10 Biggest Dodged Bullets In Chelsea Transfer History

9. Emmanuel Adebayor

Back when Adebayor's lousy attitude had landed him in hot water with Arsene Wenger, who packed him off to Manchester City for the deeply silly fee of £25 million, new Chelsea manager Carlo Ancelotti was supposedly waving his sensual eyebrows in the direction of the Togolese forward. In fairness, Adebayor had proven he could be a devastating weapon when he wanted to be, having hit 30 goals in his penultimate season with the Gunners. Unfortunately, even the slightest hint of discontent was enough to render him almost entirely useless, prone to ambling around the pitch before getting sent off after an hour. City got 14 goals out of him in his first season, in addition to a sending off for violent conduct and a tacky incident where he celebrated a goal against Arsenal in front of his former fans. Not much of a return on such a lofty transfer fee and Edin Dzeko, Mario Balotelli and Carlos Tevez (because the top search term for Man City targets in those days was 'insanely temperamental') came in the following season to replace him. His loan move to Real Madrid failed to spark and like all big club rejects, he eventually ended up at Tottenham, having impressed on loan to win his contract before spending the subsequent years doing his best to become the first person to ever fall asleep in the middle of playing a Premier League game. Much as I love Carlo Ancelotti, it's a huge relief he didn't get his man on that occasion.