Chelsea Transfers: The 10 Worst Signings in Premier League Era

Chelsea have signed some remarkable footballers over the past three decades in the Premier League – but also some incredible flops. It stands to reason that when a Russian billionaire buys your club, he's going to want to spend money. Then, when an American tycoon takes over, he's going to love splashing the cash too.

Chelsea transfer spending reached £2bn on new players in the decade between 2013/14 and 2023/24.

The Blues haven't always got their transfer policy right and in recent years have hoarded young talent in an effort to overcome financial sustainability rules. They were also the first to offer eight-year contracts to players, in order to amortise their spending over more years.

There are some great accountants in west London but also some frivolous managers and scouts.

Below, we've picked the 10 worst Chelsea signings in Premier League history. Three of them were free transfers, while some were eye-wateringly expensive. All were flops.

Worst Chelsea Transfers Ever

1. Kepa Arrizabalaga – £71.6m
1. Fernando Torres – £50m
1. Steve Sidwell – Free
1. Alvaro Morata – £60m
1. Kalidou Koulibaly – £33m
1. Juan Sebastian Veron – £15m
1. Winston Bogarde – Free
1. Mark Bosnich – Free
1. Romelu Lukaku – £97.5m
1. Danny Drinkwater – £35m

10. Kepa Arrizabalaga – £71.6m

Chelsea had one of the world's best goalkeepers in 2018 but couldn't keep Thibaut Courtois away from Real Madrid. They responded to the Belgian's departure by breaking the world transfer record for a goalkeeper. Kepa Arrizabalaga cost the Blues £71.6m but he hasn't proved value for money.

He refused to be substituted in the 2019 EFL Cup Final, which Chelsea lost to Manchester City on penalties. He struggled to compete with veteran Willy Caballero for the first-choice goalkeeper spot the following season, and was then benched almost permanently when Edouard Mendy joined the club.

Kepa was moved on loan to Real Madrid for the 2023/24 season, where he barely played. He is arguably the victim of Chelsea going through five managers during his stint in London.

9. Fernando Torres – £50m

The reason Fernando Torres was such a flop at Chelsea was because he was so good for Liverpool. The Anfield icon quit Merseyside in search of trophies in 2011, and duly won the Champions League, Europa League and FA Cup. But his £50m price tag proved too heavy a weight to carry.

Torres never scored more than eight league goals in any of his four Premier League seasons at Stamford Bridge. He was shifted out on loan to Milan in 2014 but lasted just 10 games before moving on loan to his former club Atletico Madrid.

That was the end of his Chelsea career. As for Liverpool, they spent 70% of the Torres transfer fee on Andy Carroll. Neither fan base was happy with what they got.

8. Steve Sidwell – Free

Reading offered Steve Sidwell a £25,000-per-week, four-year deal in the summer of 2007 but the midfielder opted to join Chelsea on a free transfer instead. Newcastle United, Everton and Aston Villa had also been interested, yet Chelsea were going places.

Jose Mourinho thought he'd landed a bargain. What he'd actually signed was a free flop. Sidwell scored just once in 25 games for Chelsea that season. He started just 13 matches and didn't even feature after February. Aston Villa bought him the following summer, which at least earned Chelsea a trading profit.

7. Alvaro Morata – £60m

Alvaro Morata captained Spain to Euro 2024 glory, has won two La Liga titles, two Serie A championships, and the Champions League twice. He even won the FA Cup and Europa League while on Chelsea's books. Yet his stint in west London marks the low point of his remarkable career.

Morata joined Chelsea in the summer of 2017 for £60m. replacing fan favourite Diego Costa. He endured a miserable time despite winning trophies. He scored just 16 league goals across two seasons and faded away when Maurizio Sarri took over.

He moved to Atletico Madrid on loan in 2019 and moved to Spain permanently in the summer of 2020.

6. Kalidou Koulibaly – £33m

Kalidou Koulibaly had been rumoured with a move to the Premier League for years when, at the age of 31, he finally left Napoli for England. He joined Chelsea for £33m and immediately went into the heart of Thomas Tuchel's defence.

Graham Potter succeeded Tuchel within months of Koulibaly's arrival and the defender kept his place for a while, before crashing out of favour when Frank Lampard became manager again.

