André Villas-Boas took charge at Stamford Bridge in June 2011, and lasted only until 4 March 2012, when Roman Abramovich sacked him with Chelsea fifth in the Premier League and facing elimination from the Champions League after a 3-1 first-leg defeat at Napoli.
Roberto Di Matteo, his own assistant, was promoted to interim manager and went on to win the FA Cup and the Champions League before the season was out, finishing only sixth in the league.
Speaking on the Obi One Podcast, hosted by John Obi Mikel, Villas-Boas, now 48, said the way Di Matteo's appointment unfolded still troubles him.
“For me, it was very very difficult to see Roberto take the job. It was something I felt dearly because I was the one who chose him. Chelsea wanted a different person, particularly Marina Granovskaia (director) and Roman (Abramovich, owner).
“They chose him for the football style at West Brom. For me, I told him this, for me not to have known he was given the job was something I wasn't expecting from him.”
Asked whether Di Matteo had told him in advance, he said: “No. I don't know if Chelsea hierarchy had something planned and it ended up a different way because of the results he was getting, but it is what it is.
"Football is a dynamic environment, it changes from fixture to fixture, and it is what it is. I think that was probably the biggest disappointment.”
His account follows a story former captain John Terry told in 2024, on Up Front with Simon Jordan, about a pre-season tour of Asia in which Villas-Boas seated academy players Josh McEachran and Nathaniel Chalobah in first class while senior stars, including Frank Lampard, were moved down the plane.
“We've got Josh McEachran, Nathaniel Chalobah, a couple of other young players all in first class,” Terry said. “And this was part of AVB going 'no player is bigger than me, everyone's the same.' It turns out Lamps is flying out in first class and I'm flying back in first class. So if you fly out in first, you come back in economy, but basically it wasn't good enough.”
Villas-Boas disputes some of the details.
“First of all, we are speaking first class or business class, not economy. I have seen the story, it is good you point it out to me, this is me as a principle human being, setting out the rules.
“We only had a few free in first class, we couldn't fit all the first team players, you would have to make a selection between say Cech, Drogba, Terry, Lampard, then leave out the rest of the boys. The principle was that - instead of creating a problem, let's put the academy boys here and send the rest of them to business class.”
Villas-Boas has consistently credited Di Matteo and the players, rather than himself, for the Champions League win that followed his exit, most recently telling the podcast he could not bring himself to support Chelsea in the final against Bayern Munich.