Bill Connelly
Multiple Authors
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.
There are lots of ways for a transfer to go south.
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.
50. Davy Klaassen, CM, Everton
Signed from Ajax for €27 million, 2017-18
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.)
The Brazil star provided solid veteran leadership, plus seven goals and six assists, for a United team that jumped from sixth to third in the Premier League, won the League Cup and reached the FA Cup final. That was three years ago, however, and the problem with signing a 30-year-old for mega money is he’s only going to get older. While commanding a yearly salary somewhere in the €20 million range, Casemiro’s production diminished significantly over the next two seasons as United fell to eighth, then 15th.
He has perked up a bit of late, but he had no chance of living up to his salary.
48. Gastón Ramírez, AM, Southampton
Signed from Bologna for €15.2 million, 2012-13
After two straight promotions got them back to the Premier League, Southampton would enjoy a nice run of first-division success in the 2010s, but Ramirez was responsible for very little of it. After generating eight goals and four assists in league play for Bologna in 2011-12, he was the star of a huge class of young attackers that Southampton would bring in. But over parts of four Premier League seasons with the Saints, he produced just six goals and seven assists. After multiple loans, he would leave for second-division Middlesbrough on a free transfer before eventually enjoying a few solid seasons with Sampdoria. Some people can only find themselves in Italy.
47. Roberto Soldado, CF, Tottenham Hotspur
Signed from Valencia for €30 million, 2013-14
Like Klaassen, Soldado left at a 50 percent discount not long after his arrival. A record signing for Spurs after a 30-goal campaign at Valencia, he scored three goals in his first week of action at the club — one against Crystal Palace in the Premier League, two against Dinamo Tbilisi in the Europa League — but it was all downhill from there. He would score five more goals over 14 Europa League matches, but he managed just 29 Premier League starts and seven goals over two seasons. He left for Villarreal for €16 million in 2015.
46. Alberto Aquilani, MF, Liverpool
Signed from Roma for €20 million, 2009-10
After five excellent seasons with Roma, Aquilani left because of Roma’s financial struggles, and though he was envisioned as a replacement for Xabi Alonso, he just slightly failed to clear that bar. He started only nine league matches for Rafa Benitez’s Liverpool, and though he did produce six league assists, the move was quickly acknowledged as a mistake by all parties. He was loaned to Juventus for one season and to AC Milan for another before leaving for Fiorentina for just a €2 million transfer in 2012.
45. Owen Hargreaves, DM, Manchester United
Signed from Bayern Munich for €25 million, 2007-08
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.
There aren’t many signings from the 1990s on the list as, proportionally speaking, there wasn’t quite as much money getting wasted. But you have to save a place on the list for Boogers, who, in his second appearance, made one of the nastiest tackles in league history on Gary Neville, went down with a knee injury soon after returning from suspension and was shipped back to the Netherlands by February of 1998, never to be heard from (in England) again.
43. Timo Werner, FW, Chelsea
Signed from RB Leipzig for €53 million, 2020-21
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.
42. Seth Johnson, MF, Leeds United
Signed from Derby County for €11.5 million, 2001-02
Signed on the heels of Leeds’ Champions League semifinal run, Johnson benefited from the club’s desperation to remain relevant and Champions League-worthy and took on a hefty pay raise. Leeds were stuck with that contract when, after collapsing financially and falling into administration, they were relegated a few years later. Johnson wasn’t terrible, but he battled endless injuries and made just 15 Premier League starts in his first two seasons. And as the story goes, he returned to Derby after his Leeds release, where he was very impressed by the facilities that his sale had allowed the club to build.
41. Michael Owen, FW, Newcastle United
Signed from Real Madrid for €25 million, 2005-06
Still only 25 after a long, successful stint at Liverpool — and a much shorter, less successful stint at Real Madrid — Owen arrived at St. James’ Park as Newcastle’s record signing and designated replacement for the retiring Alan Shearer. (There are lots of record signings on this list.) He was slowed by an injury at first but still scored seven goals in his first eight Premier League matches with the club. But he broke his foot on New Year’s Eve and missed most of four months, then he had an ACL tear at the 2006 World Cup and missed most of 2006-07. He rebounded for a pair of decent seasons, but “30 goals and 79 total appearances in four years” was not quite the return Newcastle were anticipating.
