Ranking the 50 Most Disappointing Soccer Transfers Since 2000
Transfers can be thrilling when they work out, but some deals end up as costly mistakes or baffling missteps. Since the turn of the millennium, big-money moves have surged, and with them, a series of transfers that failed to deliver.
Here we examine 50 transfers that went wrong, based on factors like transfer fee relative to the era, subsequent financial impact, on-pitch performance, and the expectations set by the player's reputation at arrival.
50. Ricardo Quaresma (Porto to Inter Milan, 2008)
- Reported fee: €18.6 million plus player exchange
Once a promising winger alongside Cristiano Ronaldo at Sporting CP, Quaresma’s move to Inter failed spectacularly. Manager Jose Mourinho questioned his attitude and teamwork, and after two years yielding just one goal, he left for Beşiktaş. He also received the Bidone d’Oro award for worst Serie A player in his debut season.
49. Sébastien Haller (Eintracht Frankfurt to West Ham, 2019)
- Reported fee: Up to £45 million with add-ons
Haller’s prolific spells at Frankfurt and Ajax contrast sharply with his underwhelming time at West Ham. Despite initial hopes, he struggled to score consistently and was sold back to Ajax for half the price within 18 months.
48. Jesé Rodríguez (Real Madrid to Paris Saint-Germain, 2016)
- Reported fee: €25 million
Jesé moved from Real Madrid to PSG with high hopes but battled injuries and poor form. Over four seasons, he made only 18 appearances before his contract was terminated following a COVID-19 lockdown breach scandal.
47. Jack Rodwell (Manchester City to Sunderland, 2014)
- Reported fee: £10 million
Rodwell became a symbol of Sunderland's mismanagement, playing fewer than 45 league games over three seasons while earning high wages. Local media labeled him the club’s worst signing when he departed in 2018.
46. Darwin Núñez (Benfica to Liverpool, 2022)
- Reported fee: £64 million rising to £85 million with add-ons
Núñez arrived at Liverpool after a strong scoring season in Portugal but failed to maintain consistency. Known for missed chances and a violent sending-off, he was eventually sold to Al Hilal in Saudi Arabia at age 26.
45. Leonardo Bonucci (Juventus to AC Milan, 2017)
- Reported fee: €42 million
Bonucci’s one-year stint at AC Milan was disappointing despite being named captain. The club finished sixth, and he returned to Juventus in exchange for Mattia Caldara after a season marked by regret.
44. Rasmus Højlund (Atalanta to Manchester United, 2023)
- Reported fee: £64 million rising to £72 million with add-ons
Højlund struggled adapting to the Premier League, enduring a 21-game goalless run before scoring against Leicester. After a weak Europa League final display, he returned to Italy, where Napoli revived his form.
43. Dmytro Chygrynskiy (Shakhtar Donetsk to Barcelona, 2009)
- Reported fee: €25 million
Signed after a strong UEFA Super Cup showing, Chygrynskiy never settled at Barcelona, playing only 14 matches before returning to Shakhtar, leaving behind a curious footnote in Barca’s history.
42. Jackson Martinez (Atlético Madrid to Guangzhou Evergrande, 2016)
- Reported fee: €42 million
After struggling at Atlético Madrid, Martinez’s move to China for a higher fee ended in injury troubles and just 16 appearances before his contract was canceled.
41. Jhon Durán (Aston Villa to Al Nassr, 2024)
- Reported fee: £64.5 million rising to £71 million with add-ons
Despite scoring 12 goals in 18 games for Al Nassr, Durán left less than six months after joining due to personal issues and difficulties adjusting to strict local laws, leading to unsuccessful loan spells in Europe.
40. André Onana (Inter Milan to Manchester United, 2023)
- Reported fee: £43.8 million rising to £47.2 million with add-ons
Onana’s tenure at United was marred by numerous errors and poor distribution. Despite a solid reputation at Ajax and Inter, he was loaned out after a disastrous spell, with ex-player Nemanja Matić calling him one of the worst keepers in club history.
39. Fábio Silva (Porto to Wolverhampton Wanderers, 2020)
- Reported fee: £35 million
Wolves paid a club-record for Silva despite limited top-flight experience. He managed only five goals in 73 appearances and endured multiple loans before being sold to Borussia Dortmund for about half the initial fee.
38. Álvaro Morata (Real Madrid to Chelsea, 2017)
- Reported fee: £60 million
Morata struggled to fill Diego Costa’s shoes at Chelsea, scoring 24 goals in 72 games but lacking the fearlessness and impact Costa had. His tenure deepened the club's infamous 'No. 9 curse.'
