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#3 Andriy Shevchenko – AC Milan to Chelsea (£30.8m), May 2006
For the best part of a decade, Andriy Shevchenko was renowned as one of Europe’s most feared strikers. The Ukrainian plundered goals against practically any side he faced, helping both Dynamo Kyiv and AC Milan to massive success in the late 1990s and early 2000s.
By the summer of 2006, however, at the age of 30 and with plenty of miles behind him, Shevchenko had begun to slow down somewhat. That made it all the more surprising when Chelsea parted with over £30m to bring him to Stamford Bridge, despite boss Jose Mourinho seemingly not really wanting him.
Fans immediately suspected Shevchenko’s signing was a vanity project from owner Roman Abramovich, and results on the pitch appeared to back that theory up.
Shevchenko just couldn’t produce his best form at Stamford Bridge, ending his debut season with just four Premier League goals to his name.
The 2007-08 season saw him fare no better despite Mourinho’s departure midway through, as the Ukrainian scored just eight goals in all competitions. And by the time 2008-09 rolled around, it came as no surprise to see him sent back to AC Milan on loan.
When that loan spell ended, Shevchenko was still surplus to requirements at Stamford Bridge and ended up moving back to Dynamo Kyiv on a free transfer.
To call his signing an expensive mistake by Chelsea would be an understatement.
#4 Kevin De Bruyne – Chelsea to Wolfsburg (£18m), January 2014
Younger Chelsea fans might dream of a Blues side including Mohamed Salah and Kevin De Bruyne, but incredibly, that team could’ve been a reality had serious mistakes not been made.
The Belgian assist king – who has won seven major trophies with Manchester City, including two Premier League titles, had a very brief stint with Chelsea in the 2013-14 season.
However, he was never given a fair chance to succeed and ended up leaving Stamford Bridge for just £18m after making only a handful of appearances.
De Bruyne was signed by Chelsea from Genk in January 2012, but part of the agreement meant he remained in Belgium toll the end of the season. And when the 2012-13 campaign came around, the midfielder became part of Chelsea’s infamous 'loan army', moving to Werder Bremen for the season.
De Bruyne did well in Germany, scoring ten goals and registering nine assists, but evidently, it wasn’t enough to convince Chelsea of his talent.
He was given just nine games – three in the Premier League to prove himself at Stamford Bridge before he was sold to Wolfsburg midway through the 2013-14 campaign.
From there, De Bruyne instantly proved his class by performing remarkably for the German side. After scoring ten goals and registering 20 assists in 2014-15, Manchester City parted with £55m to bring him to the Etihad.
Every Premier League fan knows what has happened from there. Seven years after selling him, the treatment of De Bruyne must go down as one of Chelsea’s biggest transfer blunders.
#5 Danny Drinkwater – Leicester City to Chelsea (£35m), September 2017
Chelsea’s signing of midfielder Danny Drinkwater was always a head-scratcher, with many fans expecting to see him end up on a list like this from day one. And unfortunately for Drinkwater, his career at Stamford Bridge has basically proven his doubters correct.
The midfielder had performed tremendously for Leicester City in their 2015-16 Premier League title-winning campaign. If he had moved to a bigger club that summer, it probably would’ve been understandable.
But Drinkwater remained at the King Power Stadium for the 2016-17 season and – like Leicester City– his performance level dipped pretty dramatically.
That’s why it was such a surprise to see Chelsea decide to part with £35m to bring him to Stamford Bridge, despite not really needing to add a midfielder in what was already a top-heavy squad.
It came as no surprise to see Drinkwater make just 12 Premier League appearances for the Blues in the 2017-18 campaign. But nobody could really have expected things to get even worse for him.
Drinkwater failed to make a single competitive appearance for Chelsea during the 2018-19 campaign, as he was frozen out entirely by Maurizio Sarri. And loan moves to Burnley and Aston Villa in the 2019-20 season were disastrous too.
In the first, he made just two appearances, as he spent most of the time injured after becoming involved in a drunken nightclub brawl. And while he doubled that number with Villa, his time there ended in disgrace after he headbutted teammate Diogo Jota during a training session.
Drinkwater is currently on loan with Turkish side Kasimpasa, but at the time of writing, he’s made just three appearances for them. Even by Chelsea’s standards, the signing of the former Leicester City midfielder stands as a truly colossal mistake.
