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#3 Ashley Cole - £5 million + William Gallas
Ashley Cole's transfer to Chelsea was full of controversies, but it eventually ended with him making a switch to west London for £5 million plus William Gallas.
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It proved to be an absolute bargain for Chelsea as the former Arsenal man during the peak of his powers after being part of the Gunners' 'Invincibles' squad.
The English international spent eight glorious seasons at Stamford Bridge, winning every major honor possible during his time at the club. The left-back managed to win the Premier League under Ancelotti while he also won the Champions League and Europa League in back-to-back seasons. He also won four FA Cups at Chelsea, adding to his previous three with Arsenal, while also winning the English League Cup with the Blues in 2007.
Cole made 338 appearances across all competitions for Chelsea, registering seven goals and 38 assists during that time. He eventually left the club to join Roma in 2014 before hanging up his boots at Derby County in 2019.
Cole is widely considered to be the best ever Premier League left-back, if not the best of all time.
#2 Michael Ballack - Free
In the summer of 2006, Michael Ballack became a free agent after leaving Bayern Munich and a host of top clubs were behind his signature. It was Chelsea who secured his signing ahead of the likes of Manchester United to make it one of the greatest free transfers of all time.
The German midfielder managed to make 167 appearances for the Blues during his four-year spell at Stamford Bridge, registering 25 goals and 24 assists during that time. He scored some crucial goals for Chelsea, including a match-winning goal against Porto in the Champions League Round of 16.
The former Germany captain left the Blues in 2010 with five major honors to his name, which included three FA Cups, one League Cup and a Premier League title.
Although Ballack was generally behind Frank Lampard in the pecking order, he is fondly remembered by Blues fans for his crucial contributions at the club.
#1 Cesar Azpilicueta - £6.5 million
Nicknamed "Dave" by the Chelsea faithful, Cesar Azpilicueta has become a fan favorite since moving to Stamford Bridge and is now the club's captain. Arriving for just £6.5 million from Marseille in 2012, the Spaniard has perhaps proved to be the biggest bargain in the Premier League's recent history.
Used as a squad player during his first season, the Spaniard became the first choice left-back after the arrival of Jose Mourinho in 2013. Although a right-back, Azpilicueta excelled in that position and played a vital part in Chelsea's 2014-15 league title win.
Antonio Conte's arrival then saw him being used as a right centre-back in a 3-4-3. Azpilicueta excelled in that role as well, helping his side clinch another Premier League title.
Azpilicueta later became club captain at the start of the 2019-20 season and led Chelsea to the Champions League title last term, cementing his status as a true legend of the club.
The 32-year-old is currently seventh on Chelsea's all-time appearance list and is considered one of the Premier League's best ever full-backs.
