Every season, Premier League clubs break records with eye-watering transfer fees, hoping their latest superstar signing will deliver trophies, goals, and unforgettable moments. Some of these big-money moves shape football history, while others turn into costly mistakes that haunt clubs for years.
As we move deeper into 2025, some of the league’s most expensive transfers are still making headlines, whether for the right or wrong reasons. With new transfer records expected to be shattered in the next window, now is the perfect time to look back at the Premier League’s priciest signings and ask the big question: Were they worth it?
The Hits: When Big Money Was Well Spent
Some signings came with huge expectations and somehow have exceeded them, helping their teams win titles, break records, and dominate the league.
Declan Rice (Arsenal – £105m, 2023)
Arsenal’s decision to break their transfer record for Declan Rice raised eyebrows, but two seasons later, it’s looking like a masterstroke. A leader in midfield, Rice has been instrumental in Arsenal’s Premier League and Champions League ambitions, proving he’s worth every penny.
Jack Grealish (Manchester City – £100m, 2021)
After a slow first season, Grealish silenced critics by helping Man City win the 2022/23 treble. His performances in big games, especially in City’s Champions League-winning run, justified the investment.
Erling Haaland (Manchester City – £51m, 2022)
While not one of the most expensive transfers on this list, Haaland’s impact has been historic. Breaking goal-scoring records in his first Premier League season, he played a crucial role in City’s 2022/23 treble-winning campaign. When it comes to value for money, Haaland might be the best signing of the decade.
Virgil van Dijk (Liverpool – €84m, 2018)
Critics questioned Liverpool’s decision to make Van Dijk the most expensive defender in history, but he proved to be the missing piece in their puzzle. His arrival transformed their defence, leading to Champions League and Premier League glory.
Kevin De Bruyne (Manchester City – £55m, 2015)
Few signings have shaped a club’s success like De Bruyne at City. The Belgian midfield maestro has been at the heart of their dominance, winning multiple league titles and setting assist records.
The Misses: When Big Transfers Flopped
Not every expensive signing delivers. Some fail to adapt, struggle with injuries, or simply don’t justify their price tag.
Romelu Lukaku (Chelsea – £97.5m, 2021)
After excelling at Inter Milan, Chelsea’s record signing was expected to be the missing piece in their attack. Instead, Lukaku’s return was a disaster falling out with the manager, struggling for consistency, and getting loaned back to Italy.
Jadon Sancho (Manchester United – £73m, 2021)
Once seen as one of the brightest young talents in Europe, Sancho’s move to United never lived up to expectations. After struggling for form and clashing with Erik ten Hag, he was sent back on loan to Borussia Dortmund in 2024.
Paul Pogba (Manchester United – £89m, 2016)
Signed for a world-record fee at the time, Pogba’s second stint at United was full of flashes of brilliance but overall inconsistency. Injuries, tactical struggles, and off-field issues meant he left on a free transfer in 2022, making it one of United’s most frustrating transfers.
Nicolas Pépé (Arsenal – £72m, 2019)
Pépé arrived as Arsenal’s most expensive player ever, but never fully adapted to the Premier League. By 2023, he had left on a free transfer, making his signing a costly mistake for the Gunners.
As we look ahead to the next transfer window, clubs are once again preparing to spend big. But will the next record-breaking signing be a game-changer or another expensive regret?
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