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#3 Yossi Benayoun
Yossi Benayoun was signed by Chelsea after impressing for West Ham United and Liverpool. Benayoun was a versatile midfielder, capable of serving in more than three positions. One of Israel's greatest footballers, he scored 29 goals in 134 appearances for Liverpool before joining the Blues for £5.5 million.
In just a single season at Chelsea, Benayoun chalked up just two assists and a goal in 24 matches. He was a far cry from the creative player under Rafa Benitez at Liverpool who even registered a Champions League hat-trick.
Wearing the number 10 for Chelsea, which he soon gave up to Juan Mata, Bennayoun was sidelined as a utility player. He even went out on loan to arch-rivals Arsenal.
After leaving Stamford Bridge, he went on to play for West Ham and Queens Park Rangers.
#2 Tiemoue Bakayoko
Tiemoue Bakayoko was heraled by many as an exciting talent and was compared to box-to-box greats such as Patrick Viera and Yaya Toure. Bakayoko burst onto the scene as a part of Monaco's now cult status team of 2016-17 alongside the likes of Kylian Mbappe and Bernardo Silva.
Eyed as a replacement for Nemanja Matic, he arrived at Chelsea for a £40 million fee. Bakayoko started well under Antonio Conte but was quickly at the heart of Chelsea's disastrous collapse in the season after they won the Premier League title. His awful performance and red card in under 30 minutes during a defeat against Watford in particular caused great resentment amongst fans.
After two consecutive poor seasons at Stamford Bridge, he was dispatched out on loan to Italy. Bakayoko had spells with AC Milan, Monaco, Napoli and AC Milan once again, while still being on Chelsea's books. Earlier this summer, he joined the Rossoneri on a permanent deal.
#1 Danny Drinkwater
This was a bizarre transfer particularly for the almost ridiculous £35 million fee. But it's also weird because Chelsea didn't really need Danny Drinkwater. They had already signed his more effective former midfield companion, N'Golo Kante, the previous summer.
Drinkwater arrived on the back of Antonio Conte's tumultuous season defending Chelsea's Premier League crown. He looked very much out of his depth in a midfield that had the likes of Cesc Fabregas as an alternative. Understandably, Drinkwater was quickly relegated to the reserves.
An expensive mistake, the former Leicester City man found himself a reluctant part of Chelsea's "loan army." He has been loaned out to the likes of Burnley, Aston Villa and Kasimpasa, and is currently at Reading.
Drinkwater quite often found himself in no man's land with Chelsea's reserve team too. He made headlines last year when he was handed a straight red after a bust up in a U-23 game. The only real high point for Drinkwater with Chelsea was his first goal, which was a screamer against Stoke City.
