As is the case in most of his managerial jobs, things got rather toxic under Jose Mourinho towards the end of his tenure at Spurs. There was a sense that things weren't working out at the club, with the Portuguese boss getting equally frustrated as a result.
In saying that, he did lead the team to the Carabao Cup final. For a side that haven't won any silverware since 2008, that is no small feat.
Of course, Mourinho would not be given the opportunity to take part in that final. He would be sacked by Daniel Levy a few days before the game at Wembley, with Manchester City going on to lift the trophy.
Speaking to Sky Sports, Jose Mourinho has hinted that the nature of his dismissal at Spurs was not befitting of someone with his achievements in the game.
I am in the maturity of my career and also my life where I don't have bad feelings. I just try to accept things the way they are.
It hurt. I take it in a funny way. Every time I speak to English journalists or in a press conference, I make the joke that if I qualify for a final I hope not to be sacked this time.
It is something that doesn't happen to many coaches. This time I cannot say I am a privileged one because it happened to me.
I don't have regrets, I don't have bad feelings. There are a lot of nice people at Tottenham, I wish them the best, even to Mr. Levy.
A guy with my career and my history, it was something strange to happen. In the end it opened the door for me to be in Rome and I'm very happy to be in Rome.
Mourinho has gone on to take the Roma job, leading them to the Europa Conference League final this season.
We imagine that it's likely that he will actually be allowed to take charge of the team on that occasion.