool for €58.5 million, 2010-11
39. Sergey Rebrov, FW, Tottenham Signed from Dynamo Kyiv (Ukraine) for €18 million, 2000-01
38. Per Kroldrup, DF, Everton Signed from Udinese for €6.8 million, 2005-06
37. Cristiano Ronaldo, CF, Manchester United Signed from Juventus for €17 million, 2021-22
36. Ángel Di María, FW, Manchester United Signed from Real Madrid for €75 million, 2014-15
35. Jack Rodwell, DM, Sunderland Signed from Manchester City for €12.5 million, 2014-15
34. Agustin Delgado, FW, Southampton Signed from Necaxa for €5.8 million, 2001-02
33. Roger Johnson, CB, Wolves Signed from Birmingham City for €8 million, 2011-12
32. Alexander Isak, CF, Liverpool Signed from Newcastle for €145 million, 2025-26
31. Jack Grealish, LW, Manchester City Signed from Aston Villa for €117.5 million, 2021-22
30. Juan Sebastian Veron, MF, Manchester United Signed from Lazio for €42.6 million, 2001-02
29. Giannelli Imbula, DM, Stoke City Signed from Porto for €24.3 million, 2015-16
28. Saido Berahino, FW, Stoke City Signed from West Bromwich Albion for €13.9 million, 2016-17
27. Adrian Mutu, FW, Chelsea Signed from Parma for €22.7 million, 2003-04
26. Kevin Davies, CF, Blackburn Rovers Signed from Southampton for €11.3 million, 1998-99
25. Kepa Arrizabalaga, GK, Chelsea Signed from Athletic Club for €80 million, 2018-19
24. Tanguy Ndombele, MF, Tottenham Hotspur Signed from Lyon for €62 million, 2019-20
23. Eliaquim Mangala, CB, Manchester City Signed from Porto for €45 million, 2014-15
22. Rasmus Hojlund, CF, Manchester United Signed from Atalanta for €77.8 million, 2023-24
21. Mario Balotelli, FW, Liverpool Signed from AC Milan for €20 million, 2014-15
20. Andy Carroll, FW, Liverpool Signed from Newcastle United for €41 million, 2010-11
19. Bebe, MF, Manchester United Signed from Vitoria Guimaraes for €8.8 million, 2010-11
18. David Bentley, RW, Tottenham Hotspur Signed from Blackburn for €22 million, 2008-09
17. Andriy Shevchenko, FW, Chelsea Signed from AC Milan for €43.9 million, 2006-07
16. Winston Bogarde, CB, Chelsea Signed from Barcelona on a free transfer, 2000-01
15. Dani Osvaldo, FW, Southampton Signed from Roma for €15.1 million, 2013-14
14. Steve Marlet, FW, Fulham Signed from Lyon for €17.6 million, 2001-02
13. Wesley Fofana, DF, Chelsea Signed from Leicester City for €80.4 million, 2022-23
12. Bosko Balaban, CF, Aston Villa Signed from Dinamo Zagreb for €7.8 million, 2001-02
10. Kalvin Phillips, DM, Manchester City Signed from Leeds United for €49 million, 2022-23
9. Tomas Brolin, MF, Leeds United Signed from Parma for €5.3 million, 1995-96
8. Jadon Sancho, RW, Manchester United Signed from Borussia Dortmund for €85 million, 2021-22
7. Romelu Lukaku, CF, Chelsea Signed from Inter Milan for €113 million, 2021-22
6. Ricky Alvarez, MF, Sunderland Signed from Inter Milan for €10.5 million, 2015-16
5. Danny Drinkwater, CM, Chelsea Signed from Leicester City for €37.9 million, 2017-18
4. Ali Dia, FW, Southampton Signed on a free transfer, 1996-97
3. Nicolas Pépé, RW, Arsenal Signed from Lille for €80 million, 2019-20
2. Antony, RW, Manchester United Signed from Ajax for €95 million, 2022-23
1. Mykhaylo Mudryk, LW, Chelsea Signed from Shakhtar Donetsk for €70 million, 2022-23
When you hit on a run of transfers, it can change everything. Most of the great runs of the Premier League era were built around exactly that, and, predictably, some of the best teams in league history have been built with some of the best transfers.
The opposite, however, is also true. The richest clubs in the Premier League have sometimes been able to overcome some poor decisions in the transfer market. Chelsea still won the Champions League in 2021 despite a number of failures, and Manchester City still won lots of recent league titles despite failing to get their money’s worth for guys like Kalvin Phillips. Still, it usually catches up to you eventually.
