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From Shevchenko To Lukaku: The Top 5 Worst Chelsea Signings Of All Time

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From Shevchenko To Lukaku: The Top 5 Worst Chelsea Signings Of All Time

Chelsea over the years have reaffirmed their transfer pedigree by making big statements in the market each season. However the increasing rate of inflation in football opens the door to clubs making gambles and some big fees backfiring on players who simply can’t live up to their price tags. 

With controversy surrounding their club-record signing of Romelu Lukaku and his loan departure to Inter Milan after just one season at the club, it poses the question as to what are the worst five signings Chelsea have made?

A general view of a Chelsea crest sign at Stamford Bridge. (Alamy)
A general view of a Chelsea crest sign at Stamford Bridge. (Alamy)

5. Andriy Shevchenko


In May 2006, Chelsea hit the headlines by breaking the English transfer record by splashing £30.8 million on AC Milan and Ballon d’Or winner Andriy Shevchenko

The Ukrainian joined the Blues as Jose Mourinho and Roman Abramovich continued to make massive statements in the market with hopes of reinforcing the attack. However the transfer stagnated as Shevchenko failed to find consistent form and was often benched. 

His 2006-07 season was heavily hampered with injury and by the time of his return the damage was done, the former Ballon d’Or winner was a shadow of the player the Blues had dreamt of and arranged a loan move back to AC Milan in 2008. Shevchenko managed a measly nine league goals in west London as he struggled to compete with Didier Drogba

4. Tiemoue Bakayoko


After playing a pivotal role in AS Monaco’s famous Ligue 1 triumph in the 2016-17 season, Tiemoue Bakayoko was signed for £40 million to replace Nemanja Matic who was reunited with Jose Mourinho at Manchester United in the summer of 2017. 

Tiemoue Bakayoko of AC Milan during warm up before the Serie A match against Atalanta. (Alamy)
Tiemoue Bakayoko of AC Milan during warm up before the Serie A match against Atalanta. (Alamy)

It didn’t take long for Chelsea fans to realise that the Blues had drawn the short straw with Monaco also selling the likes of Kylian Mbappe and Bernardo Silva. 

Bakayoko’s lack of technical attributes shocked supporters as his ability to lose possession ironically contradicted supporters' chants that ‘he never gives the ball away’. 


Notably, his performance versus Watford is still talked about amongst fans as the single worst individual performance for Chelsea with the Frenchman managing to lose all composure in midfield before picking up two first half yellow cards in a 4-1 loss at Vicarage Road. 

A silver lining to the deal is that Chelsea have managed to recoup a significant amount of money through loan deals to Napoli, AS Monaco and AC Milan as the club still look to move the Frenchman on permanently this summer.

3. Danny Drinkwater


After the highs of winning their fifth Premier League title, the summer of 2017 was one to forget for Chelsea as the Blues forked out a whopping £30 million for Leicester’s Danny Drinkwater on deadline day. 

Antonio Conte had initially shown intent to sign then Arsenal player Alex Oxlade-Chamberlain but had to settle for Drinkwater after Oxlade-Chamberlain expressed his reluctance to feature as a versatile right wing- back. 

The main downside to the Drinkwater transfer was the five-year deal the Blues were locked into. At £100,000-a-week, Drinkwater featured 12 times in the Premier League and was embroiled in off the pitch incidents which further marred the disastrous move to the capital. 

He experienced four loan deals over the course of his contract with his debut for Aston Villa resulting in a 6-1 defeat where he was dribbled past six times. 


After five years, he was confirmed to be leaving Chelsea at the end of his contract this summer.


2. Kepa Arrizabalaga

Signing from Athletic Bilbao in 2018, Kepa was a last minute replacement to the departed Thibaut Courtois for a staggering £72 million. 

After his €20 million release clause expired in January, Chelsea were forced to pay well over the odds for the Spanish international and gave him the number one shirt at the start of Maurizio Sarri’s one and only season in west -London. 

After a solid start to his Chelsea career, Kepa’s tenure was heavily marred by his actions in the 2019 Carabao Cup final where he refused substitution and was substandard in the following penalty shootout.

Under Frank Lampard, Kepa played his part in the worst Chelsea defence since the turn of the century conceding 54 goals with a shocking save percentage of 54.5 percent which statistically made him the worst Premier League Goalkeeper in history. 

Upon the arrival of Edouard Mendy it looks next to impossible for the Spaniard to break into Thomas Tuchel’s XI with the Blues being reported to be willing to loan Kepa to Sarri’s Lazio. An absolute transfer howler.

Kepa Arrizabalaga on pre match training of Super Cup Chelsea vs Liverpool. (Shutterstock)
Kepa Arrizabalaga on pre match training of Super Cup Chelsea vs Liverpool. (Shutterstock)

1. Romelu Lukaku

Last summer's transfer of Romelu Lukaku felt destined for greatness. The football world held their breath as the striker completed his move for a record £97.5 million to the club who initially brought him to England nine years prior. 

After providing fans with a series of promises and quotes alongside a strong start to life back in England, he took part in an unauthorised and astonishing Sky Italia interview last December. 

Lukaku’s form never recovered and most importantly his relationship with Chelsea and Thomas Tuchel began to deteriorate as supporters felt anger at the entitlement and lack of loyalty he’d shown to a club he had claimed to love months before. 

Lukaku registered a pitiful eight league goals and fell out of favour under Tuchel who preferred Kai Havertz up top. 

Inter are close to confirming a loan deal for Lukaku which would put an end to a torrid ten months back in England.

Chelsea versus Chesterfield: Romelu Lukaku of Chelsea. (Alamy)
Chelsea versus Chesterfield: Romelu Lukaku of Chelsea. (Alamy)

With the departure of key players this summer, over the next two months Chelsea will be active in the transfer market to rebuild the spine of their team. 

With the club being desperate to close the gap to Liverpool and Manchester City, it is important that the new additions are the right ones and don’t add to the list of failed signings at Stamford Bridge.

Featured Image Credit: Alamy

Topics: Chelsea, Romelu Lukaku, Danny Drinkwater, Kepa Arrizabalaga

Reuben Rosso
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