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#4 Andre Villas-Boas - £12 million
Andre Villas-Boas is one of the few managers to have led a Premier League club without playing football professionally as a player.
The Portuguese, who was Jose Mourinho's "eyes and ears" during his spell at Porto and Chelsea, found himself in the limelight after he led Porto to a treble (Primera Liga, Portuguese Cup and Europa League) in his first season in-charge in 2010, thanks to the exploits of Radamel Falcao.
At just 34 years of age, he became the Chelsea manager next season, where he replaced Carlo Ancelotti who was paid a compensation of £6 million to vacate the position for the former Porto man.
But just seven months into his new job at the Stamford Bridge, a series of defeats saw the Blues fall out of the top four, which prompted Abramovich to terminate his contract.
He settled his claim with the club for a staggering £12 million, which is just mind-boggling given that Chelsea had paid Porto a world-record £13.3 million to activate his release clause in the first place, just a few months ago.
