Football stories can be full of surprises sometimes even great managers look back and wish they had made a different choice. This is what happened between Jose Mourinho and Jimmy Floyd Hasselbaink at Chelsea. Years after selling the striker, Mourinho told Jimmy that letting him go was a mistake. That simple moment has become a story many fans still talk about today.
🗣️ Jimmy Floyd Hasselbaink: "Jose [Mourinho] came to the club in 2004 and basically said that I could go.
There wasn’t a phone call or anything like that from him. Peter Kenyon [then Chelsea chief executive] called my agent but that was about it.
I’ve seen him since and he’s… pic.twitter.com/yqal2WV8Bi
— Vince™ (@Blue_Footy) January 9, 2025
Jose Mourinho and Jimmy at Chelsea
When Jose Mourinho came to Chelsea in 2004, he arrived with big confidence. He had just won the Champions League with Porto. He told everyone he was special and ready to win in England. Chelsea had not won the league for 50 years fans were excited and hopeful.At that time, Jimmy was already a star at Chelsea. He had joined the club in 2000 he scored many goals and became a fan favorite. In four seasons, he scored 87 goals in 177 games. Twice he scored 23 league goals in a single season that is a great record for any striker.
But football can change very fast when Jose Mourinho started building his new team, he made some big decisions. One of those choices was to sell Jimmy many fans were shocked. They knew how important Jimmy had been for the club. Still, Mourinho believed he had enough attacking players.
Chelsea signed Didier Drogba that summer Eidur Gudjohnsen was still at the club Mateja Kezman also joined the team. Mourinho felt these players could lead Chelsea to success. So Jimmy had to leave even though he had done so much for the club.
Why Jose Mourinho Told Jimmy It Was a Mistake
The story did not end there after leaving Chelsea, Jimmy joined Middlesbrough. He continued to score goals and showed that he still had great quality. He worked hard and proved he could perform in the Premier League.Later, Jimmy shared something very interesting he said that Jose Mourinho admitted he had made a mistake. Mourinho told Jimmy that selling him may not have been the right choice that is a strong thing for a manager to say.
At Chelsea, Mateja Kezman struggled to score he managed only four league goals in 25 games during the 2004 and 2005 season. That was not what the club expected. Meanwhile, Chelsea won the Premier league title in Mourinho’s first season. It was a huge achievement and ended a long wait for the fans.
Even so, some people believe Jimmy could have helped even more. Chelsea were knocked out of the FA Cup in the fifth round. They also lost to Liverpool in the Champions League semi final. Those were close and painful matches. With another proven goal scorer like Jimmy, things might have been different.This story shows that football decisions are not always simple. A manager must think about team balance, tactics, and the future. Sometimes a choice looks right at the time but feels wrong later.
Jimmy Floyd Hasselbaink: Jose Mourinho told me he made a ‘mistake’ selling me at Chelsea.

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… pic.twitter.com/5Qq7PN4cJX
— I_@m_Sepp (@seppchelsea) February 27, 2026
Fans’ Reactions and Impact
Fans still discuss this moment today some say Mourinho needed to refresh the squad and build his own team. Others feel Jimmy deserved more respect after his great service. Both sides have strong feelings.
What makes this story special is the honesty Jose Mourinho is known for his strong personality he rarely shows regret. But telling Jimmy that he made a mistake shows humility it reminds us that even the best managers are human.
Author’s Opinion
In the end, Blues won trophies and created history under Mourinho. Yet the memory of Jimmy’s exit remains an interesting chapter. It teaches young fans that football is not just about winning. It is also about choices, respect, and learning from the past. Even champions can look back and wish they had done one thing differently.
As featured on Chelseanews.com
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