40. Fernando Torres, FW, Chelsea
Signed from Liverpool for €58.5 million, 2010-11
Chelsea basically paid €58.5 million for this:
Fernando Torres vs Barcelona 🔵
Iconic.#UCL pic.twitter.com/Ma2z6kCTXt
— UEFA Champions League (@ChampionsLeague) November 25, 2025
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).
39. Sergey Rebrov, FW, Tottenham
Signed from Dynamo Kyiv (Ukraine) for €18 million, 2000-01
Including qualification matches, Rebrov scored 31 goals with 12 assists in the Champions League during a career that spanned nearly two decades. Unfortunately, none of those came with Tottenham. Signed after a brilliant, 30-goal campaign with Dynamo Kyiv (his second in three years), where he had formed a memorable partnership with Andrey Shevchenko, Rebrov scored just 15 goals in all competitions over two seasons in North London and was loaned out for a pair of unproductive seasons with Fenerbahce. He left as a free transfer four years after his arrival.
38. Per Kroldrup, DF, Everton
Signed from Udinese for €6.8 million, 2005-06
Blink and you might have missed Kroldrup’s Everton stint. The 6-foot-4 Dane arrived after playing a big role in Udinese’s stirring rise, but he immediately suffered a groin injury and didn’t make his debut until late-December … and then left for Fiorentina for €4 million about three weeks later. It’s good to admit your mistake and move on, I guess, but Everton basically lit a few million Euros on fire.
37. Cristiano Ronaldo, CF, Manchester United
Signed from Juventus for €17 million, 2021-22
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.
36. Ángel Di María, FW, Manchester United
Signed from Real Madrid for €75 million, 2014-15
In the four years before his arrival in Manchester, di Maria averaged 5.5 goals and 12.5 assists in league play with Real Madrid. In the five years after he left United, he averaged 9.4 and 11.2, respectively, with PSG. But the most expensive Premier League transfer to date lasted just one miserable season at Old Trafford. It started well enough — he won the Premier League’s player of the month in September 2014 — but after he suffered a hamstring injury in November, nothing was ever the same. He was scapegoated for United’s disappointing season under Louis van Gaal, his house was robbed and, well, his wife hated the food.
This move failed in just about every way a move can fail, although it was redeemed a bit by the solid transfer fee (€63 million) PSG sent United’s way.
35. Jack Rodwell, DM, Sunderland
Signed from Manchester City for €12.5 million, 2014-15
Rodwell was solid at Everton as a teenager but made next to no impact in two seasons with Manchester City; that didn’t stop Sunderland from hungrily laying down significant money — with no “your salary will go down if we get relegated” clause — to bring him to the Stadium of Light in 2014. He was constantly injured and did nothing to prevent the Black Cats from going down in 2017, and he was one of the most expensive players in the second division while playing just twice in 2017-18 as Sunderland got relegated again.
34. Agustin Delgado, FW, Southampton
Signed from Necaxa for €5.8 million, 2001-02
A star for Ecuador — he scored 31 times in 71 national team appearances, including 13 in 21 matches in 2000-01 — Delgado evidently just couldn’t stand being so far away from home. He played just two matches for Southampton in his first season due to injuries, then angered the club after suddenly being healthy enough to play all three of Ecuador’s World Cup matches (and score against Mexico).
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.
(He would score twice more at the 2006 World Cup.)
33. Roger Johnson, CB, Wolves
Signed from Birmingham City for €8 million, 2011-12
He’s in no way the most expensive transfer on the list, but in terms of return on investment, it’s hard to get less out of a transfer. Wolves manager Mick McCarthy almost immediately made the 6-foot-3 defender the captain upon his arrival, but McCarthy was sacked in February on the way to relegation, and Johnson allegedly turned up drunk for training in March. He captained a second straight relegation the next season, too. He quickly left via free transfer, and while Wolves rebounded and rose back up the English pyramid, Johnson only fell further.
32. Alexander Isak, CF, Liverpool
Signed from Newcastle for €145 million, 2025-26
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.
