The transfer window is a time of hope and excitement. A time to make transformative additions that can revive a struggling team or put trophy-chasing sides over the top. It’s also a time where expensive, crippling mistakes are made. For every brilliant deal and shrewd piece of business, there are dozens of signings that, for one reason or another, go bust. Some of them in spectacular fashion.
This week, while the wheeling and dealing is in full swing, we’re ranking the 30 worst signings in soccer history. Compiled by theScore’s soccer editors, our list features prototypical high-priced flops along with some of the more mystifying moves that ruined careers, damaged reputations, and set clubs back several years. The three-part series continues below.
Follow the entire series this week:
| Jan. 20 | Jan. 22 | Jan. 24 |
|---|---|---|
| 30-21 | 20-11 | 10-1 |
20. Zlatan Ibrahimovic (Barcelona)
Signed from Inter Milan for initial €46 million, plus Samuel Eto’o in 2009
Things got ugly after Ibrahimovic left Inter. He said the Italian club wouldn’t win anything without him, only to have his proclamation backfire in spectacular fashion after he joined Barcelona for a huge package. But his ill-fated spell with Barcelona was even more acrimonious. A strained relationship with Pep Guardiola was a major factor why Ibrahimovic’s stay lasted only a season. The situation came to a boil when Barca were knocked out of the Champions League in 2010 by none other than Inter. Ibrahimovic, substituted following a dreadful outing, claims he unleashed a furious tirade after the team’s semifinal exit, calling Guardiola a “spineless coward.” Eto’o, meanwhile, was vital in helping Inter win the treble in 2009-10. – Gordon Brunt
19. Lorenzo Insigne (Toronto FC)
Free transfer from Napoli in 2022
Toronto FC have made many terrible marquee signings over the years, but Insigne tops the lot. Federico Bernardeschi, another Italian who arrived in 2022, has shown occasional glimpses of talent. Insigne is a different story altogether: 14 goals, 11 assists, and general indifference over 54 appearances; a guaranteed annual income of $15.4 million that’s trumped by only Lionel Messi in MLS; constant injury problems; and a reputation for causing off-field drama. TFC are reportedly trying to offload him before the 2025 season kicks off, but the financial burden and unrest that Insigne caused will be felt for some time yet. – Daniel Rouse
18. Luka Jovic (Real Madrid)
Signed from Eintracht Frankfurt for initial €65 million in 2019
Jovic was coming off the best season of his young career when Real Madrid came calling with the offer of a lifetime. Jovic was 21 at the time and saw an opportunity to star in a team that had struggled to move on from Cristiano Ronaldo and coach Zinedine Zidane. But injuries and the COVID-19 pandemic made it impossible for Jovic to make his mark. Karim Benzema took charge of Madrid’s attack, leaving Jovic on the sidelines. Madrid eventually cut their losses, sending the Serbian to Fiorentina on a free transfer in 2022 and even agreeing to cover his wages. Jovic finished his Real Madrid career with three league goals. – Anthony Lopopolo
17. Mykhailo Mudryk (Chelsea)
Signed from Shakhtar Donetsk for initial €70 million in 2023
This one’s still percolating, but Mudryk’s transfer has all the hallmarks of being another expensive dud for Chelsea. Arriving as the possible solution to Chelsea’s attacking problems, Mudryk has instead turned into the poster boy for the dysfunctional era under co-owner Todd Boehly. There was enough hype about Mudryk to spark a reported bidding war between the Blues and Arsenal after a breakthrough season at Shakhtar Donetsk. But Mudryk has only ever shown brief glimpses of the star many predicted him to be. Chelsea will hope he can figure it out before his contract expires in six years. With a possible doping suspension looming and the transfer fee potentially reaching €100 million, this move could easily end up being much higher if we revisit this list in a few years. – Brunt
16. Jack Rodwell (Sunderland)
Signed from Manchester City for £10 million in 2014
Listing the worst Sunderland transfers from the past two decades would be difficult. There are so many. But the overall outlay on Rodwell was baffling. Sunderland signed the midfielder after two injury-hit and underwhelming seasons with Manchester City. His weekly pay packet of £70,000 was extremely generous, and the contract became an even bigger burden on the struggling club because it didn’t include a clause to reduce his wages after relegation. Sunderland then suffered a second consecutive relegation as Rodwell logged only 105 Championship minutes. Rodwell defined an era where many Sunderland players just didn’t seem to care. – Rouse
15. Gaizka Mendieta (Lazio)
Signed from Valencia for €48 million in 2001
Mendieta helped Valencia reach back-to-back Champions League finals before joining Lazio in 2001 as the sixth-most expensive player of all time. Mendieta arrived as a kind of savior as Lazio had failed to defend their Serie A title and sold off Pavel Nedved and Juan Sebastian Veron. In reality, the move signaled the beginning of the end of the influential Spanish midfielder’s career. Mendieta made just 20 Serie A appearances for Lazio, and subsequent attempts to revive his career at Barcelona and Middlesbrough yielded negative results. – Lopopolo
14. Danny Drinkwater (Chelsea)
Signed from Leicester City for £35 million in 2017
A year after signing N’Golo Kante, Chelsea went back to the Leicester City well, frantically adding Drinkwater on deadline day hoping for the same results. However, the pity for Leicester didn’t last long after losing another one of the stars from their 2016 Premier League-winning team. Chelsea changed coaches after Drinkwater’s frustrating debut season in a move that all but ended his Blues career. After failing to establish himself as a first-team player, Drinkwater’s downward spiral gained momentum with controversial loan spells at Burnley and Aston Villa, which included a run-in with police and reportedly headbutting a teammate. He retired at 33 after his five-year Chelsea contract ended, ultimately making just five Premier League starts for the west London club. – Brunt
13. Antony (Manchester United)
Signed from Ajax for €95 million in 2022
Few could understand why United paid top dollar for Antony. He ranked outside the top 10 in dribbles completed in the Eredivisie and outside the top 20 in goals scored. But Erik ten Hag coached him at Ajax and clearly convinced United he was worth the money. What a gross miscalculation. Antony famously went 31 games without scoring for the Red Devils and failed to make a single Premier League start this season. Now the coach who vouched for him is long gone, and the Brazilian himself is seemingly on his way to Real Betis on a loan deal that doubles as a wicked indictment of United’s frivolous transfer policy. – Lopopolo
12. Andriy Shevchenko (Chelsea)
Signed from AC Milan for £31 million in 2006
Shevchenko was one of the world’s most feared marksmen over seven years at AC Milan, scoring 173 goals and winning the 2004 Ballon d’Or award. He joined Chelsea seemingly at his peak. Jose Mourinho said the striker was his “first choice” since he took over at Stamford Bridge. But Shevchenko looked much older than 29 when he arrived in England and was injury prone. He tallied nine goals in 48 Premier League outings and even endured a miserable loan spell back at Milan, where he failed to register a goal in 18 Serie A appearances. He was broken. – Rouse
11. Carlos Tevez (Shanghai Shenhua)
Signed from Boca Juniors for €84 million in 2016
There’s no better example of how ridiculous Chinese Super League spending became than Tevez’s transfer to Shanghai Shenhua. The club made him the richest player in the world with a contract reportedly worth £615,000 a week. But that wasn’t enough to motivate the Argentine, who was 32 at the time and struggled with poor form, weight issues, and home sickness. Tevez eventually engineered a return to Boca Juniors and admitted he was “on holiday for seven months” in China. His departure was followed by sweeping reforms that brought an end to the wild spending among Chinese Super League teams. – Brunt
The series concludes Friday with the top 10.