37. Renato Sanches (Benfica to Bayern Munich, 2016)
- Reported fee: €35 million rising to €80 million with add-ons
A highly rated youngster from Benfica, Sanches failed to secure a regular role at Bayern, featuring in only one full Bundesliga match without goals or assists before a disappointing loan and eventual sale.
36. Winston Bogarde (Barcelona to Chelsea, 2000)
- Reported fee: Free transfer
Bogarde rarely played at Chelsea but earned a high weekly wage and refused to leave despite being frozen out for nearly three years, famously stating he took the money when offered millions.
35. Ángel Di María (Real Madrid to Manchester United, 2014)
- Reported fee: £59.7 million
Di María arrived at United with a great reputation but faded quickly, scoring only four league goals and departing after a single disappointing season, costing the club over £15 million.
34. Tiémoué Bakayoko (Monaco to Chelsea, 2017)
- Reported fee: £40 million
Bakayoko failed to replicate his Monaco form at Chelsea, playing far more for other clubs during loan spells. His 2018 game against Watford is often cited as the worst Premier League individual performance.
33. Arthur & Miralem Pjanić (Barcelona/Juventus, 2020)
- Arthur’s fee: €72 million rising to €82 million with add-ons
- Pjanić’s fee: €60 million rising to €65 million with add-ons
A costly swap between Barcelona and Juventus involving two midfielders who underperformed for their new clubs, leaving fans and analysts puzzled about the reasoning behind the deal.
32. Juan Sebastián Verón (Lazio to Manchester United, 2001)
- Reported fee: £28.1 million
Verón started well but struggled with the pace of English football and injuries, eventually moving to Chelsea for half the fee and failing to revive his career in England.
31. Eliaquim Mangala (Porto to Manchester City, 2014)
- Reported fee: £31.8 million potentially rising to £42 million
Mangala's City tenure was marked by costly errors including an own goal and a penalty conceded early on, leading to him being replaced and released after loan spells.
30. Kaká (AC Milan to Real Madrid, 2009)
- Reported fee: €68.5 million
Kaká arrived as the world's most expensive player but injuries and loss of form saw him return to Milan on a free, marking one of the biggest transfer losses in football history.
29. Shkodran Mustafi (Valencia to Arsenal, 2016)
- Reported fee: £35 million
Initially promising, Mustafi soon became synonymous with defensive blunders and was part of Arsenal’s poor recruitment during Arsène Wenger’s later years.
28. Mario Balotelli (AC Milan to Liverpool, 2014)
- Reported fee: £16 million
Signed to replace Luis Suárez, Balotelli scored just once in the Premier League and left Liverpool after failing to live up to expectations.
27. Kalvin Phillips (Leeds United to Manchester City, 2022)
- Reported fee: £42 million rising to £45 million with add-ons
Despite shining for England and Leeds, Phillips was criticized for fitness issues at City and struggled with injuries, remaining on a large contract few clubs want to pay.
26. Fernando Torres (Liverpool to Chelsea, 2011)
- Reported fee: £50 million
Torres’s Chelsea period never matched his Liverpool peak. Though he scored 45 goals overall, his Premier League tallies were low and included a famous miss against Manchester United.
25. Jonathan Woodgate (Newcastle United to Real Madrid, 2004)
- Reported fee: £13.4 million
Plagued by injury, Woodgate’s delayed Madrid debut was disastrous with an own goal and sending off. He made only nine league appearances before returning to England.
24. Adrian Mutu (Parma to Chelsea, 2003)
- Reported fee: £15.8 million
Mutu showed potential but was banned for cocaine use, leading to legal battles over contract breaches and debts owed to Chelsea.
23. Paul Pogba (Juventus to Manchester United, 2016)
- Reported fee: £89 million
Pogba’s second stint at United saw flashes of brilliance but was overshadowed by inconsistent effort, unhappiness, and eventual departure for free.
22. Jean-Kévin Augustin (RB Leipzig to Leeds United, 2020)
- Reported fee: Loan with £18.4 million option to buy
Augustin barely played 48 minutes for Leeds but the club was forced to pay a large transfer fee due to contractual obligations, resulting in an expensive failure.
21. Mykhailo Mudryk (Shakhtar Donetsk to Chelsea, 2023)
- Reported fee: £62 million rising to £89 million with add-ons
Mudryk showed promise but was banned for doping violations. After winning an appeal, he faces the challenge of regaining form and reputation.
20. Nicolas Pépé (Lille to Arsenal, 2019)
- Reported fee: £72 million
Pépé’s time at Arsenal was marked by flashy but ineffective dribbling, poor decision-making, and minimal contribution to results.
19. Tanguy Ndombele (Lyon to Tottenham, 2019)
- Reported fee: £63 million
Signed as a successor to Mousa Dembélé, Ndombele struggled with fitness and adapting to the Premier League, leading to multiple loans and eventual contract termination.
