Chelsea’s 10 biggest transfer sale mistakes

Cameron Smith

• Updated: 15 Oct 2023 08:49 CDT
• 5 min read

With Roman Abramovich's takeover of the club in 2003, Chelsea immediately established themselves as a powerhouse of English and European football.

Abrahmovich's influx of money allowed Chelsea to buy a seemingly infinite amount of talent, and it enabled them to reach the heights of Champions League glory. Abramovich's successor Todd Boehly has already spent over €1 billion on players as he continues the big spending.

Chelsea have also often done well when it comes to selling players. However, some of their sales didn't go as planned. While Chelsea have often been able to extract value for money, think selling Alvaro Morata and Eden Hazard for a combined £143 million, sometimes they've got it wrong, and there are some notable examples.

Who are Chelsea's 10 biggest transfer sale mistakes?

Fikayo Tomori - AC Milan, 2021 (£25m)

Having only signed on a permanent basis in the summer of 2021, this may be too early to call, but 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 coached him at Derby previously.

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 then joined AC Milan on loan in January, and his talent shone through. The Italian club exercised their buy option, ensuring Tomori signed permanently. He helped them win a first Serie A title in 11 years in 2022.

Tomori has worked his way back into the England squad, and Chelsea will already regret letting him go.

Thibaut Courtois - Real Madrid, 2018 (£35m)

Thibaut Courtois is more so 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 spent a world record fee for a goalkeeper on Kepa. Athletic Bilbao never sell cheap, due to their Basque rule, yet Chelsea didn't hesitate.

The move for Kepa hasn't worked out, and the Blues were forced to sign another goalkeeper in 2020 after the Spaniard's poor form and then another in 2023.

After a slow start, Courtois proved himself as maybe the best goalkeeper in the world. When he got badly injured in 2023, Kepa ironically moved to Madrid on loan as cover.

Mohamed Salah - Roma, 2016 (£12.8m)

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 £14.9m (€17.5m) n January 2014.

However, in a front line consisting of plenty of talent, he never had much of a look in. Salah was loaned to Fiorentina before Roma snapped him up.

Since moving to Rome, Salah has 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 in the Champions League, he carried that form to help Liverpool win the Champions League and the Premier League in consecutive seasons.

He also loves scoring against Chelsea.

Romelu Lukaku - Everton, 2014 (£28m)

Sold for £28m, re-signed for £97.5m - the story of Romelu Lukaku at Chelsea.

Spells at Everton, Manchester United, and Inter Milan are in the middle of his time at Stamford Bridge, and he scored goals everywhere he went.

The all-time top goal-scorer for the Belgium national team, Lukaku's total career transfer fees add up to over £190m, but he's finally back at Chelsea now.

He helped Inter win Serie A in the 2020/21 season, and after searching for a new central striker, Chelsea landed on re-signing Lukaku for €115m. He proved to be a disaster in his first season back and has since been sent out on successive loans to Inter, again, and then Roma.

Kevin de Bruyne - Wolfsburg, 2014 (£18m)

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 a £36m profit on him.

De Bruyne joined Manchester City and the rest is history. He was widely considered as the best player in the Premier League for much of his time at City - 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 - Liverpool, 2013 (£12m)

Mostly deployed off the right wing for Chelsea, Daniel Sturridge joined Liverpool and not long after, he was part of the SSS attacking trio at Anfield. Alongside Raheem Sterling and Luis Suarez, Sturridge thrived, and he bagged 22 league goals as Liverpool lost out to Man City in the title hunt.

Injury problems have plagued his footballing career, but for that season, he was almost unstoppable.

Chelsea missed out.

Arjen Robben - Real Madrid, 2007 (£24m)

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 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 - Milan, 2002 (£1m)

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 side 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 - Cagliari, 2003 (Free)

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 the club hierarchy.

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 - Roma, 2021 (£36m)

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. He struggled more in his second campaign.

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 signing an ageing Pierre-Emerick Aubameyang, who was a disaster.