10 Players Chelsea Regretted Selling Too Early

Players Chelsea Regretted Selling: Chelsea has been in the headlines lately for the fact that they have spent over a billion pounds in a year. This is something that is unprecedented in the football world and what makes it worse is the fact that they’re getting even worse after this. Boehly’s regime has not gotten off to a great start and it doesn’t seem like it will reach the heights of the Abramovich era anytime soon.

Players Chelsea Regretted Selling

Despite all the success of their former Russian owner, the Blues could have won even more if they had taken a chance on this list of players. They went on to become superstars for other teams but were all at the Bridge before then.

1. Kevin De Bruyne

First, we have the player many people dub the greatest midfielder in Premier League history, Kevin De Bruyne. He is an offensive juggernaut and ever since signing for the sky blues has been a force to be reckoned with. At Chelsea, he struggled for minutes under former manager Jose Mourinho and was subsequently sold to Wolfsburg for a mere £16.7 million. Big mistake!

The following season he went on to win the German Footballer of the Year award for his remarkable performances in the 2014/15 season. This earned him a well-deserved move to the Etihad in 2015, where the whole world has been put on notice because of how good he is. He also recently made history with City, being part of their first Champions League title. He will always be remembered as a player Chelsea sold too soon.

2. Mo Salah

From one Premier League legend to another, Mo Salah is up next. He arrived at Chelsea in 2013, joining from FC Basel mainly due to the terror he had caused the Blues in a previous Champions League campaign. Upon failing to break into the first team, he was loaned out to Fiorentina the following year, scoring 15 goals in the process before being permanently sold to Roma in 2015.

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Players Chelsea Regretted Selling

His stellar displays in Serie A would go on to catch the attention of manager Jürgen Klopp who brought him to Anfield. He has gone on to win the Premier League, Champions League, and a myriad of individual awards such as the PFA Player of the Season and golden boot. He is now considered one of the greatest players the league has ever seen, something Chelsea fans can’t be too happy about.

3. Arjen Robben 

They didn’t just contribute to Premier League legends as Arjen Robben can confirm. One of the most exciting players to watch on his day, he helped Chelsea to their first two Premier League titles before leaving for Spain.

Players Chelsea Regretted Selling

His time at Real Madrid didn’t exactly go to plan, but he found his feet and his home at Bayern Munich soon after. 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. The Blues could have surely used him to bolster their attack in the past.

4. Jamal Musiala

Speaking of the Bundesliga, next up we have someone who will be hoping to leave a similar mark to Robben- Jamal Musiala. Since breaking into Bayern’s first team, he has emerged as one of the brightest talents in football. With an already stacked trophy cabinet including four Bundesliga titles, a Champions League and a Golden boy nomination, Chelsea missed out by letting him leave for next to nothing back in 2019.

Given that he was only 16 at the time and his value is now almost eighty million euros, you’d have to say Chelsea messed up big time on this one.

5. Declan Rice 

Another midfielder Chelsea let walk away for nothing is currently tearing it up at rivals Arsenal. Declan Rice was part of the Blues academy until the age of 14 when he left. Even though they didn’t actually sell him, they still let him go for free early on in his career when he was still developing, a decision that hasn’t aged well. He has turned into a key player for both club and country and is heralded as one of the best midfielders in the world.

Considering the Blues have spent an initial €299m on Enzo Fernandez, Moises Caicedo and Romeo Lavia since the start of 2023, letting Rice leave for free is a decision that will tick off plenty of Chelsea fans. Maybe they should have let him stay instead of Mount with how things have turned out.

6. Eddie Nketiah

The gifts to Arsenal don’t stop at just Rice as Chelsea also gave them their young striker Eddie Nketiah. He and Rice were even in the exact same youth team together. Nketiah was cast aside by the Blues in 2015 after seven years at the club’s youth academy after which he joined Arsenal. Despite not nailing a starting spot with the Gunners just yet, his ability is clear to see, and given how much Chelsea currently struggles in front of goal, his presence would surely be welcome.

7. Michael Olise

Chelsea tried to rectify a mistake they made in the summer by trying to sign Michael Olise from Crystal Palace. The Eagles would go ahead to threaten legal action and tie the Englishman to a long-term deal to dissuade the Blues and any other potential suitors. Crazy to think this whole scenario could have been prevented if Chelsea had kept hold of Olise in 2016. The London-born winger had spent seven years in the Blues academy before they decided he wasn’t good enough to keep at Cobham.

A short stint at Man City followed before he joined Reading in 2017. Olise then rose to prominence with the Championship team and earned a move to the Premier League in 2021. His breakout season was to come in 22/23 as he provided 11 league assists, the fourth highest tally in the Premier League. A shame Chelsea let him go.

8. Tino Livramento

We aren’t done with Premier League clubs that Chelsea has helped as up next we have Tino Livramento of Newcastle. Chelsea’s 2021 Academy Player of the Year shone at right wing-back during his time at Cobham but ultimately saw his first-team path blocked by fellow academy boy Reece James. Southampton saw an opportunity to sign the youngster in 2021 and lodged a bid of around €6 million, which was soon accepted by Chelsea.

He excelled in his debut season with the Saints but missed the next with an ACL injury. Newcastle had already seen all they needed to and decided to sign him in 2023. Under Eddie Howe, he has now begun to play as a left back which he is excelling at making him a true jack of all trades as he can also be a winger when needed. He has truly become a player Chelsea could currently have made great use of given injuries to key players.

9. Nathan Ake

Another defender is up next but he currently wears a different shade of blue from Chelsea’s- Nathan Ake. The Dutchman has slowly but surely become one of Guardiola’s most trusted players given his ability to play almost anywhere along the back line. Something fans may not know is that he spent six years at Chelsea after joining from Feyenoord aged 16, but that time included three loan spells, to Reading, Watford, and Bournemouth respectively.

He was later sold to Bournemouth for 20 million euros where he shone leading to Man City’s eventual interest. Given Chelsea’s issues with injuries in their defense, Ake would surely have been a great option to have.

10. Fikayo Tomori

We finish off the list with a player many Chelsea fans are familiar with, Fikayo Tomori. He was the first high-profile name to leave the Blues setup and move elsewhere when he joined AC Milan in early 2021. The Englishman had been a key figure in Frank Lampard’s first season in charge, but soon saw his place taken by Thiago Silva and was unable to work his way back into the starting 11.

Tomori has since proven himself to be an excellent center-back in Serie A, emerging as one of the division’s very best in his position. Since his exit, Chelsea have spent over €200m on new center-backs, at least some of which would’ve been avoided had they kept faith in Tomori.

Do you know any other players Chelsea let go of too soon?

Let us know in the comments.

Keep reading: Chelsea Secure a Late Dramatic Win Against Crystal Palace

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