#3 Baba Rahman
He was a disastrous signing that set the tone for Chelsea's shambollic defence of their Premier League title in August 2015. Baba Rahman was signed for a zealous 14 million fee as a promising fullback from Augsburg.
He managed to string together 15 appearances in Chelsea colors and was vastly out of depth and pace with the frantic intensity of the Premier League. Mourinho was vocal about his and Papy Djibodji's quality to play for Chelsea.
Somehow, Baba Rahman remains on the books of the club for nearly 6 years with just 23 appearances in between. He has been sent out on globetrotting loan spells to the likes of Reading, Schalke, Reims, Mallorca and PAOK, all the while still being paid partially by Chelsea.
#2 Khalid Boularhouz
He was a fully fledged Netherlands international, playing in four major tournaments for the Oranje. Khalid Bhoularouz had all the makings of a misplaced transfer for Chelsea, right from the moment he wore "Number 9" as a centre back.
Signed by Jose Mourinho who was impressed by the lanky Dutchman's mobility and versatility, Boulahrouz had a largely "start-stop" Chelsea career. Plagued by injuries and just having to compete with world class defenders for a starting position, Boulahrouz was up against it from the very start.
Then came a debilitating knee injury that put to rest his hopes in Chelsea blue. he was shipped out to Sevilla, where he made just 6 appearances before being permanently sold to Stuttgart for a paltry 5 million fee.
#1 Asier Del Horno
The Spanish fullback arrived in London to shoulder great expectations of becoming a Chelsea regular in the left back slot. Rapid, robust in the tackle and technically adept for Atheltic Bibao, Chelsea snapped up the then 24-year-old for a £8.4 million fee in 2005.
It's hard to designate a league-winning fullback as a complete flop for Chelsea. But Del Horno's only season at Chelsea was largely forgetable despite making over 25 appearances. Sadly, the most memorable moment was the Champions League tie against Barcelona where he was run ragged by a teenage Lionel Messi. He was sent off for a rash challenge that defined his Chelsea career.