4. Carlo Ancelotti (May 2009-May 2011)
Carlo Ancelotti will forever be remembered as the man who brought out the best of a group of Chelsea players from an older generation, giving them the ability to reach for a last hurrah that they deserved.
Ancelloti, who left AC Milan, a club he had both played for and managed, to come to Chelsea, inherited an ageing squad from Hiddink. Such was the magic in Ancelloti’s methods, 30 year old Didier Drogba turned into a goal machine, Florent Malouda sparkled in midfield and John Terry led a commendable back 4, while evergreen Frank Lampard was the engine that drove this side.
Chelsea strolled to the Premier League and FA Cup double, notching up a season goals record of 103 goals on the way. They reached their zenith in their magnificent 8-0 win over Wigan on the final day.
The new season, however, was not so good for Ancelotti. Minimal signings did not bolster a squad no one realized was on its last knees. Goals stopped coming, and a mid-season slump that had become Chelsea’s characteristic over the years refused to end. Fernando Torres, brought in to stem the drought, was a massive, massive failure. Ancelotti was the easy scapegoat. Blamed for being unable to bring the best out of the player he did not really want to sign, Ancelotti was unceremoniously sacked minutes after Chelsea’s final Premier League game, a shock 1-0 loss to Everton, a game that brought down the curtains on a trophyless season.