31. Jack Grealish, LW, Manchester City
Signed from Aston Villa for €117.5 million, 2021-22
Over four seasons, €117.5 million (and around €18 million a year in salary) bought Manchester City 17 goals and 23 assists. This outlay didn’t stop big-spending City from winning three Premier League titles and a long-awaited Champions League crown in 2022-23 — and certainly didn’t stop Grealish from celebrating said Champions League win — but when you’re best remembered for your performance on a parade route, it’s safe to say you didn’t live up to your billing.
30. Juan Sebastian Veron, MF, Manchester United
Signed from Lazio for €42.6 million, 2001-02
Understanding the need to adapt tactically to keep up in Europe, Sir Alex Ferguson’s United made the 26-year-old Veron the most expensive transfer in English history to date. Two years later, he left for Chelsea at half the price. He scored three goals in September 2001 and won the Premier League’s player of the month award, but he would score just five more league goals for the club; Ferguson couldn’t solve how to incorporate his skill set into a talented but perhaps set-in-its-ways midfield, and Veron found it harder than he expected to adapt to ball in England.
In fact, you could make a case that his move to Chelsea should have been on this list as well: He was far more of a known quantity, and the Blues still spent over €20 million on him.
29. Giannelli Imbula, DM, Stoke City
Signed from Porto for €24.3 million, 2015-16
After two straight top-half-of-the-table finishes, Stoke seemingly attempted to shift from thinking like a scrappy overachiever to making moves like a genuine top club in England. Things fell apart quickly. As yet another club-record signing on this list — someone Marcelo Bielsa once said had the tools to become one of the best midfielders in the world — Imbula managed only 28 appearances for the club. He showed promise late in 2015-16, but within a year he was done. He was loaned out amid complaints about his attitude as Stoke battled relegation, and his contract was bought out early.
28. Saido Berahino, FW, Stoke City
Signed from West Bromwich Albion for €13.9 million, 2016-17
When he left for Stoke (for what was a pretty hefty chunk of change for the club), West Brom manager Tony Pulis said Berahino “needs to get his act together.” That’s what we in the business call a red flag. He had enjoyed a 14-goal campaign for West Brom in 2014-15, but that’s 14 more goals than he scored in 28 league appearances for Stoke, who were relegated in 2017-18. He scored only three goals in the Championship the next season and never played for the club again after a drunk driving arrest.
27. Adrian Mutu, FW, Chelsea
Signed from Parma for €22.7 million, 2003-04
Mutu was a major piece of new Chelsea owner Roman Abramovich’s initial spending spree. He had enjoyed a brilliant Serie A campaign in 2002-03, scoring 17 goals with 12 assists as Parma finished fifth in the league. He scored four goals in his first three Chelsea appearances, but it was all downhill from there. He scored just six more goals all season, then battled with new manager Jose Mourinho, tested positive for cocaine and left the club after just 14 months. He didn’t hold the Blues back all that much, but he certainly wasn’t a solid investment either.
26. Kevin Davies, CF, Blackburn Rovers
Signed from Southampton for €11.3 million, 1998-99
With Blackburn having jumped back up to sixth place (and qualified for the UEFA Cup) in 1997-98, they spent big to replenish and expand their squad. Davies had just scored 12 goals in all competitions for Southampton at age 20, and he was the most expensive of the new pieces. He scored two only goals in 27 appearances. The Rovers lost in the first round of the UEFA Cup and pulled just nine points from their first 15 Premier League matches. They were relegated, and Davies was headed back to Southampton barely a year after his arrival.
There have been a little over 50 players acquired for a transfer fee of €75 million or more. Only one was a goalkeeper. In bringing Kepa from Bilbao, Chelsea broke the transfer record Liverpool had only recently set for Alisson. He performed pretty well at first, though his debut season was remembered primarily for his refusal to be subbed out before a penalty shootout (that he lost). But he struggled in year two, and he made only 11 combined league appearances in years three and four.
After spending two seasons on loan, he was sent to Arsenal for €5.8 million last summer.
24. Tanguy Ndombele, MF, Tottenham Hotspur
Signed from Lyon for €62 million, 2019-20
Everything about this signing seemed right. Spurs had just made the Champions League final, and it was time to splash some cash for an exciting up-and-comer; Ndombele had just produced a career-high seven assists while helping Lyon to a third-place finish in Ligue 1, and he had attracted interest from virtually every major club. Spurs landed him for a club-record fee, and he … just never had it.
