Top Premier League's Worst Signings of All Time |

Money is both the fuel and the curse of modern football. With television deals swelling club coffers and billionaire owners eager to leave their mark, transfer windows have become arenas of reckless spending.

And while the Premier League has been home to some of the best signings in football history, it has also given us some of the most disastrous.

Every supporter remembers that sinking feeling when their club unveils a marquee signing, only for the player to flop in the most dramatic way possible.

Sometimes the failure comes from injuries. Sometimes it’s the wrong fit.

Other times, it’s pure mismanagement. Whatever the reason, the Premier League has produced more than its fair share of costly mistakes.

For this list, four factors define a disastrous signing: transfer fee, expectation, performance on the pitch, and longevity. A bad mark in one area might be forgivable. Fail in all four, and you make this list.

Here are the 20 worst signings in Premier League history.

Contents

17. Danny Drinkwater — £34.1m to Chelsea

17. Danny Drinkwater — £34.1m to Chelsea

Top Premier League's Worst Signings of All Time

Fresh from Leicester’s miracle title win, Drinkwater earned a big-money move to Chelsea in 2017. It was the beginning of the end for his career.

He barely featured, falling out of favour with multiple managers.

Off the pitch, reports of partying and a lack of professionalism didn’t help. He made just 12 league appearances in five years, an astonishingly poor return for such a large fee.

Drinkwater later admitted that the move ruined his career.

16. Jack Rodwell — £11.3m to Sunderland

Few players symbolize a club’s decline like Jack Rodwell at Sunderland.

Signed in 2014 after spells with Everton and Manchester City, Rodwell arrived as a midfielder who still had time to kick on in his career. Instead, he became the face of Sunderland’s collapse.

He collected huge wages, reportedly £70,000 a week, while contributing almost nothing on the pitch.

By the time Sunderland were relegated from the Premier League and then the Championship, Rodwell was barely playing but still draining resources.

He became so unpopular that fans booed his name when it appeared on the teamsheet. His time at the Stadium of Light was later immortalised in Netflix’s Sunderland ‘Til I Die, sealing his place in Premier League flop folklore.

15. Nicolas Pépé — £72m to Arsenal

When Arsenal smashed their transfer record to bring in Nicolas Pépé from Lille in 2019, fans expected fireworks. His performances in France had been dazzling, and £72 million was supposed to secure a winger who could light up the Premier League.

Instead, Arsenal got a player who was sometimes dangerous but too often anonymous.

His tally of 16 league goals in three seasons is not terrible, but when you break the bank for a forward, you expect more than flashes of ability.

He never became the game-changer Arsenal needed and eventually left with the sense of a wasted opportunity.

Pépé wasn’t awful, but for that price, “decent” is nowhere near good enough.

14. Tanguy Ndombele — £63m to Tottenham

Tottenham supporters still wince at the mention of Tanguy Ndombele. Signed in 2019 for a club-record £63 million, he had everything in his locker: power, flair, creativity. But talent only takes you so far, and Ndombele never matched his ability with the required attitude.

Managers grew frustrated with his fitness and lack of work rate.

He drifted through games and often seemed disinterested. Despite occasional flashes of brilliance, he was eventually pushed out on loan multiple times before leaving without Spurs recouping anything close to their investment.

For a club not known for splashing the cash, his signing remains one of their expensive missteps.

13. Ángel Di María — £67.5m to Manchester United

On paper, Ángel Di María should never be on a list like this.

He’s a world-class winger with Champions League pedigree and a glittering international career. Yet his brief spell at Manchester United in 2014–15 is one of the most infamous flops of the modern era.

He started brightly, winning Player of the Month in his first weeks, but an injury derailed him.

He never recovered his rhythm, and off-field problems—including an attempted burglary at his home – made life in Manchester miserable.

Within a year, he was offloaded to Paris Saint-Germain. His failure wasn’t about talent, but he remains a glaring example of money wasted in the Premier League.

12. Kepa Arrizabalaga — £71.8m to Chelsea

Chelsea’s desperation in 2018 led to the most expensive goalkeeper in football history.

At £71.8 million, Kepa was supposed to be the long-term replacement for Thibaut Courtois. Instead, he became a cautionary tale.

The infamous Carabao Cup final incident, when he refused to be substituted despite his manager’s instructions, symbolised his arrogance and the breakdown of trust.

He never looked commanding between the sticks, often spilling routine saves or positioning himself poorly. Chelsea eventually loaned him out, with little chance of ever recouping their investment.

11. Andriy Shevchenko — £39.5m to Chelsea

One of the greatest strikers of his generation, Andriy Shevchenko was a Ballon d’Or winner and a lethal force at AC Milan. But when he joined Chelsea in 2006 for what was then a British transfer record, he left his best years behind in Italy.

Tasked with dislodging Didier Drogba, Shevchenko never found his feet.

He managed just nine league goals in three years, often looking lost in the physical chaos of English football.

His time at Stamford Bridge was a shadow of his previous brilliance, making him one of the most disappointing marquee signings in Premier League history.

10. Jean-Kévin Augustin — £15.5m to Leeds United

Jean-Kévin Augustin barely touched the ball for Leeds United, but his story is unforgettable.

Signed on loan from RB Leipzig in January 2020 with an obligation to buy if Leeds won promotion, the move seemed harmless at first.

Then the pandemic delayed the season. Leeds argued that the obligation to buy should no longer apply, but FIFA ruled against them.

