In European football, there are two transfer windows every season. These windows are the only time that clubs are allowed to sign contracted players – free agents can be signed at any time of the season. Players can be bought permanently from another club or brought in temporarily on loan.

Due to the ludicrous amounts of money in sports nowadays, these windows give soccer clubs a chance to recklessly spend their millions. Arguably, no league has proven themselves to be as good at spending money on players that turn out to be pretty much useless as the English Premier League.

The criteria for a bad signing consists of four main factors: price, expectation, success on the pitch, and longevity with the club. Usually, one or two of these factors can justify the transfer if the others are bad, but there’s not one case on this list where you can look at the move and go ‘Actually, that wasn’t that bad.’

Ranking factors

• Games that the player managed to feature in.
• The total money spent on the player – transfer fee/wages.
• How much return on investment the club received.

Some honourable mentions are players like Fernando Torres and Mario Balotelli. They have both had more than respectable careers, but their big-money moves to Chelsea and Liverpool respectively didn’t live up to expectations. However, they weren’t quite as bad as this group though.

20

Eric Djemba-Djemba

£4.1m to Manchester United

The Cameroonian is a regular custodian of these lists, but, even considering the player that he turned out to be, his price tag wasn’t a huge hit for the Red Devils. He was 21 when he signed for the club, and he was potentially being lined up to replace club legend, and captain, Roy Keane.

That never came to be, and his former teammate, Rio Ferdinand, succinctly summed up the midfielder’s time with the club when he was asked about Djemba’s time at United. His response, on the Filthy Fellas podcast, was: “He’s a nice guy, man.” A rather dismissive way to talk about a former teammate, as a player.

19

Davy Klaassen

£23.6m to Everton

The Dutch midfielder was the epitome of the Toffees’ bad spending over the last decade. He joined the club from Ajax in the summer of 2017. The Dutch side is renowned for the ability to produce good technical footballers, but Davy Klaassen didn’t prove to be one of them.

In total, he started just three matches in the Premier League for Everton and came off the bench in four other league games. He left the club the following summer to join German club Werder Bremen. This move, plus going back to Ajax and joining Inter Milan in the summer of 2023, showed there was a good player there; it just didn’t work at Everton.

18

Wesley Fofana

£75m to Chelsea

You can imagine just how loaded Chelsea have been throughout most of the Premier League era with how many times they’ve appeared so far, and there’s more to come. Wesley Fofana, at one time, looked like one of the best young defenders that the Premier League had to offer. The only concern was his injury record.

Fofana, one of the most expensive centre-backs in football history, had suffered serious injuries leading up to his move to Chelsea, and it’s become even worse since joining them. The 24-year-old signed for the club at the end of the 2022 summer transfer window, and he’s only played in 54 league games since.

17

Jack Grealish

£100m to Manchester City

After years of strutting his stuff for Aston Villa – and with everyone eventually tiring of the endlessly repeated statistic about him being the most-fouled player in the Premier League season after season – Jack Grealish finally secured a £100 million move to Manchester City in 2021.

It felt deserved, and he quickly justified the hype by helping the Cityzens to an unprecedented treble in just his second season. But the two campaigns that followed were flat, and his swagger all but disappeared. Across those final two league seasons at the Etihad, he managed only four goals – a meagre return for a nine-figure signing who was expected to deliver consistent impact. His days at Man City look numbered after he spent the 2025/26 season on loan at Everton.

16

Nicolas Pepe

£72m to Arsenal

The Ivory Coast international certainly came with great expectation, but he struggled to live up to the club’s record fee at the time. That record was broken in the summer transfer window of 2023 when they signed midfielder Declan Rice from fellow Premier League team West Ham United.

By no means was Pepe an awful player for the Gunners; he scored 16 league goals over his three Premier League seasons with the club. But, if a club is going to shell out money like that, they rightly expect a team-altering return on their investment, and Arsenal didn’t get that.

15

Jack Rodwell

£11.3m to Sunderland

The former Manchester City midfielder was a personification of Sunderland’s problems during his time with the club. Sunderland were relegated to the second tier of English soccer (the Championship) in 2017. The 17/18 season saw the club be relegated again, in which time he played two games whilst collecting a reported £70,000 per week, as per ESPN.

Even when they went down to the third tier, he was still set to make £43,000 a week before they mutually agreed to cancel his contract. Jack Rodwell will forever be remembered in that part of the world for the negative effect that he had on the club, and he – also regarded as one of the biggest flops in Premier League history – was immortalised in the Netflix series ‘Sunderland ‘Til I Die’.

14

Angel Di Maria

£67.5m to Manchester United

Angel di Maria has enjoyed a very successful career in the sport, with plenty of silverware to attest to his brilliance, but this is not a period he’ll want to remember. A move to England from Real Madrid looked to be yet another big step in his career. The opening month was promising. He won the club’s Player of the Month award, but he never rekindled that form after picking up an injury.

The winger later admitted, to the Spanish newspaper Marca, that he never even wanted to join the club, and an attempted robbery of his home in February 2015 made his desire to stay at the club even less. He was bought by Paris Saint-Germain a year after joining.

13

Tanguy Ndombele

£63m to Tottenham

Signed in 2019 for a then-club-record fee, Ndombele showed glimpses of his talent but never found consistency. His work rate and fitness were repeatedly criticised by managers, and he was loaned out multiple times. Despite the massive outlay, Spurs failed to get the best out of him, making Ndombele one of their worst-ever signings.

Ndombele’s failings seemed to be caused all by himself, too. He had all the ability in the world, but his attitude was what separated him from becoming world-class. He was Tottenham’s highest-earner alongside Harry Kane at one point. But he was eventually released and signed for Nice in Ligue 1, meaning the north London club didn’t even manage to recoup any wasted fees spent on him,

12

Kepa Arrizabalaga

£71.8m to Chelsea

Chelsea broke the world record for the amount paid to sign a goalkeeper when they bought Kepa Arrizabalaga, in 2018. The then-23-year-old immediately had the weight of the world on his shoulders; expected to have the maturity to help lead the team to great things in years to come. It didn’t work.

What people might remember him most famously for is him refusing to be substituted in the Carabao Cup final (see above). Manager Maurizio Sarri was barking at him from the sidelines to try and get him off, to bring on Willy Caballero. The Spaniard refused, and his team went on to lose the final. He joined Arsenal in 2025 after they met the £5 million release clause in his contract.

11

Andriy Shevchenko

£39.5m to Chelsea

The flight from Milan to London seemed to drain the Ukrainian forward of all the brilliance that he’d shown previously in his career. The money they paid for him was a British transfer record at the time, and the striker was set to take Didier Drogba’s place in the team; that didn’t happen.

The aforementioned Drogba got back in rhythm and Andriy Shevchenko was never able to dislodge him. He scored just nine goals for the club. His career, prior to the move to London, was a flourishing one, which made it all the more disappointing that he wasn’t able to recreate those good times with Chelsea.