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#3 Danny Drinkwater | Leicester City to Chelsea, £35m
Chelsea signed both Leicester City's Premier League-winning midfield stars N'Golo Kante and Danny Drinkwater in the span of one year. They were at the heart of the Foxes' unlikely title charge and powered the side with their industry in the middle of the park. While the former is still regarded as one of their best players, the latter is currently winding down his contract in Istanbul.
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On the back of helping Leicester City to their first-ever appearance in the UEFA Champions League quarter-finals, Drinkwater became the tenth-most expensive Englishman of all time as Chelsea paid £35m for him on a £100,000-a-week contract. Unfortunately, the move brought his career to a standstill as Drinkwater went on to make only 23 senior appearances for the Blues, with only 12 coming in the league.
After failing to break into the side, the former Manchester United man was subsequently sent out on loan spells at Burnley, Aston Villa, and Kasimpasa. Having cost Chelsea a total figure of over £50m in transfer fees and wages, Drinkwater's move to Stamford Bridge is one of the most disastrous transfers in the Abramovich era.
#2 Andriy Shevchenko | AC Milan to Chelsea, £30.8m
Roman Abramovich sent shockwaves across Europe when he broke the English transfer record to sign Andriy Shevchenko for £30.8m in 2006. The transfer was also surrounded by a lot of controversy at the time as Jose Mourinho did not want Chelsea to sign, but Abramovich went against his manager's wishes and brought him to Stamford Bridge.
The 2004 Ballon d'Or winner arrived in West London amidst a lot of fanfare, and was handed his preferred #7 shirt. However, it was far from a successful move for Shevchenko or, indeed, for Chelsea. The Ukrainian was regarded as one of the deadliest strikers of his generation but he failed to reach those heights in a Chelsea shirt, scoring just nine goals and setting up a further eight in 48 league games.
After a forgettable debut campaign for the club, Shevchenko returned to the Rossoneri on a loan deal before a homecoming at Dynamo Kyiv. However, the striker — who remains the second-highest AC Milan scorer of all time — never managed to replicate his heroics from the past since moving to Chelsea. In many ways, he was one of the first major big-money disasters in the Abramovich era.
#1 Fernando Torres | Liverpool to Chelsea, £50m
Two years after Shevchenko departed the club, Chelsea announced the signing of one of the best strikers in world football at the time, Fernando Torres. The Blues broke the British record fee and made Torres the most expensive Spanish player of all time when they signed him for a staggering £50m to bolster Carlo Ancelotti's attack.
The World Cup winner was one of the best players in the league during his time at Anfield. However, the blockbuster move to Chelsea was the beginning of his tragic downfall as Torres endured a nightmare spell at Stamford Bridge. He looked nothing like the devastating centre-forward he was at Anfield, struggling to score even the easiest of chances for the Blues. Torres had just 45 goals to show for across 172 games for Chelsea in all competitions.
Torres' open-goal miss against Manchester United was, perhaps, a moment that perfectly summed up how poorly he fared at Chelsea. The Spaniard then left on loan to AC Milan which was made permanent, before eventually returning to his boyhood club Atletico Madrid. However, he never managed to recapture the stunning goalscoring ability that made the world fall in love with El Nino.
In many ways, Torres' failure at Chelsea is regarded as the most disastrous high-profile transfer in the Abramovich era. The ex-Liverpool man and Shevchenko were the first of many strikers to fail at Chelsea, including Alvaro Morata, Gonzalo Higuain, and Radamel Falcao, among others.
Also read: 5 Transfers that dramatically changed the fortunes of a club
