Rating The Top 10 Most Expensive Premier League Signings Ever (Flop or Not)

Published on 9 August 2023 at 20:00

The Premier League is the financial powerhouse in modern football, and outside of Real Madrid and Barcelona, THE place to be for many aspiring talents and established names. Particularly in the last decade clubs have spent tens of millions of pounds to bring megastars in the making into their squads, and for every one that succeeds, it seems like there’s always one destined to be a failure. 


We’re going to be looking at the top 10 most expensive players in Premier League history, and evaluating whether or not they were a success, a flop, or if the jury’s still out on their value. From World Cup winning midfielders to esteemed journeymen, this is our official ranking. 


For the sake of clarity, we won’t be including any signings made in the 2023/24 Summer window, and using Transfermarkt’s value when listing these players. 


1) Enzo Fernandez: Jury’s Out 

Fresh off an immense World Cup campaign with Argentina, where he scooped not only the Jules Rimet but also the Young Player of the Tournament award, Enzo Fernandez’s departure from Benfica to the Premier League felt like a matter of when, rather than if.  


It’s just a shame that he joined a tumultuous Chelsea side in the midst of their worst season in recent memory. This upcoming season affords Fernandez a real opportunity to showcase his technical ability, playing under a more stable manager and system with Mauricio Pochettino, although Chelsea’s severe lack of defensive and attacking coverage in midfield could stretch Fernandez out too far for him to succeed. 


2) Jack Grealish: Success 

A club tenure of two halves, where one has dramatically outshone the other. 


Jack Grealish just couldn’t find his footing in his first season in Manchester, being nothing but a background character to City’s narrow title victory. His second season however, like many a player under Pep Guardiola’s coaching, was like watching a player reborn. 


As dangerous and creative as ever, including particularly astounding performances against Liverpool and Real Madrid, saw Grealish become a major player in the Cityzens’ treble winning side, and locking down that coveted LW position. 


3) Romelu Lukaku: Flop (Chelsea)

Spoiler alert: this won’t be the first time you read Lukaku’s time on this list.  


Having shown he was still as prolific as ever for Inter Milan and his native Belgium, Chelsea re-signed Lukaku in the hopes of finally breaking their no.9 curse that has plagued strikers there since Didier Drogba’s first departure. 


After a promising start, things drastically fell apart, with calamitous errors and repeat blank appearances for Lukaku culminated in an infamous interview with Sky Italia, where he advocated for his return to Italy and away from his current employers.  


Having now found himself on the wrong side of Inter Milan’s team selection, and with Juventus looking like the only salvation for his career (and Chelsea’s bank balance), Lukaku’s second stint at Chelsea is an unprecedented failure that could still somehow get worse. 



4) Paul Pogba: Flop


On his day, Paul Pogba was truly a top 5 player in the world, and arguably the most gifted midfielder of his generation.


It’s just a shame the majority of those days came for his country, and when they did come in the red of Manchester United, they were few and far in between.  


At one point the most expensive transfer of all time, Pogba may have scooped the Europa League and generated some iconic performances during his stay in the Premier League, but the fact he eventually left on a free meant his value and overall contribution to Manchester United left much to be desired. 


5) Antony: Flop  


Although still young and adapting to the Premier League, Antony has certainly failed to live up to the price tag Manchester United found themselves paying Ajax for his services.


Delivering highlights reels in the Eredivise and Champions League on a regular basis, the talented Brazilian has failed to make a solid impression in his first season in England. Frequent attitude problems on the pitch and inconsistent performances, he looks to be one of the very few things Erik ten Hag has got wrong so far in the Dutchman’s spell as Manchester United boss.


6) Harry Maguire: Flop 


Is Harry Maguire’s record-breaking transfer to Manchester United the worst ‘big’ signing in football history?


Fresh off some great performances for Leicester and the England National Team, where he became a minor cult hero following the Three Lions’ run to the semi-finals, he was widely expected to be the beating heart of a resurgent Manchester United team.


What’s ensued is calamitous performance after calamitous performance after calamitous performance. Subtle digs from teammates, lambasting within the media, even as club captain dropped entirely by his incumbent manager. 


Now looking at a £40-50m loss just to get him off the squad’s books, Maguire at Manchester United is the epitome of a football transfer disaster. 


7) Jadon Sancho: Flop 

Arriving from Borussia Dortmund with stats comparable to the likes of Lionel Messi, Sancho was expected to set the Premier League ablaze in 2021 and for years to come. 


Instead, what made Sancho so exciting to watch in the Bundesliga seems to have instantly disappeared the moment the youngster’s feet first touched the grass at Carrington. 


Gone is the player who would routinely skim past defenders like they were invisible, instead Sancho has become a far more timid, cautious footballer who was a shell of the prodigal winger he looked to be.


8) Romelu Lukaku: Jury’s Out (Man Utd)

The only player with the distinction of being on this list twice, you would be hard pressed to find any other player who seems to have alienated and irritated every fanbase he’s been played in front of (except maybe Michael Owen).


After an admittedly fantastic run of form with West Brom and Everton, Lukaku was tapped to be the next great striker at Manchester United, but with the benefit of hindsight, we should’ve seen Lukaku failing to live up to expectations properly from the very beginning.


There were bright sparks however: his most notable contribution in Man Utd’s colours came against PSG in the Champions League, launching a notable comeback at the Parc des Princes. But his quick departure to Inter Milan only seems to highlight a major problem with Manchester United and their talent acquisition, as well as Lukaku’s drive to consistently perform for the team paying the big money for him.

9) Virgil Van Dijk: Success 

One of the greatest signings in Premier League history, Virgil Van Dijk simply transformed Liverpool from aspiring top 4 hopefuls into one of the most formidable teams in the league’s 30+ year history.


One of the key players brought in after Coutinho’s departure (which legend says is still being used to justify Liverpool signings to this day), Van Dijk has gone on to become arguably the best defender in world football, helping Liverpool win that elusive first Premier League title and even put himself in Ballon D’or contention. Defending, goals, leadership, prime Virgil Van Dijk could simply do it all. 


10) Wesley Fofana: Flop 

Much like Antony and Sancho, there’s still plenty of time for Fofana to recover from his current slump and become the defender he’s being hyped to be. But in his case, it’s not bad form that’s affecting him, just terrible luck.


Onto yet another major injury at just 22-years-old, Chelsea have already lined up arguably superior backup options in compatriots Disasi and Badiashile, as well as the highly-rated Levi Colwill. Expect to see Fofana depart the club in the near future in a desperate attempt to recoup some of his mammoth transfer fee and potential. 


Image Credit- Дмитрий Голубович

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