Following Roman Abramovich’s takeover in 2003, Chelsea dominated the English football transfer market.

The Blues initially invested enormous sums of money to assemble a team that could compete with Manchester United and other European clubs.

Then, once their dominance was undeniable, Chelsea shifted to a more long-term strategy for acquiring and offloading young players.

As a result, a number of high-priced players came and went from the London club, and occasionally they weren’t having very good times.

Todd Boehly spent more over €1 billion on new players in his first year after purchasing Chelsea in 2022. There are already a lot of costly failures that are expected to be on this list in the years to come.

Here at FootballTransfers, we take a look at the 10 worst Chelsea signings of the new millennium.

Romelu Lukaku – £99.5m from Inter Milan

When Romelu Lukaku returned to Chelsea from Inter Milan in 2021 for a nearly £100 million club record transfer fee, he claimed he had “unfinished business.”

The Belgian forward’s second time at Stamford Bridge, however, was a complete failure, which was made worse by a contentious interview he gave just a few months after his comeback in which he criticized manager Thomas Tuchel’s tactics.

Lukaku returned to Inter on loan for €8 million after only registering eight league goals. He went on a second loan to Roma for €5 million a year later when Chelsea was unable to sell him on a long-term basis.

He will be remembered as one of the worst signings ever, not just in the history of the club.

Kepa Arrizabalaga – £72m from Athletic Bilbao

Athletic Bilbao’s strategy of only using players from the Basque Country makes it very expensive to lure players away from the club, as Chelsea discovered with Kepa.

The team needed a successor for Thibaut Courtois, who was headed to Real Madrid, thus a world-record fee for a goalkeeper was agreed upon. However, things haven’t worked out as expected.

Kepa performed admirably under Maurizio Sarri; he wasn’t terrible and had promise, but he was by no means a world-class player. However, the 2019–20 season was a different scenario.

He made just 1.7 saves per 90, the fewest of any goalkeeper with more than one appearance in the league, and he had the lowest save percentage of all the goalies in the league, allowing 47 Premier League goals.

He was then replaced by Edouard Mendy as first choice as Chelsea gave up on the Spaniard.

Kepa left on loan for Real Madrid in the summer of 2023 having become surplus to requirements.

Tiemoue Bakayoko – £40m from Monaco

Part of that famous AS Monaco squad that won the Ligue 1 title in 2016/17, Tiemoue Bakayoko arrived in London with high expectations.

He was a powerful destroyer, and appeared the perfect replacement for the Man Utd-bound Nemanja Matic.

He started well, with a performance against Tottenham particularly strong, but he went off the boil, and a 30-minute red card in a humiliating defeat to Watford saw his career at Chelsea fall off a cliff.

He did make 24 Premier League starts in 17/18, but was clear that he didn’t fit Sarri’s system, and he was shoved to the side to accommodate Jorginho.

He was then loaned out to AC Milan, back to Monaco, then to Napoli and then back to Milan again. He finally left Chelsea permanently in 2023 on a free transfer to Ligue 1 side Lorient.

Michy Batshuayi – £33m from Marseille

Michy Batshuayi was seen as Chelsea’s next clinical number nine after impressing for Marseille in Ligue 1, but he turned out to be yet another failing forward for Chelsea.

Just as with many of Chelsea’s poor striker signings, a few of which will be mentioned later, he failed to produce on the Premier League stage, and while he scored the title-winning goal against West Brom in 2016/17, Batshuayi did not hit those heights again.

He spent the 2020/21 season on loan at Crystal Palace and then was sent out to Besiktas in 2021/22. He was finally sold to Fenerbahce in 2022 having scored only eight Premier League goals for Chelsea.

Danny Drinkwater – £35m from Leicester

One of the strangest choices on this list involved signing Danny Drinkwater in 2017, when he wasn’t actually that good.

Of course, Drinkwater was essential to Leicester’s championship victory, but N’Golo Kante handled the majority of the defensive job, leaving Drinkwater with nothing else to do. He was competent in the fundamentals, but it was clear that he wasn’t Chelsea caliber.

Drinkwater never made it onto the senior team, making just 23 overall appearances and one this season in the Football League trophy.

He spent time on loan at both Burnley and Aston Villa, however he was unable to play more than 500 minutes in total for both. Before taking out another loan at Reading, he next moved on loan to Kasimpasa. When his sentence expired in 2022, he

Alvaro Morata – £58m from Real Madrid

Alvaro Morata was never a dependable starter for Real Madrid, but his performance while on loan at Juventus and in his few outings for Los Blancos revealed that he was a talismanic player with keen boxing instincts.

Even though Antonio Conte publicly declared he wanted Romelu Lukaku, that pressed Abramovich’s hand, and Morata was signed. On his Premier League debut against Burnley, the club-record signing (at the time) nearly inspired a comeback by scoring once, getting an assist, and scoring a goal that was disallowed.

He scored 15 goals and assisted six in 30 starts in all competitions in his first season, but poor finishing in his second year, and just five Premier League goals in 2018/19, saw him loaned to Atletico Madrid for £16m, before they signed him for just over £30m permanently.

He may have recouped most of his transfer fee, but Morata’s time at Chelsea was not a pleasant one.

Adrian Mutu – £15.2m from Parma

The alternative to Shevchenko in 2004, 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, the striker only scored a further six goals and was then 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.

After appealing this, it was ruled in 2018 that Mutu owed Chelsea £15.2m in compensation.

It was a mess of a transfer, and one that the club will want to forget.

Andriy Shevchenko – £30.8m from AC Milan

Yet another ‘flop’ in the number nine position for Chelsea. Andriy Shevchenko was a long-time target for Abramovich and when he eventually landed him in 2006, the Ukranian 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 for the first choice slot up front, and altogether proving a waste of money.

With 23 goals in 77 games, Shevchenko still managed to net on a fairly regular basis, but it wasn’t what was expected of him, and ultimately, Drogba was preferred.

He was loaned back to Milan two years later, before leaving permanently to Dynamo Kyiv for free in 2009; the move to Chelsea didn’t work out.

Fernando Torres – £50m from Liverpool

Fernando Torres was a roaring success at Liverpool, with 69 Premier League goals in his three-and-a-half seasons there, 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 the Camp Nou, he ultimately didn’t live up to expectations.

It took him nearly 1,000 minutes to net his first Chelsea goal, and whilst 45 goals and 35 assists in 175 appearances isn’t awful (a goal contribution roughly every 2.2 games), he simply wasn’t as good as the club had hoped he would be.

Juan Sebastian Veron – £15m from Manchester United

Juan Sebastian Veron is the next striker on the list as we move away from them; the Argentine certainly didn’t live up to his name or his cost.

Veron struggled to perform at Chelsea after failing to blend in at Manchester United despite displaying his evident class. He was only able to participate in 14 games during his time in the league, recording one goal and two assists.

He didn’t fit into the system, and in 2006, after spending time on loan at Inter Milan, he was moved to Estudiantes for under £2 million. At Stamford Bridge, he never showed his full brilliance.

Mateja Kezman is often spoken as a Chelsea flop, but as he only cost £5m, he hasn’t been included in this list, although he, Juan Cuadrado and Davide Zappacosta are special mentions.