- 19 hours ago
Chelsea's 10 worst transfers of all time
Cameron Smith
- Updated: 6 Mar 2025 10:05 CST
- 8 min read
Analysis
Chelsea have been one of the major forces in the transfer market during the 21st century, with the Blues spending billions on new signings under Roman Abramovich and Clearlake Capital.
Under Abramovich, Chelsea built a squad capable of rivalling Manchester United and other clubs in Europe, while they have now pivoted towards a more sustainable method of buying and selling young players.
However, a number of big-money arrivals simply haven't lived up to the hype over the past few years,
Below, FootballTransfers runs through the 10 worst Chelsea signings of the new millennium.
Romelu Lukaku - €113m (from Inter Milan, 2021)
Romelu Lukaku declared he had 'unfinished business' when he returned to Chelsea from Inter Milan in 2021 for a club-record fee of €113m.
However, the Belgian forward's second stint at Stamford Bridge was a disaster, compounded by an explosive interview just a few months into his return where he criticised manager Thomas Tuchel's tactics.
After scoring just eight goals in the league, Lukaku returned on loan to Inter for €8m. A year later he went on a second loan to Roma for €5m as Chelsea found it almost impossible to sell him permanently.
They did finally manage to sell him in the summer of 2024 at a massive loss to Napoli for €30m. He will go down as one of the worst signings in not just Chelsea's history, but across every club in world football.
Kepa Arrizabalaga - €80m (from Athletic Club, 2018)
Due to their policy of only fielding players from the Basque region, it’s extremely expensive to pry players away from Athletic Club, as Chelsea found out with Kepa Arrizabalaga.
They agreed to pay world-record fee for the Spaniard as a replacement for Real Madrid-bound Thibaut Courtois, but the deal has been a disaster.
Kepa was responsible for one of the worst goalkeeping seasons in Premier League history during the 2019-20 campaign and he was soon replaced by Edouard Mendy,
Kepa left on loan for Real Madrid in the summer of 2023 and he then joined Bournemouth on loan in 2024 having become surplus to requirements.
Tiemoue Bakayoko - €40m (from Monaco, 2017)
Part of the famous AS Monaco squad that won the Ligue 1 title in 2016-17, Tiemoue Bakayoko arrived at Chelsea with high expectations.
He was a powerful destroyer, and appeared the perfect replacement for the Man Utd-bound Nemanja Matic.
However, a red card during a humiliating defeat to Watford saw his career at Chelsea fall off a cliff and he was loaned out to AC Milan, Monaco, Napoli and then back to Milan again before joining Lorient on a permanent deal in 2023.
Mykhailo Mudryk - €70m (from Shakhtar Donetsk, 2023)
Mykhailo Mudryk was destined to join Arsenal in January 2023, but Chelsea hijacked the deal at the last minute after reaching an agreement to sign the Shakhtar Donetsk winger for an initial €70m.
The Ukrainian has time to justify Chelsea’s huge outlay, but he failed to score until his 24th appearance for the club and he was provisionally suspended from football in December 2024 after a positive doping test.
This transfer has been a complete failure so far, and Mudryk appears unlikely to turn his Chelsea career around.
Danny Drinkwater - €37.9m (from Leicester, 2017)
In one of the more bizarre moves from this list, Danny Drinkwater joined Chelsea for €37.9m in 2017 in an extremely strange transfer.
Of course, he played a vital role in Leicester’s Premier League title win, but N’Golo Kante was the star of the Foxes' midfield and although Drinkwater did the basics well, he wasn’t Chelsea quality, and so it proved.
Drinkwater amassed just 23 first-team appearances for Chelsea and after loan spells at Burnley, Aston Villa, Kasimpasa and Reading, he left Stamford Bridge in 2022 upon the expiration of his contract.
Alvaro Morata - €66m (from Real Madrid, 2017)
Alvaro Morata was never a consistent regular at Real Madrid, but the form he displayed on loan at Juventus, and during his fleeting appearances for Los Blancos, suggested that he was a talismanic figure with expert instincts in the box.
That prompted Chelsea to complete a €66m deal in 2017, even though Antonio Conte publicly stated he wanted Romelu Lukaku instead.
Morata scored 15 goals and assisted six in 30 starts in all competitions during his first season at Chelsea, but poor finishing in his second year, and just five Premier League goals in 2018-19, saw him loaned to Atletico Madrid for €18m, before they signed him for on a permanent deal for €35m.
He may have recouped most of his transfer fee, but Morata’s time at Chelsea was not a pleasant one.
Adrian Mutu - €22.7m (from Parma, 2003)
Adrian Mutu netted four goals in his first three games for Chelsea, and it looked as though Abramovich had found an absolute gem.
It wasn’t to be, however, as the striker only scored a further six goals and was soon banned from football for seven months for cocaine use.
The club then sacked Mutu before starting a legal battle against him. The case ended up at the Court of Arbitration for Sport, and in 2009 Mutu was ordered to pay damages to the club.
It was a mess of a transfer, and one that the club will want to forget.
Andriy Shevchenko - €43.9m (from AC Milan, 2006)
Andriy Shevchenko was a long-time target for Abramovich, but when he eventually landed him in 2006, the Ukraine international was 29 and past his peak.
He scored on his debut in the Community Shield against Liverpool, but failed to kick on, losing out to Drogba in the battle to become Chelsea's preferred centre forward.
After scoring 23 goals in 77 games for Chelsea, Shevchenko was loaned back to Milan two years later, before returning to Dynamo Kyiv on a free transfer in 2009.
Fernando Torres - €58.5m (from Liverpool, 2011)
Fernando Torres was a roaring success at Liverpool, with 69 Premier League goals in his three-and-a-half seasons at Anfield, but he never hit the same heights at Chelsea.
A warning sign should’ve come with his injury issues, and the fact that whilst he netted 18 league goals in just 1,717 minutes in 2009-10, Torres was on the decline in 2010-11.
Chelsea still forked out an English record fee at the time to acquire his services, and although he netted that famous goal at Camp Nou, he ultimately didn’t live up to expectations.
It took him nearly 1,000 minutes to net his first Chelsea goal and he left Chelsea to join AC Milan for just €1m in January 2015.
Juan Sebastian Veron - €21.8m (from Man Utd, 2003)
We end with a move away from strikers, and Juan Sebastian Veron is next on the list.
Having failed to fit in at Man Utd, whilst showing his obvious class, Veron simply failed to produce at Chelsea. He managed to play just 14 games in the league, scoring once and grabbing two assists.
He didn’t fit into the system, and after a loan spell at Inter Milan, he was sold to Estudiantes for a mere €2.2m in 2006.