The result: Leeds had to pay £15.5 million for a player who made just three substitute appearances, totalling 48 minutes on the pitch.

It was money set on fire, a reminder that fine print in contracts can be just as costly as a bad player.

9. Bebé — £7.9m to Manchester United

Even Sir Alex Ferguson wasn’t immune to a transfer disaster.

In 2010, he signed Bebé, a Portuguese forward who had never played above his country’s third tier. Ferguson admitted he had never seen him play and relied on a recommendation. It was a gamble that failed spectacularly.

Bebé looked out of his depth from the start. In four years, he played just two league games, scoring no goals and offering nothing close to the standard required at Old Trafford.

United could absorb the financial hit, but the signing became a running joke among rival fans and remains Ferguson’s biggest transfer blunder.

8. Alexis Sánchez — £35m + Henrikh Mkhitaryan to Manchester United

Alexis Sánchez was brilliant at Arsenal. When Manchester United swooped in 2018, swapping Henrikh Mkhitaryan for him and paying astronomical wages, it felt like a coup. Instead, it was a catastrophe.

Sánchez looked like a shadow of his former self, managing just three league goals in two-and-a-half years.

The real damage came off the pitch: his wages were so inflated that they disrupted United’s pay structure and morale.

In the end, both clubs lost out, but United’s side of the deal was a financial and sporting disaster.

7. Wesley Fofana — £75m to Chelsea

Chelsea’s spending under Todd Boehly is legendary for its chaos, and Wesley Fofana stands out as one of the biggest gambles gone wrong.

When Chelsea paid Leicester £75 million in 2022, they were buying what looked like one of the best young defenders in the league. But the warning signs were already there. Fofana had a history of serious injuries, and those concerns only worsened in London.

Injuries have robbed him of consistency, rhythm, and confidence.

Across three seasons, he’s barely passed 30 league appearances. The fact that Chelsea made him one of the most expensive defenders in football history only deepens the sense of failure.

At 24, he still has time, but right now, his time at Stamford Bridge looks like one of the most wasteful deals the league has ever seen.

6. Romelu Lukaku — £97.5m to Chelsea

Romelu Lukaku’s second spell at Chelsea was supposed to be his redemption arc. Instead, it was another chapter of disappointment.

Signed for a club-record fee in 2021, Lukaku started brightly but quickly unravelled.

A lack of fitness, poor chemistry with teammates, and a bombshell interview where he admitted he wasn’t happy at the club sealed his fate.

Scoring just eight league goals in his only full season, he became another name on Chelsea’s long list of failed striker experiments.

5. Jack Grealish — £100m to Manchester City

At £100 million, Jack Grealish became the most expensive British player ever when he left Aston Villa for Manchester City in 2021. For a player who had carried Villa on his back, expectations were sky-high.

While he contributed to City’s treble in 2023, his individual performances fell flat in the years that followed.

Four goals across two seasons is not what you expect for a nine-figure fee.

Grealish wasn’t a disaster in the way others on this list were, but for that price, his lack of consistency makes him one of the most underwhelming signings in league history.

4. Mykhailo Mudryk — £89m to Chelsea

Chelsea’s January 2023 capture of Mykhailo Mudryk felt like a statement. They hijacked Arsenal’s move and handed the Ukrainian winger an eight-year contract.

What followed was chaos.

Mudryk’s raw pace was exciting, but his end product was dreadful.

Few goals, few assists, and countless frustrating performances made fans wonder what the club had seen in him. His provisional suspension in 2024 for testing positive for a banned substance only deepened the disaster.

With so much money tied up in the deal, his signing has become an anchor around Chelsea’s neck.

3. Jadon Sancho — £73m to Manchester United

United had chased Jadon Sancho for years, and when they finally landed him in 2021, fans believed they had secured one of Europe’s best young attackers.

Instead, they got inconsistency, poor attitude, and public feuds with the manager.

Sancho never reproduced his Borussia Dortmund form.

With just 12 goals in over 80 appearances, his output was a fraction of what was expected. By 2025, he was out on loan again, his reputation in tatters.

For a club already haunted by bad recruitment, Sancho is another expensive mistake.

2. Antony — £81.3m to Manchester United

If Sancho was disappointing, Antony has been outright disastrous. Signed by Erik ten Hag in 2022 for an eye-watering £81.3 million, Antony never came close to justifying the price tag.

Erratic on the ball, predictable in attack, and wasteful in possession, his stats tell the story: just 12 goals and five assists in 96 games. By 2025, United cut their losses and sent him to Real Betis.

Antony now stands as a symbol of the poor decision-making that has plagued Old Trafford in the post-Ferguson era.

1. Ali Dia — Free transfer to Southampton

No list of Premier League disasters is complete without Ali Dia. His story is so ridiculous that it almost feels like an urban legend. A man posing as George Weah phoned Southampton manager Graeme Souness, recommending Dia as a player with an international pedigree.

None of it was true. Dia was a semi-professional at best, but Souness gave him a trial and even put him into a Premier League match.

Within 53 minutes, it became obvious he didn’t belong, and he was hauled off. He never played for the club again. No money was wasted, but the embarrassment was priceless.

Honorable Mentions

Eliaquim Mangala
Alberto Aquilani
Owen Hargreaves
Yannick Bolasie
Ricky Alvarez
Bosko Balaban
Francis Jeffers
Adrian Mutu
Dani Osvaldo
Tomas Brolin
Winston Bogarde
Mario Balotelli
David Bentley
Saido Berahino