Within a year, the sought-after Ivorian had quit London for Saudi Arabia in a £20m move to Al-Hilal. He was not worth the media hype that for years had tipped him as a guaranteed hit for whichever Premier League team would sign him.

5. Juan Sebastian Veron – £15m

Juan Veron had a fairly average career at Manchester United. He won the Premier League under Sir Alex Ferguson in 2003 but his £28m price tag was always considered a little high. Ferguson sold Veron to Chelsea after that Premier League title victory, knowing the Argentine was past his best.

He was. Veron cost Chelsea £15m and he paid them back with seven Premier League appearances. He scored just one goal and spent much of the season injured. Jose Mourinho immediately sought to sell Veron when he took over at the Bridge the following summer. He played for Inter across two loan spells and won two Coppa Italias and the 2006 Serie A title.

As for Ferguson, he replaced Veron with Eric Djemba-Djemba, Kleberson and Alan Smith.

4. Winston Bogarde – Free

There are plenty of myths around Winston Bogarde's career at Chelsea. He has rubbished claims he used to fly from his home in Barcelona for training, and then fly out again. He insists he didn't go on strike or simply sit on the bench and rot.

What actually happened with Winston Bogarde is this. He joined Chelsea in the summer of 2000 under manager Gianluca Vialli, although the Italian didn't know the deal was happening. A week later Chelsea sacked Vialli and Claudio Ranieri came in. He wasn't interested in Bogarde.

The Dutchman says he and the club sought a loan move but no-one would pay his £40,000-a-week wages. Bogarde says he was even willing to take a 30% pay cut, but still there were no suitors. Chelsea started a cost-cutting exercise in 2002. Remember, this was before Roman Abramovich came on the scene. He retired in 2004 when his contract expired, having cost Chelsea more than £10m in wages.

3. Mark Bosnich – Free

Another free transfer that ended up as a flop. Mark Bosnich joined Chelsea from Manchester United in 2001 on a £40,000-a-week salary. Injuries kept him out of action for around six months and in November that year he played his last game for the Blues, against Everton.

Bosnich couldn't get back into the team after that and in September 2022 failed a drugs test. He was handed a nine-month ban and his career at Chelsea ended in ignominy.

2. Romelu Lukaku – £97.5m

Chelsea signed Romelu Lukaku for £10m in 2011 but did nothing with him. After a forgetful first season, he went on loan to West Brom and then Everton, and eventually secured a permanent move to Goodison Park. That would be the last Chelsea saw of Lukaku until 2021, when they suddenly got a whiff the then-Inter striker was for sale.

Inter, who had signed Lukaku from Manchester United, needed cash fast. Lukaku wanted to play in the Premier League again and Chelsea were happy to oblige. They struck a £97.5m deal that Inter naturally accepted. Lukaku re-joined Chelsea but struggled under boss Thomas Tuchel and held an interview with Italian media hinting that he wanted to return to Serie A.

Chelsea were furious and Lukaku's season was effectively over. He returned to Inter on loan the following summer for a loan fee worth less than 10% what Chelsea paid for him. He then went on loan to Roma under similar circumstances for the 2023/24 season and, as of summer 2024, is still a Chelsea player.

1. Danny Drinkwater – £35m

The reason Danny Drinkwater is the biggest flop in Chelsea transfer history is because the deal should never have happened. In 2017 Drinkwater, a Premier League champion with Leicester the previous season, was looking for a new club. Leicester had sacked Claudio Ranieri, N'Golo Kante was gone, and there were rumours about Riyad Mahrez and Jamie Vardy seeking moves.

Chelsea, meanwhile, were sweating over the newly-introduced "Home Grown Player" rule that meant they needed English talent fast. Drinkwater was available and Chelsea were after midfielders. He fit the bill and duly signed a five-year contract.

However, managerial changes at Stamford Bridge again affected one of their new recruits. Maurizio Sarri wasn't interested in Drinkwater and two years after signing he was sent on loan to Burnley for six months. Then he moved to Aston Villa, and then Kasımpaşa in Turkey. He spent one final season on loan at Reading before retiring in 2023.