Ranking the 25 Biggest Transfer Flops in Premier League History
While the Premier League has seen some of the best talents in football history, it's also been home to shocking misjudgments in the transfer market. Here are the top 25 transfer flops ever seen in England’s top flight — counting down from 25 to the ultimate disaster.
25. Savio Nsereko – West Ham
West Ham smashed their transfer record to sign Savio in 2009, hoping he would replace Craig Bellamy. The young German barely featured, made just 11 appearances, and was sold within six months at a significant loss.
24. Afonso Alves – Middlesbrough
Middlesbrough spent £12.5 million on Alves after his goal-filled time in the Eredivisie. But he failed to adapt to English football and only scored four league goals in his final season as Boro were relegated.
23. Massimo Taibi – Manchester United
Brought in to replace Peter Schmeichel, Taibi lasted just four games at United. A series of calamitous errors saw him dubbed “The Blind Venetian” and sent back to Italy within months.
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22. Jo – Manchester City
Signed for a then club-record £18 million in 2008, Jo managed just one league goal. Overshadowed by City’s other signings, he became a symbol of pre-Mansour transfer waste.
21. Eric Djemba-Djemba – Manchester United
Meant to be Roy Keane's successor, Djemba-Djemba never lived up to the hype. He only lasted 18 months at United before being shipped off to Aston Villa.
20. Tomas Brolin – Leeds United
Once a star at Parma, Brolin arrived at Leeds overweight and out of shape. His performances were so underwhelming he soon left football altogether to sell vacuum cleaners.
19. Jack Rodwell – Sunderland
Rodwell joined Sunderland after flopping at Manchester City, but things got worse. He was plagued by injuries and criticism after refusing to lower his wages despite Sunderland’s financial crisis and relegation.
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18. Darwin Nunez – Liverpool
Signed from Benfica for up to £85 million, Nunez had flashes of brilliance but lacked consistency. After 25 goals in 95 Premier League appearances, he was sold to Al-Hilal in 2025.
17. Timo Werner – Chelsea
Brought in to solve Chelsea’s striker issues, Werner struggled with finishing and confidence. Despite his pace, he only managed six league goals in his debut season and returned to RB Leipzig after two disappointing years.
16. Kleberson – Manchester United
Ferguson signed Kleberson expecting the midfielder who shone at the 2002 World Cup. Instead, United got a nervous player completely out of depth, and he was sold after just 30 appearances.
15. Andriy Shevchenko – Chelsea
Despite dominating Serie A, Shevchenko never adjusted to the Premier League. His return of 22 goals in 77 games was a poor return on Chelsea’s £30 million investment.
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14. Fernando Torres – Chelsea
Chelsea paid £50 million for Torres, but he never recaptured his Liverpool form. He struggled with injuries and confidence, and his iconic first goal came after a nine-game drought.
13. Adrian Mutu – Chelsea
Mutu's Chelsea career ended in scandal after a positive cocaine test led to his dismissal. He was later ordered to pay millions in damages, making him one of football’s costliest off-field disasters.
12. Nicolas Pepe – Arsenal
Pepe arrived for a club-record £72 million but never truly fit into Arsenal’s system. Inconsistent form and Bukayo Saka’s emergence made him surplus to requirements before he eventually left for free.
11. Andy Carroll – Liverpool
Signed for £36 million on the same day as Luis Suárez, Carroll failed to live up to the price tag. Injuries and poor form limited him to 11 goals, while Suárez’s success only highlighted Carroll’s flop.
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10. Mykhailo Mudryk – Chelsea
Hijacked from Arsenal in a last-minute deal worth £88.5 million, Mudryk never looked settled. Suspended in 2025 for doping, his Chelsea future now hangs in doubt after minimal impact.
9. Antony – Manchester United
United paid £86 million for Antony, but he has yet to justify even a fraction of that fee. His inconsistency and lack of end product have made him one of United’s most frustrating attackers.
8. Jadon Sancho – Manchester United
After years of pursuit, United finally signed Sancho for £73 million, only for him to clash with Erik ten Hag and fall out of favor. A loan return to Dortmund followed after minimal league contributions.
7. Kepa Arrizabalaga – Chelsea
The most expensive goalkeeper in the world never played like one. Kepa’s performances were shaky from the start, leading to several benchings and repeated attempts by Chelsea to replace him.
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6. Angel Di Maria – Manchester United
Di Maria looked electric in his first month but quickly lost interest. After just one season, he forced a move to PSG, having failed to adapt to English football or life off the pitch.
5. Donny van de Beek – Manchester United
Highly rated from his Ajax days, Van de Beek never found a role at United. Ignored by multiple managers, he eventually left with only 62 appearances in four years.
4. Danny Drinkwater – Chelsea
Chelsea spent £35 million to reunite Drinkwater with Kanté, but he barely played. From poor form to training ground fights, his time at Stamford Bridge was a complete bust.
3. Bebe – Manchester United
Signed without ever being scouted by Ferguson, Bebe was miles off Premier League quality. One of the strangest and most baffling signings United ever made.
2. Romelu Lukaku – Chelsea
Chelsea re-signed Lukaku for nearly £100 million expecting a world-class striker. After just one season and a controversial interview, he was loaned back to Inter, leaving fans furious.
1. Ali Dia – Southampton
The greatest Premier League con artist of all time. Ali Dia convinced Southampton he was George Weah’s cousin, played one game, and proved beyond doubt he had no business on a football pitch.
