Chelsea's 15 worst transfers in history — Ranked

Since Roman Abramovich took over Chelsea, they have been known for making big-name signings. Some have paid off, such as Didier Drogba, Eden Hazard, and Ashley Cole. However, there have been expensive mistakes, including Fernando Torres, Andriy Shevchenko, and Romelu Lukaku.

The Blues have signed many top players, but many have flopped at Stamford Bridge. This list is not ranking the players on their overall careers but on their transfer to Chelsea and how they fared at the club. This is based on the fee, their performances, whether they lived up to expectations or not, and whether any money was recouped. This list is subjective, and of course it is difficult to compare transfer fees in different eras.

15. Mateja Kežman

Mateja Kežman was prolific for PSV Eindhoven, scoring 129 goals in 176 games. This led to Chelsea paying £5.3 million for him back in 2004. He went on to score just seven goals in 41 games for the Blues. He was thought to be the next Ruud van Nistelrooy but never lived up to the hype. However, he did score what turned out to be the winner for Chelsea in the League Cup final against Liverpool. Also, the Blues broke even on transfer fees for him, as they sold him to Atlético Madrid for the same amount they paid for him.

14. Shaun Wright-Phillips

Shaun Wright-Phillips burst onto the scene at the moment Manchester City. Chelsea then signed him for £21 million in 2005, but he was inconsistent for the West London side. In 125 games for the Blues, he scored just 10 goals with 15 assists. The winger was then sold back to City for £8.5 million.

13. Chris Sutton

Chris Sutton was a Premier League champion with Blackburn Rovers when he signed for Chelsea. However, the £10 million the Blues paid in 1999 turned out to be a waste. He scored just three goals in 39 games for Chelsea before he rebuilt his reputation with Celtic. He was sold to the Scottish side for £6 million, so the Blues got back just over half of what they paid for him.

12. Tiemoué Bakayoko

Tiemoué Bakayoko had just won Ligue 1 with AS Monaco when Chelsea signed him in 2017 for £40 million. He was supposed to be the long-term replacement for Nemanja Matic, who had joined Manchester United. However, in total, he played just 43 games for the Blues. He was sent on multiple loans, where he spent time at Milan (twice), back at Monaco, and Napoli. He then joined Lorient permanently on a free transfer.

11. Khalid Boulahrouz

Khalid Boulahrouz was a highly rated player while at Hamburger SV. He joined Chelsea for £8.5 million in 2006. It was always going to be difficult for the centre-back to get game time ahead of John Terry and Ricardo Carvalho. Therefore, he played just 23 times for the Blues. He was loaned to Sevilla before making a permanent move to Stuttgart. The Blues managed to get back nearly half of what they signed him for, as they sold him for £4 million.

10. Juan Sebastián Verón

Juan Sebastián Verón had already been a flop at Manchester United when he joined Chelsea for £15 million in 2003. He was also poor with the Blues, playing just 14 games, scoring once and assisting once. Verón was sent on loan to Inter Milan and Estudiantes de La Plata. He then joined Estudiantes permanently on a free transfer. There is no doubt that Verón was a good player, as he earned 72 caps for Argentina. However, his transfer to Chelsea was bad.

9. Danny Drinkwater

After winning the Premier League with Leicester City, Danny Drinkwater was in high demand. He joined the Blues for £35 million in 2017. However, he made just 23 appearances for Chelsea, scoring once. Drinkwater was sent on multiple loans before his days as a professional footballer ended. He was loaned to Burnley, Aston Villa, Kasımpaşa and Reading. The end of his loan with the Royals coincided with his release from Chelsea in 2022. Drinkwater then retired a year later after not finding another club.

8. Álvaro Morata

Álvaro Morata already had Real Madrid and Juventus on his CV when he signed for Chelsea in 2017 for £60 million. The striker was inconsistent, scoring 24 goals with six assists in 72 games for the Blues. He went on loan to Atlético Madrid before joining the La Liga side permanently. Chelsea at least managed to recoup most of their transfer fee as they sold him for £50 million.