Maybe you ignored a player’s injury history, and it backfired. Maybe a guy’s injury history began after he made a big-money move to your club. Maybe you immediately fire the manager who wanted him, and he never settles. (And maybe his contract is big enough that he’s happy to sit the bench despite your best efforts to move him.) Maybe he gets into fights with teammates. Maybe you signed a guy right after his peak. Maybe you simply negotiated with yourself and dramatically overpaid.
– Connelly: The best 50 transfers in Premier League history – O’Hanlon: Ranking club, national team coaching jobs from best to worst – Lindop: Where did it go wrong for Arne Slot and Liverpool?
Whatever the reason, some awful transfers stand out from the pack. You’ll find some themes as we go along, but here are the 50 worst transfers in Premier League history.
A particularly unhappy piece of business. Klaassen arrived as a celebrated 24-year-old midfielder — he had spent his previous two seasons at Ajax as captain — and was regarded as a key piece for manager and fellow Dutchman Ronald Koeman. One year and just 251 Premier League minutes later, he left for Werder Bremen at half the price. He couldn’t prevent Koeman from being fired, and he didn’t impress either Sam Allardyce or, the following summer, Marco Silva, either.
There’s honestly enough material that you could just make a pretty lengthy and readable “Worst Premier League transfers of 2022-23” list. Five players made this list from those two windows, plus four more from 2021-22, and to be fair to Casemiro, he seemed absolutely worth the money for a moment. (He wasn’t even close to the worst signing United made that season.)
It’s hard to judge a transfer harshly when injuries play such a major role in a player’s failure, but with Hargreaves, there was plenty of warning: He had topped 1,700 league minutes just once in his previous five seasons with Bayern. He was excellent in his first season at Old Trafford, playing all 120 minutes in United’s Champions League final win over Chelsea. But recurring knee issues took over from there, and he made only five more appearances with the club after 2007-08.
Here’s one for the “absolute no-brainer that somehow didn’t work out” department. After moving from Stuttgart at age 20, Werner was otherworldly for RB Leipzig, scoring 95 goals in four seasons in all competitions. He was ridiculously fast in both pressing and counterattacking, and though his finishing was never elite, it was average at worst.
He signed with Chelsea over a major pursuit from Liverpool and others, but in two seasons at Stamford Bridge his finishing abandoned him: In all competitions, he scored 23 goals from shots worth 34.0 xG. He started in Chelsea’s Champions League final win over Manchester City in 2021, and hey, 23 goals in two seasons isn’t terrible. But it also didn’t clear the bar either his résumé or his price tag commanded.
You know what, though? That alone might have been worth the price. Roman Abramovich’s Blues landed a long-awaited Champions League title when Torres scored to beat Barca in the semifinals and Chelsea upset Bayern on penalties in the final. But as the most expensive Premier League transfer to date, Torres basically showed up only in continental play. In 3½ seasons, he scored nearly as many goals in UEFA competitions (17) as Premier League matches (20).
By 2021, Cristiano Ronaldo was done making huge clubs better. A desperate Juventus had taken him from Real Madrid for a €117 million fee, but their point total regressed every season he was there, and the Champions League boost he was supposed to provide never arrived. And while the transfer fee required to send him back to Manchester United wasn’t particularly onerous, his salary requirements remained immense.
Ronaldo scored 18 league goals in his only full season back in Manchester, but United sank from second to sixth in the league, and then-manager Erik ten Hag had no interest in reconfiguring his system to account for Ronaldo’s increasingly limited skill set. (He could score, but he didn’t press, and he needed the entire attack built around him.) United sold a lot of shirts in bringing him back, but accomplished little else, and his contract was terminated 15 months after his arrival.
A year after his arrival, Delgado declared he was leaving the club because “it’s obvious the coach [Gordon Strachan] hates me and South Americans in general.” Then he surprised the club even more by returning soon after, not that it did him much good. He scored twice in just 15 appearances, then returned to the Ecuadorian Serie A in 2004.
When you sign for such an outlandish transfer fee, you basically start on this list and have to play yourself off of it. Isak might do so eventually, but in his first six months with Liverpool, the 26-year-old has scored just three goals in 777 minutes in all competitions, and he has missed the last two months with injury. It’s been a disastrous start for a player who scored 62 goals in three seasons with Newcastle.