The story goes that Jose Mourinho and Jimmy Floyd Hasselbaink only saw each other once when the new manager came into Chelsea in 2004 before he was sold, although this is a decision he would later admit he regretted.
Mourinho put an end to a 50-year wait for a league title at Stamford Bridge in his first season in charge, and had plenty of firepower to rely on in his squad.
Didier Drogba and Eidur Gudjohnsen were the main source of goals up front, while Frank Lampard had started to really earn his stripes as an impactful midfielder in front of goal.
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Jose Mourinho admitted to Jimmy Floyd Hasselbaink he made a mistake in selling the striker
There was no real room for Hasselbaink, who had been with the club since 2000 and been extremely successful at Stamford Bridge.
The Dutchman has now told ‘Clutch 9’ that after he had left the Blues, Mourinho admitted to him that he had made a mistake letting him go.
Jimmy Floyd Hasselbaink
17 Feb 2002: Jimmy Floyd Hasselbaink of Chelsea celebrates scoring a goal during the AXA sponsored FA Cup fifth round match against Preston North End played at Stamford Bridge, in London. Chelsea won the match 3-1. Mandatory Credit: Ben Radford /Allsport
He said: “So he still had four strikers and he must have thought Kezman is better than Hasselbaink or whatever.
“He never spoke to me, never said anything. Afterwards when I left Middlesbrough and I did well at Middlesbrough, he did say ‘I’ve made a mistake’ but it is what it is, isn’t it?”
Hasselbaink had scored 87 goals in 177 games for Chelsea across four seasons, including two campaigns where he scored 23 league goals.
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Mourinho’s Mateja Kezman gamble really didn’t pay off
One of the four strikers left in the squad for the 2004-05 season was Mateja Kezman, although this would quickly turn out to be one of the manager’s rare errors at the time.
He managed just four goals in 25 league games, and was sold the following summer to Atletico Madrid.
Having Hasselbaink alongside Drogba and Gudjohnsen would have allowed for incredible depth in the striker position, likely allowing the Blues to make more of a challenge on all fronts.
Despite their league success, they went out of the FA Cup in the fifth round, and exited the Champions League in controversial circumstances at the hands of Liverpool.
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