The Most Expensive Transfer Flops in Football History

In the world of football, big money transfers often make headlines, generating immense excitement among fans and raising expectations for success. However, the beautiful game is not immune to the occasional disappointment, as history has shown us with several high-profile transfer flops. In this article, we delve into the realm of shattered dreams and broken promises, highlighting the most expensive transfer flops in football history.

1. Philippe Coutinho: Liverpool – Barcelona (2018)

Considered one of Liverpool’s most significant transfers but ultimately the worst for Barcelona. The Catalan club agreed to pay €120m (£100m/$130m), with the potential for an additional €40m (£34m/$43m) in bonuses, for a player they didn’t actually require. Whether Coutinho was an attacker, midfielder, or something in between seemed unclear to Josep Maria Bartomeu, yet he still made the effort to sign the Brazilian. Throughout his four-year tenure at Barcelona, Coutinho’s notable contribution was scoring two goals against his own team while on loan at Bayern Munich in 2020. After multiple attempts to offload him, Barcelona finally let him join Aston Villa in 2022 for a mere €20m (£17m/$21.5m) as part of their desperate financial recovery following Bartomeu’s near bankruptcy the club.

2. Eden Hazard: Chelsea – Real Madrid (2019)

Eden Hazard’s long-awaited move to Real Madrid from Chelsea was marred from the beginning when he arrived for pre-season training overweight. Unfortunately, injuries plagued the Belgian winger, who had previously enjoyed a relatively injury-free spell at Chelsea. Even when he managed to play a series of games in Spain, he failed to live up to the standards he had set during his seven-year tenure in the Premier League, appearing as a poor imitation of his former self. Despite winning significant trophies, including the Champions League, Hazard’s contribution to Real Madrid’s 2021-22 triumph was minimal, akin to Gareth Bale’s involvement. Notably, Hazard’s Real Madrid career concluded without him playing a single minute in a Clasico, a testament to his status as the worst signing in the club’s history.

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3. Harry Maguire: Leicester City – Man Utd (2019)

Harry Maguire proved himself as a competent Premier League defender during his time at Leicester City. In fact, his abilities attracted interest from the likes of Pep Guardiola and Manchester City in 2019. While Maguire claims he chose Manchester United over their rivals, the truth is that Manchester City deemed the price too high for a defender and decided against the move. Ultimately, their judgment was proven correct. Maguire has faced severe criticism from Manchester United fans over the past three years, with some crossing the line in their abuse towards him. His time at Old Trafford has been bitterly disappointing, and the decision to appoint him club captain has been overshadowed by a series of dismal performances and notable errors that have become fodder for memes. Manchester United originally paid £80m ($100m) for Maguire, but they are likely to receive less than half of that amount when they eventually sell him this summer. While he may not be as terrible as Rafael van der Vaart once claimed, the English international stands as a colossal waste of money.

4. Paul Pogba: Juventus – Man Utd (2016)

In 2012, Manchester United lost Paul Pogba for nothing. A decade later, history repeated itself. While many fans were happy to see a player who had failed to consistently showcase his undeniable world-class quality leave the club, losing such a valuable asset for no fee still hurt. United had originally re-signed Pogba from Juventus in 2016 for a world-record sum of £89.5m. However, after six seasons, which included winning the Europa League and Carabao Cup, his performances were often lackluster, and he made public statements that hinted at a desire to join other clubs. Eventually, Pogba returned to Juventus, much to the relief of most fans.

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5. Romelu Lukaku: Inter – Chelsea (2021)

When Romelu Lukaku returned to Chelsea, he expressed a desire to complete unfinished business after failing to score during his previous stint at Stamford Bridge. However, his second spell at the club turned out to be worse than the first. Despite finishing the 2021-22 season as the team’s top scorer, Lukaku’s overall performance was disappointing, considering the club had invested a record-breaking £97.5m ($119m) in acquiring his services. Lukaku must shoulder part of the blame himself for conducting an unauthorized interview with Sky Sport Italia during the season, where he professed his love for his former club Inter and, astonishingly, criticized Thomas Tuchel’s tactics. Losing the trust of his coach and the support of the club’s fans proved detrimental, leading to his inevitable return to San Siro on loan.


The world of football is not immune to expensive transfer flops, as these examples illustrate. Whether it’s a lack of adaptation, injuries, or simply the inability to meet the immense expectations that come with a hefty price tag, the history of the game is littered with cautionary tales. However, it’s important to remember that in football, success is not always guaranteed, even for the most talented players.