Few among Spurs’ assembly line of managers were impressed enough to give him major minutes, and when he saw the pitch he didn’t do much with the opportunities. In three seasons and more than 5,000 minutes in all competition, he produced just nine assists, and he has served as a journeyman reserve for most of the time since his departure.
23. Eliaquim Mangala, CB, Manchester City
Signed from Porto for €45 million, 2014-15
Mangala was the most expensive transfer yet in the City Group’s ambitious building plan, though he most certainly didn’t play like it. Acquired at the age of 23 after an excellent 2.5-year audition at Porto, Mangala just never found his lane. He was a part-time starter for two seasons under Manuel Pellegrini, but he wasn’t at all what new manager Pep Guardiola was looking for starting in 2016-17. He was loaned out twice and started only four league matches for Guardiola.
22. Rasmus Hojlund, CF, Manchester United
Signed from Atalanta for €77.8 million, 2023-24
Just as Fergie-era United had plenty of guys on the Best Transfers list, post-Fergie United has plenty of players on this list. And moving for Hojlund was a pretty good microcosm of the problems. United dramatically overpaid for a 20-year-old who had just scored nine league goals for a prolific Atalanta side (he averaged a goal every 189.4 minutes); after just two years and a goal every 246.4 minutes, he was already on the “he’s unsalvageable, let’s start loaning him out” list. Overpay, then give up on a guy quickly — that’s not the best way to invest.
21. Mario Balotelli, FW, Liverpool
Signed from AC Milan for €20 million, 2014-15
From Ian Graham’s How to Win the Premier League, about his time working at Liverpool:
“Balotelli’s past behaviour raised some red flags, but perhaps we could mitigate the risks. At the time Liverpool used the services of a psychologist, Steve Peters. If we could get an expert opinion on Balotelli from a psychologist, we could be more comfortable with the signing, or decide against it. But Steve would not interrupt his holiday to talk to Balotelli. Instead, Brendan [Rodgers] met him at Melwood and the meeting went very well. Maybe it would work out…”
It did not, in fact, work out. Balotelli was still only 24 years old and had produced double-digit league goals in three straight seasons (one at Manchester City, two at Milan). His problematic past behavior kept the price tag down a little bit, too. But by December, he was getting suspended because of controversial social media behavior, and he didn’t score his first league goal until February. He was loaned back to Milan the next season, before leaving on a free transfer after just two years.
20. Andy Carroll, FW, Liverpool
Signed from Newcastle United for €41 million, 2010-11
On deadline day in late January 2011, Liverpool made two moves intended to change the trajectory of the club. One was for Luis Suárez, who nearly led Brendan Rodgers’ Reds to a Premier League title in 2013-14 and eventually became part of the best Barcelona squad of all time in 2014-15. The other was Carroll, a 6-foot-3 headers king who was an early love of the analytics community and would take the No. 9 jersey from a departing Fernando Torres.
Carroll was the most expensive British player to date (in terms of transfer fee) and had scored 11 goals in his first Premier League campaign with Newcastle. But he would score only six goals in two league seasons at Anfield. Rodgers never wanted him and never figured out a place for him, and he was sent to West Ham for less than half his original fee.
19. Bebe, MF, Manchester United
Signed from Vitoria Guimaraes for €8.8 million, 2010-11
From Sir Alex Ferguson’s 2013 autobiography:
“Bebe is the only player I ever signed without first seeing him in action. We have a good scout in Portugal who had flagged him up. This boy had been playing homeless football and became a triallist for a second division team. He did really well. Our scout told us, ‘We need to watch him.’ Then Real Madrid were on his tail. I know that’s true because Jose Mourinho told me Real were ready to sign him and that United had jumped in front of them. We took a wee gamble on it.”
Even when you’re potentially the best manager of all time, gambles don’t always pay off. Granted, the competition would be far stiffer now, but 10 years ago Bebe was voted Manchester United’s biggest flop by a comfortable margin. What he lacked in a major transfer fee, he made up for with an almost total lack of production. In fact, he made just seven total appearances for United, two in the Premier League.
