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#3 Tiemoue Bakayoko
The 2016-17 season saw plenty of success for Monaco – they won the Ligue 1 title and also made an unlikely run to the semi-finals of the Champions League. That naturally led to their squad being picked apart by Europe’s giants, but while the likes of Kylian Mbappe, Bernardo Silva and Fabinho have gone onto massive success elsewhere, the same can’t be said for Tiemoue Bakayoko.
The Frenchman was a key component of Monaco’s success during the campaign. He played 51 matches in all competitions and his tough-tackling style gave his side some serious bite in the middle of the park.
It came as no surprise when Chelsea parted with around £40m for him, and he quickly found himself in Antonio Conte’s first team when he arrived at Stamford Bridge.
However, to say his career then dipped would be a severe understatement. Bakayoko simply couldn’t seem to cope with the intensity and speed of the Premier League, and the tough-tackling midfielder of Monaco appeared to be gone.
When more and more games went by with the Frenchman looking like a passenger, it became clear he simply wasn’t up to Chelsea’s standards. And against Watford in February 2018, he hit rock bottom – being sent off for two bookable offenses inside 30 minutes.
Bakayoko has since spent seasons on loan at AC Milan and back at Monaco, but despite performing better than he’d done at Chelsea, the hype he garnered in 2016-17 now seems to be gone for good. The truth is that the big move to Stamford Bridge probably came a little too early for him – and he now faces the unenviable task of trying to repair his career before it’s too late.
#4 Pierluigi Casiraghi
While it could be argued that the likes of Drinkwater and Bakayoko saw their careers take a nosedive at Chelsea due to their own faults, the same cannot be said for Pierluigi Casiraghi. In fact, the Italian forward is probably the Blues’ ultimate ‘what if?’ story.
Casiraghi had made his name in Italy’s Serie A throughout the early 1990’s, scoring goals for both Juventus and Lazio, as well as the Italian national team. When the toughness of Serie A’s defences at the time is taken into account, his record of 41 goals in 140 league games for Lazio was highly impressive indeed.
And so when Chelsea boss Gianluca Vialli parted with a then-club record £5.4m for the striker in the summer of 1998, Blues fans were quite rightfully excited. At the age of 29, the Italian was at his peak and was expected to fire Chelsea into title contention.
However, just 10 games into his Blues career, Casiraghi’s luck ran out entirely. In a game against West Ham, he collided with goalkeeper Shaka Hislop and tore the cruciate ligament in his knee. The injury was expected to keep the Italian out for a while, but things were actually far worse.
Casiraghi suffered through 10 operations, but none were able to fully fix his knee, and in July 2000, Chelsea made the call to terminate his contract.
The Italian slid quietly into a sad retirement, and while the Blues were able to receive a £4m insurance payout, it didn’t make things much better for either party – particularly when Casiraghi claimed Chelsea hadn’t offered him any help following his injury.
#5 Andriy Shevchenko
One of the greatest strikers of his era, many fans would argue that Andriy Shevchenko’s career had already begun to dip by the time he joined Chelsea in 2006. But is that really true? The Ukrainian had scored 28 goals in 40 games for AC Milan in the 2005-06 season – a tremendous return by anyone’s standards.
When he arrived at Stamford Bridge though, he appeared to have aged overnight. At 30 years old he should’ve had at least a few more strong seasons in the tank, but despite making 30 Premier League appearances in 2006-07, he looked like a shadow of his former self.
The rumours that then-Chelsea boss Jose Mourinho didn’t actually want him, and that his £30.8m signing was made by Roman Abramovich alone didn’t help, but still didn’t explain his fall from grace completely. His return of 14 goals in 51 games was his worst for years, and his 9 goals in 25 games in 2007-08 were even more disappointing.
By the end of that campaign, Shevchenko was firmly viewed as a big-money flop, and so it came as no surprise when he was sent back to Milan on loan for the 2008-09 campaign. But even that didn’t help him to regain his prior form – he only found the net for his old club on 2 occasions.
Essentially, the Ukrainian’s career took a major dip the moment he signed for Chelsea – and unfortunately for him it was never able to recover.
