Ranking the top 5 players Chelsea regret losing

Chelsea v Liverpool - Premier League
Chelsea v Liverpool - Premier League

Regret. In the world of football, it is a term that quite often comes to haunt clubs, big or small. It is a sentiment that quite often manifests whenever clubs miss out on key signings, or when clubs let go of current players. It is these very players who go on to do bigger things in their careers than what the club had initially expected of them. It is a fact that clubs, in order to raise capital, do see selling their current players as a viable business model. Clubs such as Borussia Dortmund and Chelsea have even made it the lifeline of their finances. Buying young talent for a relatively cheap price. Later, developing them and selling them for a profit.

Chelsea F.C. has for a long time been a pioneer in this trade. However, as profitable as this model of business is. It involves a huge opportunity cost. The club runs the risk of possibly losing generational talents from their ranks.

On that note, let's take a look at the

Top 5 players Chelsea regret losing


#5 Nemanja Matić

Nemanja Matić had played an incremental role in sealing two league titles for Chelsea F.C. across the 2014/15 and 2016/17 campaigns. Both titles were won under the direction of revered managers such as Jose Mourinho and Antonio Conte. Matić was an important first-team starter under both managers and was truly a midfield general who delivered whenever called upon. He had an immense work rate that saw him drop deep into central defense whenever his team needed the extra protection. He could also be pushed up to be an auxiliary option in Chelsea's attack.

The regret here is, that Nemanja Matić now plays for Premier League rivals Manchester United. He was sold to them in 2017 in a transfer worth up to £40 million. Indeed, the club did make a crisp profit on the trade as they had originally paid £21m to resign him from Benfica (initially he was made part of the deal to bring David Luiz to the club). However, with the club's lack of defensive midfielders in the season after his exit. He will surely be among the players that Chelsea regret selling.


#4 Declan Rice

Dinamo Zagreb v West Ham United: Group H - UEFA Europa League
Dinamo Zagreb v West Ham United: Group H - UEFA Europa League

A proven defensive aptitude and an immaculate holding ability when in possession of the ball. These are the skills that make Declan Rice a coveted midfielder for the top clubs in England. After his splendid performances for the Three Lions at Euros 2021 and a solid domestic season for West Ham. He enjoys a plethora of suitors as he looks to make the step up to a Champions League team.

To add to Chelsea's regrets, Declan Rice was once an academy graduate who was released by the club in 2013. West Ham were quick to snap up his services, with him having progressed through their academy with his ability. He is now an indispensable member of their first-team and a trusted player under David Moyes.

The player is one of the best in his position, presently. West Ham will surely demand a figure around the hundred million pound mark to part with their prized possession. Now that Chelsea are interested in him again, they will surely regret paying a hefty fee for a player who was once part of their ranks.


#3 Romelu Lukaku

Chelsea v Aston Villa - Premier League
Chelsea v Aston Villa - Premier League

Romelu Lukaku was a player Chelsea purchased from Belgian side Anderlecht in 2011. As a teenager, he came to England with a considerable reputation for his physical attributes and goalscoring ability. However, unable to break into the first team at the club. Chelsea decided to loan him to West Brom but ultimately decided to part ways as they later sold him to Everton.

A massive mistake at the time. Romelu Lukaku went on to make history with the respective clubs West Brom and Everton. He put in consistent performances that earned him a big move to Premier League rivals Manchester United in 2017.

Lukaku, having lived up to his name during his time in England. He then moved to Italy to play under former Chelsea boss Antonio Conte and played an imperative role in helping Inter Milan secure their nineteenth Scudetto. During the summer of 2021, Chelsea was convinced of his talent and decided to re-sign him for £97.5mn.

This is yet another instance where Chelsea have regretted paying a huge transfer fee to bring back a player they once let go.


#2 Mohammed Salah

Liverpool v Tottenham Hotspur - Premier League
Liverpool v Tottenham Hotspur - Premier League

Mohammed Salah is probably one of the greatest goalscorers to play for Liverpool F.C. in the modern era. However, in 2014, he was also an attacker in the ranks of Chelsea. He was loaned out to Fiorentino and subsequently transferred to Italian giants Roma after his failure to break into the first team at Chelsea. After a string of important performances, Liverpool came knocking for him and he has not looked back since. Mohammed Salah is now a Champions League winner, and a winner of the Premier League with Liverpool F.C. along with two golden boots to his name.

Mohammed Salah is a player Chelsea should never have sold in the first place considering the impact he has gone on to make in English and European football.


#1 Kevin De Bruyne

Tottenham Hotspur v Manchester City - Premier League
Tottenham Hotspur v Manchester City - Premier League

Kevin De Bruyne, ever since signing for Premier League champions Manchester City, he has been one of the greatest playmakers of this era. Now having a plethora of titles to his name and an insane record of chances created across his seasons in English football, he is surely the biggest player Chelsea regret selling.

At Chelsea, he struggled for minutes under former manager Jose Mourinho. He was then sold to the German side, Wolfsburg, for a mere £16.7 million. The following season he went on to win the German Footballer of the Year award for his remarkable performances in the 2014/15 season. After noting his electric performances in Germany, Manchester City signed him permanently for £55 million in the summer of 2015. He has truly gone on to write history at the club.

Kevin De Bruyne will always be remembered as a superstar that Chelsea let go of too soon.


Quick Links

Edited by Henno van Deventer