18. David Bentley, RW, Tottenham Hotspur
Signed from Blackburn for €22 million, 2008-09
Bentley claimed that a three-year stint with Blackburn — including a two-year run in which he produced 10 league goals and 16 assists — had rekindled his love of the game; it also earned him a spot on the national team. It was a big deal when he moved to Tottenham, but in parts of three seasons he played the equivalent of 32.4 90s and recorded all of two goals and three assists. He battled knee injuries, produced nothing on a series of loans and retired at age 29, his love of the game re-extinguished.
17. Andriy Shevchenko, FW, Chelsea
Signed from AC Milan for €43.9 million, 2006-07
Another record signing who couldn’t clear a ridiculously high bar, Shevchenko also had the added burden of being Andriy Shevchenko, the 2004 Ballon d’Or winner, 2003 Champions League winner and scorer of 173 goals in seven seasons at Milan. It took a British record fee for Abramovich to lure the long-sought Shevchenko to Chelsea and, well, there’s a reason why you don’t pay record fees for a guy who’s about to turn 30.
Injuries eventually held the Ukrainian star back, but he had not really ever gotten going in the first place. He scored 22 goals in 77 appearances with the club — not bad, but not Ballon d’Or worthy. He was back in Milan by 2008-09.
16. Winston Bogarde, CB, Chelsea
Signed from Barcelona on a free transfer, 2000-01
Step one: The 29-year-old Bogarde signs as a favorite of manager Gianluca Vialli, offsetting a nonexistent transfer fee with a mammoth-for-its-day salary.
Step two: Vialli is almost immediately fired, and successor Claudio Ranieri has no interest in playing the risk-taking defender. Chelsea, beset by precarious pre-Abramovich finances, decide to only loan him out if someone is willing to pay the salary.
Step three: No one pays the salary, and despite pressure from Chelsea to agree to a different contract, he holds strong, takes his paychecks for four years and retires after just nine total appearances for the club. That’s a success story if you squint just right, but it certainly wasn’t a success for Chelsea.
15. Dani Osvaldo, FW, Southampton
Signed from Roma for €15.1 million, 2013-14
Honestly, Southampton have enjoyed solid success over the Premier League’s history considering some of the poor investments they’ve made. A year after their ill-fated move for Gaston Ramirez, they brought in Osvaldo as their record signing despite some pretty clear warnings. Osvaldo had seen success under the Saints’ then-manager Mauricio Pochettino, but he had also recently been suspended for punching Erik Lamela in the face. (Lamela was his Roma teammate at the time.) It wasn’t a surprise when he scored a couple of goals early in 2013-14, but it couldn’t have been a total surprise when he got into scraps with first an opponent in December, then teammate José Fonte in January. He was loaned out later that month, and remained on loan until transferring out in 2015.
14. Steve Marlet, FW, Fulham
Signed from Lyon for €17.6 million, 2001-02
Marlet was 26 years old and coming off of a lovely 12-goal, five-assist season for Lyon; it makes sense that he would have commanded a solid transfer fee. But he was the third-most expensive transfer in the league that season — more expensive than Robbie Fowler (€16.8 million to Leeds), Frank Lampard (€16 million to Chelsea), or Giovanni van Bronckhorst (€13.5 million to Arsenal). If you find that odd, so, too, did Fulham owner Mohamed Al Fayed, who accused manager Jean Tigana of benefiting financially from the deal. Marlet produced 11 league goals and four assists in two seasons before moving on to better things at Marseille, but “so questionable that the owner went to court about it” certainly assures a high ranking here.
13. Wesley Fofana, DF, Chelsea
Signed from Leicester City for €80.4 million, 2022-23
In what was supposed to be a transformative season of moves after BlueCo’s acquisition of Chelsea from Abramovich, the Club brought in 15 new transfers for a combined €616.3 million; we can argue whether players like Enzo Fernández (€121 million) or Marc Cucurella (€65.3 million) have lived up to their massive fees, but they’ve at least become strong contributors. Others commanded solid resale fees when they were pushed back out the door.
But while Fofana wasn’t the single worst addition of this window — we’ll get to another one soon enough — sending Leicester City more than €80 million for a center back set an impossibly high bar, especially for someone who had missed much of the previous season with injury and had dealt with a series of knee issues through the years. Fofana’s been hurt nonstop and missed a year with an ACL tear. He’s made just 57 appearances in parts of four seasons.
