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Analysis
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Chelsea’s 10 biggest transfer sale mistakes
9 May 2026 12:01 CDT |
7 min read
Analysis
Chelsea have long been known as one of the most active clubs in the transfer market, with Roman Abramovich's takeover of the club in 2003 setting the scene for the Stamford Bridge side to become a powerhouse when it comes to wheeling and dealing for players.
Abramovich may have gone, but that spirit persists in BlueCo. It took Todd Boehly a matter of months to splash out more than €1 billion on players, though the end results have been distinctly mixed, with fans frustrated at what Chelsea have subsequently produced on the park.
While it's often been the Blues' big spending that has caught the headlines, the Stamford Bridge side have quietly worked well to establish themselves as a club that often works well when it comes to selling players - think the €115 million deal that sent Eden Hazard to Real Madrid.
But that's not to say they always get it right. Here are 10 examples of players the Blues let go too soon or too cheaply in deals that have left the club with a sense of regret.
Fikayo Tomori - €31.6m (to Milan, 2021)
Fikayo Tomori's form in Italy ensures he makes it onto this list.
A graduate of the Cobham academy, Tomori broke into the senior team under Frank Lampard, who had previously coached him at Derby.
He scored a wonder goal against Wolves before putting in some excellent performances in the Champions League. However, he was then frozen out by Lampard and featured just once in the Premier League during the 2020-21 campaign.
He joined AC Milan on loan in January 2021, and his talent shone through. The Italian club exercised their buy option, ensuring Tomori signed permanently. He helped them win their first Serie A title in 11 years in 2022.
Tomori would work his way into the England squad and amass over 200 appearances for one of Europe's biggest clubs. All the while, Chelsea struggled to find a settled central defensive partnership.
Thibaut Courtois - €35m (to Real Madrid, 2018)
Thibaut Courtois is included for what followed his departure - the signing of Kepa Arrizabalaga. With Courtois pushing for a move to Real Madrid, his wish was finally granted in 2018.
However, his departure in August left Chelsea scrambling for a replacement. In the end, they rushed their decision and paid a world-record fee for a goalkeeper on Kepa. Athletic Bilbao never sell cheap, due to their Basque rule, yet Chelsea didn't hesitate to splash out €80m in a record that still stands nearly a decade on.
The move for Kepa didn't work out, and the Blues were forced to sign Edouard Mendy in 2020 after the Spaniard's poor form. Robert Sanchez and Djordje Petrovic followed in 2023.
After a slow start, Courtois has proven himself as one of the world's very best goalkeepers. Ironically, Kepa joined Real Madrid on loan in 2023 after the Belgian suffered an ACL injury.
Mohamed Salah - €15m (to Roma, 2016)
After ripping apart the Chelsea defence for Basel in the Europa League, Mohamed Salah had done enough to convince the Blues to sign him for €16.5m in January 2014.
However, in a front line bristling with attacking talent, he was rarely handed a chance at Stamford Bridge. Salah was loaned to Fiorentina before Roma snapped him up.
After moving to Italy, Salah reached new heights. His electric style suited Serie A, and he moved back to England with Liverpool in 2017.
After a record-breaking first season, in which he scored 32 Premier League goals and 10 more in the Champions League, he carried that form to help Liverpool win the Champions League and the Premier League.
Salah, who has had a knack of scoring against Chelsea, has become one of Liverpool's greatest ever players, leaving the Blues thinking what might have been.
Romelu Lukaku - €35.4m (to Everton, 2014)
Sold for €35.4m then re-signed for €113m - that's the story of Romelu Lukaku at Chelsea.
Spells at Everton, Manchester United, and Inter Milan sandwiched his time at Stamford Bridge, and he scored everywhere he went.
The all-time top goal-scorer for the Belgium national team, Lukaku's total career transfer fees add up to over €200m, of which Chelsea contributed a huge amount when he returned in 2021.
The deal was a disaster. Injury hampered him and he would be sent on loan to Inter, again, and then Roma. He would eventually move to Napoli, where he won the Serie A title, yet it was his first move away from Chelsea that is the West London side's real cause for regret.
Kevin De Bruyne - €22m (to Wolfsburg, 2014)
Just like Salah and Lukaku, Kevin De Bruyne was a youngster never given a chance at Chelsea after being signed from abroad.
He found refuge in Germany after struggling at Stamford Bridge, and after a loan spell to Werder Bremen, Wolfsburg signed him. 18 months later, and they had turned an enormous profit on him.
De Bruyne joined Manchester City and the rest is history. He was widely considered the best player in the Premier League for much of his time at the Etihad Stadium - winning numerous league titles and the Champions League in 2023.
He also holds the record for the most assists in a single Premier League season, with 20 (joint with Thierry Henry).
Daniel Sturridge - €15m (to Liverpool, 2013)
Mostly deployed off the right wing for Chelsea, Daniel Sturridge joined Liverpool to form the SSS attacking trio at Anfield. Alongside Raheem Sterling and Luis Suarez, Sturridge thrived, bagging 22 league goals as Liverpool lost out to Man City in the title hunt in 2014.
Injury problems plagued his footballing career, but for that season, he was almost unstoppable.
Chelsea missed out.
Arjen Robben - €35m (to Real Madrid, 2007)
One of the most exciting players to watch on his day, Arjen Robben helped Chelsea to their first two Premier League titles before leaving for Spain.
His time at Real Madrid didn't exactly go to plan, but he subsequently found his feet and his home at Bayern Munich.
Eight Bundesliga titles followed, with Robben also scoring the winning goal in the 2013 Champions League final - redemption after missing a penalty during the previous year's final against Chelsea.
A right winger who could've helped Chelsea to even more success, but it wasn't to be.
Samuele Dalla Bona - €1.6m (to Milan, 2002)
A more niche choice here, but Samuele Dalla Bona could've been something special. After netting 18 goals for Chelsea's reserve side, from midfield, Dalla Bona made 32 appearances for the Blues' senior team during the 2000/01 season.
However, he turned down a contract extension in favour of returning to Italy. He joined AC Milan, but managed just four appearances for the club before eventually being sold in 2006.
Dalla Bona then bounced around Serie A, but never found a home. If he'd have stayed at Chelsea, both the player and the club could've benefitted.
Gianfranco Zola - Free (to Cagliari, 2003)
Aged 37 when he left Chelsea, Gianfranco Zola rejected a new contract at Stamford Bridge and went back to his homeland, to the disappointment of all associated with the Blues.
He'd managed 21 goal contributions in the league in his final season, and he had at least one more good year left in him.
Zola opted to go back to Italy, however, joining Cagliari in Serie B.
Tammy Abraham - €41m (to Roma, 2021)
Chelsea had a fine young forward in Tammy Abraham amongst their ranks but rarely played him, and he was sold off to Roma, where Jose Mourinho was eager to make the best out of him.
In his first season, he played a starring role, helping his new club win the UEFA Europa Conference League - their first continental title - and earned his place back in the England squad under Gareth Southgate.
Chelsea, meanwhile, struggled for goals as their forwards Timo Werner and Romelu Lukaku were misfiring, forcing them to dive back in the market in 2022 and sign an ageing Pierre-Emerick Aubameyang, who was a disaster.
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