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The Belgian midfielder joined the ranks at Stamford Bridge in January 2012 in a £7 million deal from Genk but after an impressive season on-loan at Bundesliga side Werder Bremen, he made just three Premier League appearances in total before being sold to Wolfsburg.
A year-and-a-half later, he returned to the Premier League and flourished in a Manchester City squad, where he has since become one of the best midfielders in the world. So what really happened at Stamford Bridge that made him want to leave?
De Bruyne has opened up about his time at Chelsea in a fascinating chat with Sky Sports, where he spoke about a "strange" discussion with Jose Mourinho that made him feel like he "didn't have any chance" of playing regular football at the time.
"There was so much in the press about my relationship with Jose Mourinho," the Belgian said.
"But the truth is that I only ever spoke to him twice. The plan was always for me to go on loan for a bit.
"Jose called me into his office in December, and it was probably the second big life-changing moment for me. He had some papers in front of him, and he said, 'One assist. Zero goals. Ten recoveries'.
"It took me a minute to understand what he was doing. Then he started reading the stats of the other attacking forwards - Willian, Oscar, [Juan] Mata, [Andre] Schurrle. And it's like - five goals, 10 assists, whatever.
"Jose was just kind of waiting for me to say something, and finally I said, 'But some of these guys have played 15, 20 games. I've only played three. So it's going to be different, no?'
"It was so strange. I was completely honest. I said, 'I feel like the club doesn't really want me here. I want to play football. I'd rather you sell me.'
"I decided to go away because I felt I didn't have any chances of playing at the time. I didn't see more opportunities coming so for me, it was the best decision to leave Chelsea and go to a situation where I felt I could start again.
"Did I expect it to go this way? Obviously not, because at that time it was a low point in my career but I never had any doubt in my abilities as a football player.
"I can't think what is going to happen eight years down the line playing for City, in World Cups and all that stuff. It's wonderful."
Thoughts on De Bruyne's conversation with then-Chelsea boss Jose Mourinho? The Portuguese manager certainly missed out on the midfielder's talents.
He has shown his true quality time and time again under Pep Guardiola. So far this campaign, the former Chelsea man has scored three times and registered 14 assists in all competitions.
Featured Image Credit: PA
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