12. Bosko Balaban, CF, Aston Villa
Signed from Dinamo Zagreb for €7.8 million, 2001-02
It just takes water a while to find its proper level sometimes. By his mid-20s, Balaban had become a routinely successful striker in Belgium and Croatia, averaging 16.2 goals per season in all competitions over a six-year span. But moving from Dinamo Zagreb to Aston Villa at age 23 was too much, too soon. Balaban’s transfer fee was equivalent to a team paying €30-40 million today, but after scoring 19 goals for Dinamo Zagreb in 2000-01 (plus five goals for the Croatian national team in 2001), he was a nonentity in Birmingham, making only eight appearances, scoring zero goals, and disappearing back to Zagreb by the next season.
There was something in the water at the turn of the century — five signings from 2001-02 made this list, tied with 2022-23 for the most of any season — but the move for Balaban was a standout for all the wrong reasons.
11. Alexis Sánchez, FW, Manchester United
Signed from Arsenal for €34 million (and a swap for Henrikh Mkhitaryan), 2018-19
It appeared Sanchez was set to move to Manchester City when United swooped in and lured him away with a preposterous salary offer. Considering what he had produced at Arsenal — an average of 17.7 goals and 7.3 assists in the Premier League over his last three full seasons — this was seen as an absolute coup. But at a time when pretty much anyone moving to Old Trafford was struggling to meet even average expectations, Sanchez came nowhere close. Injuries were an issue, and he scored just three goals in 32 league appearances.
Within a year and a half, United was paying half his salary while loaning him to Inter Milan, where he would move on a free transfer soon after.
10. Kalvin Phillips, DM, Manchester City
Signed from Leeds United for €49 million, 2022-23
It made so much sense in theory. Phillips was an important piece for Marcelo Bielsa during Leeds’ promotion push (and initial Premier League success), and he was used to doing some decent destroyer work in transition defense – something that has certainly dragged City down at times. But he had battled injury issues for a decent portion of 2021-22, and he injured his shoulder almost immediately after moving to Manchester. It seemed like he never got up to speed after that. He’s made a total of 32 appearances for the club in 3.5 seasons, and he’s been loaned out for much of that time.
9. Tomas Brolin, MF, Leeds United
Signed from Parma for €5.3 million, 1995-96
Five million Euros was still a pretty hefty fee in the mid-1990s — a club record at the time for even an ambitious club like Leeds — but Brolin was coming off of a serious ankle injury when he came aboard (and arrived quite a bit heavier than expected), and he rebelled when manager Howard Wilkinson asked him to play out of position, deliberately playing poorly in a loss to Liverpool. That was pretty much the end of that. He was loaned out over the next couple of seasons, played briefly for Crystal Palace and retired by age 28.
8. Jadon Sancho, RW, Manchester United
Signed from Borussia Dortmund for €85 million, 2021-22
Your environment evidently matters a lot. In parts of four seasons with Borussia Dortmund (almost all before his 21st birthday), Sancho averaged 0.98 combined goals and assists per 90 minutes. He was one of the brightest young stars in the world and had made 23 national team appearances before he turned 22. But at Manchester United, he never made even a hint of an impact, averaging just 0.32 goals and assists per 90. He was loaned back to Dortmund and helped to lead BVB to the Champions League final; then he returned to Manchester and made no impact. Two more years have brought about two more loans.
7. Romelu Lukaku, CF, Chelsea
Signed from Inter Milan for €113 million, 2021-22
Lukaku is another poster child for both “Your environment matters” and “Some people only find themselves in Italy.” Despite injuries slowing him down at times, Lukaku has remained a solid goal-scorer into his 30s. Just not with Chelsea.
Acquired after scoring 64 goals in two years with Inter, the Belgian star, who had bailed for Italy when a stay at Manchester United went sour, scored just 15 times in 44 appearances with the Blues in 2021-22, with constant pressure and endless negative headlines, Lukaku was miserable enough that he was basically begging to be loaned out. He spent 2022-23 with Inter (14 goals) and 2023-24 with Roma (21 goals), then moved permanently to Napoli in 2024.
