Charismatic and polarising football coach José Mourinho always has one single goal for his teams: to win, no matter what. It’s this mentality that led him to awards, accolades, and admiration. So what happens when the winner stops winning?

This second and final episode on José Mourinho chronicles his fall from grace in the 2010s. Simon and Mehreen cover his arrival at Real Madrid in 2010 to joining Turkish football club Fenerbahçe in 2024—and how Mourinho turns toxic when he’s no longer at his peak winning streak.

Simon and Mehreen cover this new, more uncomfortable era for Mourinho—a time when aggressive coaching styles dominate, and awareness of men’s mental health becomes more mainstream. How does Mourinho adapt (or not adapt) during his tenures at Chelsea, Manchester United, and Tottenham Hotspur?

And is it really over for the notorious media star, love bomber, and genius strategist, or are we now entering Mourinho’s post-Roma redemption era? Listen to find out.

This is a two-parter; listen to our first episode on the rise of José Mourinho before this one.

Time stamps:

00:36: Welcome back

04:37: Arrival at Real Madrid

09:30: Spurring on the Real Madrid-Barça rivalry

14:45: An emotional loss (ft. two emotional Portuguese men)

18:11: The end of the Real Madrid ‘revenge tour’

19:24: Return to Chelsea and love bombing

27:43: Downfall at Chelsea, and the Justin Bieber incident

33:50: Mourinho struggles at Manchester United

40:33: Mourinho’s Manchester United gets left behind

44:35: An ill-fated tenure at Tottenham Hotspur

48:10: A hero’s welcome at Roma (and the start of redemption?)

50:04: Chasing dopamine at Fenerbahçe and Turkish football

53:40: Mourinho’s future and legacy

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