Ranking the 16 worst Premier League signings of all time

Highlights

• European soccer clubs have two transfer windows each season, allowing them to sign players. The English Premier League has a knack for spending exorbitant amounts of money on players who end up being disappointing.
• Some notable examples of bad signings in the Premier League include Nicolas Pepe, Angel Di Maria, Kepa Arrizabalaga, Bebe and Romelu Lukaku.
• These players either failed to meet expectations, performed poorly on the pitch, didn’t last long with the club, or were overpriced.

In European soccer, 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. In the 2023 summer transfer window, England’s first division of soccer spent a staggering £2.36 billion ($2.96 billion) on player acquisitions in just over two months, according to Squawka.

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 featured in,
• Money spent on the player,
• How much return for 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 didn’t live up to expectations. However, they weren’t quite as bad as this group though.

16 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.

15 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 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.

14 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. 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 had suffered serious injuries leading up to his move to Chelsea, and it’s become even worse since joining them. The 22-year-old signed for the club at the end of the 2022 summer transfer window, and he’s only played in 17 league games since.

13 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.

12 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.

Rodwell will forever be remembered in that part of the world for the negative effect that he had on the club, and it was immortalised in the Netflix series ‘Sunderland ‘Til I Die’.

11 Angel Di Maria

£67.5m to Manchester United

The Argentinian winger has had a very successful career in the sport, 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.

10 Kepa Arrizabalaga

£71.8m to Chelsea

Chelsea broke the world record for the amount paid to sign a goalkeeper when they bought Kepa, in 2018. The 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. 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.

9 Andriy Shevchenko

£39.5m to Chelsea

The flight from Milan to London seemed to drain the Ukranian 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 29-year-old was set to take Didier Drogba’s place in the team; that didn’t happen. Drogba got back in rhythm and 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.

8 Antony

£81.3m to Manchester United

Erik ten Hag has made a habit of bringing players to Manchester United that he has previously worked with. Lisandro Martinez is an example of a prior relationship working successfully at Old Trafford, but Antony has been the complete opposite. To fork out over £80 million on an attacking player that had only scored eight league goals for Ajax in the previous campaign was an obscene decision.

Manchester United have become famed for their poor record in the transfer window in the past decade, and the Brazilian is up there with the worst deals in the club’s history. The Sun have reported that the Red Devils are ready to listen to offers for Antony at the end of the 2023/24 season, with the 23-year-old failing to live up to expectation. His record of nine goals and four assists from 70 appearances in all competitions at the time of writing is bordering on abysmal.

7 Jean-Kevin Augustin

£15.5m to Leeds United

The Frenchman’s move to the Whites sounds pretty innocuous on the surface. He joined on loan from RB Leipzig at the end of the 2020 January transfer window. Of course, this was not long before the Covid-19 pandemic hit. Included in the deal was an obligation to buy Augustin at the end of the temporary move.

He only made three substitute appearances for a total of 48 minutes. Leeds argued that the obligation should be voided because of the pandemic causing a delay to the end of the season, but they were forced to pay the eight-figure fee to the German club for just over one half of a game’s worth of playing time, according to the Daily Mail.

6 Bebe

£7.9m to Manchester United

Sir Alex Ferguson is considered to be one of, if not, the greatest managers in the history of English soccer. His 13 Premier League titles speak for themselves, but this was his worst transfer decision during his time at Old Trafford. The Portuguese player, who had never played at a higher level than the third tier of his country’s soccer pyramid, was recommended to Ferguson by a former assistant who effectively broke his own rules in the process.

Bebe played all of 75 league minutes for the club before everyone finally realised that he was no good. Man United were so successful under the Scottish manager that this move is looked back on as a bit of a joke, rather than a detriment to the club.

5 Alexis Sanchez

£35m + Henrikh Mkhitaryan to Manchester United

The Red Devils probably thought that they’d embarrassed Arsenal by getting this deal over the line, but the only ones they embarrassed were themselves. Although they didn’t have to pay the Gunners to acquire their best player, they sure did pay the Chilean a lot of money.

Reports from The Guardian suggest that United paid Sanchez £391,000 per week, a £1.1m annual signing bonus, and £75,000 for every appearance he made. So, if you do the math, that works out at £3.3m just for playing for the club, let alone the weekly wage packet or the huge signing bonus.

4 Danny Drinkwater

£34.1m to Chelsea

At the time of the move, Drinkwater was on the edge of a spot in the England squad, having not long won the Premier League with Leicester. The 33-year-old retired from the sport in October 2023, and this move started his downfall.

He claimed that the manager Maurizio Sarri once tried to force him out in the last hour of a transfer window, only for the midfielder to refuse a move. He said on the High Performance podcast that he was out partying a lot, during his Chelsea days, to try and cover for everything else that was going on in his professional life.

3 Romelu Lukaku

£97.5m to Chelsea

Lukaku rejoined Chelsea in 2021 for a club-record fee. The club had just won the Champions League, and the hope was that he would be able to spur Chelsea on to a Premier League title win in the 2021/22 season. His first few games were very promising, and the club looked like worthy challengers to Manchester City’s throne.

But a lack of time with the team in pre-season led to struggles with fitness and rapport with teammates, according to The Athletic. They got eight league goals for that money. The word disappointment will forever follow the Belgian striker. Lukaku has spent the majority of his time since his return to Chelsea out on loan.

2 Ricky Alvarez

£9.5m to Sunderland

This is one that maybe goes under the radar a bit, but it sure was a facepalm moment in the offices of Sunderland AFC. Alvarez joined the club on loan from Inter Milan, in 2014, and the Black Cats had agreed to sign him permanently if they were to avoid relegation.

They did survive and, therefore, were obligated to pay up. However, they refused to, claiming that the pre-existing issues in his left knee, and a new one in his right, should void the payment. The Argentinian midfielder ended up joining Sampdoria on a free, but Sunderland were still ordered to pay the £9.5m fee, so they paid all that money for literally nothing. That payment, plus all the costs of fighting it, took Sunderland’s total bill for Alvarez to close to £20m, as per the Daily Mail.

1 Ali Dia

Free transfer to Southampton

This is just a mental story, but here goes. A man rang Southampton claiming to be World Player of the Year George Weah; that alone is bizarre, but it gets worse. The person posing as Weah recommended that Dia be signed by the club. The caller said that he’d played with Weah for PSG, scored twice for Senegal the week prior, and had played in the German second division.

None of this was true. The 31-year-old was a college student who had played semi-professional football at best. Manager Graeme Souness fell for it, brought him in for a trial, signed him, put him on the bench, and brought him on in a Premier League game. After 53 minutes, all had become clear, and he was taken off. A truly bizarre, and yet wonderful, story.

All statistics and transfer fees in the tables are courtesy of Transfermarkt. Correct as of February 27, 2024.