7. Adrian Mutu

Chelsea paid £15.8 million to Parma for Adrian Mutu in 2003, and he went on to have an eventful time in West London. He scored 10 goals with nine assists in 38 games for the Blues. However, he fell out with José Mourinho and tested positive for cocaine, which led to his contract being terminated. Chelsea then sued Mutu for £14.3m. Mutu would go on to be successful in Italy once again, representing Juventus, Fiorentina and Cesena.

6. Kepa Arrizabalaga

Kepa Arrizabalaga is best known for refusing to be substituted by Mauricio Sarri in the 2019 League Cup final. The Blues had paid £71.6 million to Athletic Bilbao for the goalkeeper the year prior. He did play 163 times for Chelsea, keeping 56 clean sheets. However, his form did not recover after the League Cup incident. He was sent on loan to Real Madrid and AFC Bournemouth before he joined Arsenal permanently. However, his time with the Gunners has been spent as David Raya's backup.

5. Mykhailo Mudryk

Mykhailo Mudryk has recently returned to first-team action with Chelsea following a doping ban. He was signed by the Blues from Shakhtar Donetsk for £62 million, which could rise to £89 million. The winger has scored just 10 goals with 11 assists in 73 games for the Blues so far. Despite being reintegrated into Chelsea's squad this pre-season. Transfers to Coventry City or Strasbourg appear to be on the cards.

4. Andriy Shevchenko

The recent documentary on Mourinho on Netflix has revealed that Andriy Shevchenko was signed by Abramovich despite the manager wanting Samuel Eto'o instead. Shevchenko cost the Blues £30.8 million from AC Milan. However, he scored just 22 goals with 13 assists in 77 matches for the West London side. He was sent back to Milan on loan before returning to his former club, Dynamo Kyiv, permanently.

3. Romelu Lukaku

Romelu Lukaku had already had a brief spell at Chelsea earlier in his career when the Blues paid £97.5 million to bring him back to the club from Inter Milan in 2021. He failed to adapt back to English football. In total across both his spells at Stamford Bridge, Lukaku scored just 15 goals with three assists in 59 games.

Lukaku publicly criticized Thomas Tuchel's tactics in an interview with Sky Italia. He was then dropped by Tuchel but was restored after the player had apologized. Lukaku also stated that he wanted to return to Inter in his talk with Sky Italia. He got his wish as he was sent on loan to Inter and then to AS Roma. Lukaku then made a permanent move to Serie A when he joined Napoli for £30 million.

The Belgian is now with Fenerbahce. A good striker, but his time in England, which also included playing for West Bromwich Albion, Everton and Manchester United, was mixed. With the amount spent on Lukaku overall by Chelsea, and given his poor return, it could be argued that his transfer was the club's worst ever.

2. Fernando Torres

Fernando Torres was a very highly rated player at Liverpool when Chelsea signed him for £50 million in 2011. There was much excitement when the Blues signed him from a Premier League rival. However, the pressure of the high transfer fee led to the player losing confidence.

Torres was also still competing for a starting spot with Didier Drogba at the time he joined the Blues. In 172 games for Chelsea, he scored 45 goals with 30 assists. Notably, he scored the goal that sealed the victory over Barcelona in the semi-finals of the Champions League in 2012.

The striker went on loan to AC Milan before joining them permanently on a free transfer. However, he was then sent straight on loan to his former club, Atlético Madrid. With such a high transfer fee, failing to live up to expectations before leaving for nothing, it could be argued that he is Chelsea's worst ever transfer.

1. Winston Bogarde

Chelsea's worst signing has to be Winston Bogarde, who surprisingly joined the club on a free transfer. However, the player who joined the Blues from Barcelona ended up costing a lot in wages, as he was on £40k a week.

He was at the Blues from 2000 until 2004 and played just 12 times. This meant that, in total, Chelsea paid him £8 million in total. The player was just happy to pick up the money despite not playing. This was before Abramovich had taken over the club, so it was a huge financial burden at the time. He had a good CV, having also represented AC Milan, Ajax and Sparta Rotterdam. However, after his time at Chelsea, no one was going to take a chance on him again.

Torres and Lukakau were both hefty price tags, but they at least had some return. They were also signed in the Abramovich era, when the club could afford to buy these players. Many young Chelsea fans may not have heard of Bogarde. However, he has got to be the club's worst ever transfer.

Chelsea's 15 worst transfers at a glance

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