6. Ricky Alvarez, MF, Sunderland
Signed from Inter Milan for €10.5 million, 2015-16
A solid contributor for Inter — he had four league goals and eight assists in 2013-14 — Sanchez arrived on loan with an agreement that, if Sunderland didn’t get relegated that season (and if he didn’t suffer any further issues with a problematic left knee), they would acquire him permanently for the €10.5 million fee. Only, he barely played that season because of an issue to his right knee, and when they narrowly survived relegation, Sunderland tried to get out of the mandatory transfer arrangement.
They failed … and they also didn’t offer him a new contract, meaning they spent €10.5 million on a player who immediately left for Sampdoria. Whoops.
5. Danny Drinkwater, CM, Chelsea
Signed from Leicester City for €37.9 million, 2017-18
Having just won a Premier League title with a lineup that was half-full of starters aged 28 or older, Chelsea used the summer of 2017 to transform themselves. They didn’t get what they paid for. Forward Álvaro Morata (€66 million) would score just 16 league goals in two seasons, midfielder Tiemoue Bakayoko (€40 million) started for one season and then became an annual loanee, midfielder Davide Zappacosta (€25 million) started 13 total league games, and left back Emerson (€20 million) started 23.
Still, Drinkwater was comfortably the most disappointing newcomer of the bunch, playing 1,182 minutes in all competitions with one goal, zero assists, just 12 chances created and four loan spells over five seasons. His contract was long and expensive, and he dealt with both injuries and a number of off-the-pitch problems. This was bad in every way a signing can be bad.
4. Ali Dia, FW, Southampton
Signed on a free transfer, 1996-97
Take it away, Bill Barnwell:
“The Dia story feels as if it comes from another universe. A man calls Southampton manager Graeme Souness pretending to be World Player of the Year George Weah. The purported Milan striker recommends Dia, his cousin, suggesting he had just scored two goals for Senegal the prior week and had 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 soccer.
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 soccer, never to return. […]
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 soccer player, let alone actually getting him onto the pitch. … 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.”
3. Nicolas Pépé, RW, Arsenal
Signed from Lille for €80 million, 2019-20
After an excellent 22-goal, 11-assist season for Lille in 2018-19, there was no doubt that big names would come after Pepê. After a while, however, it sure felt like Arsenal was negotiating against itself. And in a summer full of preposterous European signings — João Félix to Atletico for €127 million, Antoine Griezmann to Barcelona for €120 million, Harry Maguire to Manchester United for €87 million (which would have made this list if it were a top 100) — Pepe’s move became one of the biggest.
Except … he produced just 43 Premier League starts and 16 goals in three seasons. Inflated expectations, problems with authority and massive inconsistency were all issues, and after four years he left for Trabzonspor in Turkey on a free transfer.
2. Antony, RW, Manchester United
Signed from Ajax for €95 million, 2022-23
The 2022-23 season occupies four of the top (well, bottom) 13 on this list. Antony’s move was both the second-worst of that summer and, potentially, the second-worst of the Premier League’s existence. Transfermarkt’s market value figures are crowd-sourced estimates and don’t provide any actual, real-life guidance, but you’ll rarely see an overpay more stark than this one. Antony was valued at €35 million when United, having just hired Ajax’s Erik ten Hag, paid nearly three times that figure for the burgeoning Ajax star, who had enjoyed two solid, but not quite spectacular, campaigns in the Eredivisie.
What did €95 million buy them? Five league goals and 38 starts (and a series of domestic assault allegations) in parts of three seasons before a loan and, eventually, a €22 million move to Real Betis.
1. Mykhaylo Mudryk, LW, Chelsea
Signed from Shakhtar Donetsk for €70 million, 2022-23
In the first half of the 2022-23 season, Mudryk combined 10 goals with eight assists for Shakhtar Donetsk in the Champions League and the Ukrainian Premier League. In the more than three years since, he has produced 10 goals and six assists in all competitions. His production was seen as disappointing from the start, and now he hasn’t played at all since November 2024 because of doping charges.
Chelsea outdueled Arsenal in a desperate race for the 21-year-old’s services and signed him to a massive, 8.5-year deal, a customarily exaggerated length common to most deals in the early days of BlueCo’s ownership. You can’t say this was a case of a club negotiating against itself, as with some other deals on this list, but by whatever standard you want to use — dollars spent per goal scored? re-sale value? — they haven’t benefited even slightly from the signing.
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