18. Danny Drinkwater (Leicester City to Chelsea, 2017)
- Reported fee: £35 million
Drinkwater’s Chelsea career was short and troubled, highlighted by poor performances, red cards, and off-field incidents before retiring in 2022.
17. Andy Carroll (Newcastle United to Liverpool, 2011)
- Reported fee: £35 million
Carroll was a panic signing who failed to fit Liverpool’s style, scoring just six Premier League goals before moving to West Ham for significantly less.
16. Jadon Sancho (Borussia Dortmund to Manchester United, 2021)
- Reported fee: £73 million rising to £78 million with add-ons
Sancho’s move was marred by poor form, public disputes with management, and an inability to regain trust, culminating in a failed loan and a buyout withdrawal by Chelsea.
15. Carlos Tevez (Boca Juniors to Shanghai Shenhua, 2016)
- Reported fee: Disputed but very high
Tevez earned massive wages in China but showed little commitment or fitness, playing just 20 games and describing his stint as a holiday, drawing criticism from fans and himself.
14. Luka Jović (Eintracht Frankfurt to Real Madrid, 2019)
- Reported fee: €60 million
Jović’s rapid rise stalled at Madrid due to injuries and off-field issues, limiting him to three goals before moving on a free transfer.
13. Gaizka Mendieta (Valencia to Lazio, 2001)
- Reported fee: €48 million
A former European best midfielder, Mendieta failed to score in 31 appearances for Lazio, leading to a quick move to Barcelona.
12. Zlatan Ibrahimović (Inter Milan to Barcelona, 2010)
- Reported fee: €46.2 million plus Samuel Eto’o
Zlatan scored 21 goals but clashed with Pep Guardiola and struggled with Messi’s shadow, leading to a swift return to Italy.
11. Andriy Shevchenko (AC Milan to Chelsea, 2006)
- Reported fee: £30 million
Shevchenko’s prolific Milan form did not translate in England, managing just nine league goals before returning to Milan and then Ukraine.
10. João Félix (Benfica to Atlético Madrid, 2019)
- Reported fee: €126 million
Félix’s style didn’t suit Atlético’s intensity; while part of a title-winning squad, his inconsistency and lack of adaptation led to criticism and a later move away.
9. Kepa Arrizabalaga (Athletic Club to Chelsea, 2018)
- Reported fee: £72 million
Record-breaking goalkeeper signing Kepa failed to justify his fee with shaky performances, including a refusal to be substituted and a penalty shootout miss, eventually leaving Chelsea for £5 million.
8. Alexis Sánchez (Arsenal to Manchester United, 2018)
- Reported fee: Player swap with Henrikh Mkhitaryan
Sánchez’s enormous wages and poor form burdened United, scoring only three league goals before moving to Inter Milan after two dismal seasons.
7. Ousmane Dembélé (Borussia Dortmund to Barcelona, 2017)
- Reported fee: €105 million rising to €145 million with add-ons
Dembélé suffered from injuries and disciplinary problems, missing 85 games and failing to meet the expectations tied to his hefty price tag before eventually thriving elsewhere.
6. Antony (Ajax to Manchester United, 2022)
- Reported fee: £81.3 million rising to £86.3 million with add-ons
Initially promising with early goals, Antony’s time at United descended into a series of erratic performances and antics, ending with a sale to Real Betis for a fraction of the price.
5. Romelu Lukaku (Inter Milan to Chelsea, 2021)
- Reported fee: £97.5 million
Lukaku’s return to Chelsea was plagued by dissatisfaction and lack of fit, leading to a quick loan back to Inter at a steep loss for the Blues.
4. Philippe Coutinho (Liverpool to Barcelona, 2018)
- Reported fee: £105 million rising to £142 million with add-ons
Coutinho failed to find his role at Barcelona and was loaned out after playing a part in their historic Champions League collapse, before a modest transfer back to the Premier League.
3. Antoine Griezmann (Atlético Madrid to Barcelona, 2021)
- Reported fee: €120 million
Griezmann’s expensive move was disappointing on the pitch, and his massive contract contributed to Barcelona’s inability to renew Messi, indirectly causing a major club crisis.
2. Neymar (Paris Saint-Germain to Al Hilal, 2023)
- Reported fee: €90 million
Neymar's big-money move to Saudi Arabia backfired due to injuries and decline, managing just seven appearances before a mutual contract termination.
1. Eden Hazard (Chelsea to Real Madrid, 2019)
- Reported fee: €100 million rising to €146 million with add-ons
Expected to replace Cristiano Ronaldo, Hazard’s Real Madrid stint was plagued by weight issues, injuries, and poor form, scoring just seven goals before eventually retiring.
