Roy Keane ITV
Roy Keane spent the bulk of his career working for arguably the greatest manager of all time. Indeed, under Sir Alex Ferguson, the Irishman achieved enough to become a Manchester United legend.
Most notably, he won the Premier League on seven occasions, while he also lifted the Champions League in 1999. All of his success at Old Trafford came under Sir Alex and the pair enjoyed great success but ultimately fell out, leading to Keane's exit in 2005.
With his fiery personality, it's fair to say the former Man United captain did not get on well with everybody he worked with during his career. Famously, former Republic of Ireland boss Mick McCarthy sent him home from the 2002 World Cup training camp after their pair clashed.
Having the right manager can be crucial for any player, but for Keane, it perhaps mattered more than most. The player himself has even admitted he wouldn't have been that happy to play for one Premier League legend.
Keane Wasn't Keen on Jose Mourinho
"He plays too many mind games"
As quoted in 2014, he revealed that there may have been issues had he ever been coached by Jose Mourinho. He may well be one of the finest managers to ever work in the English top-flight, but Keane didn't think they'd go well together:
The pair had a bit of a public tiff while Keane was working as a Premier League coach in 2014. At the time, Mourinho had a ritual of shaking the opposing manager's hand before the final whistle went. But when the Chelsea boss went to greet Aston Villa manager Paul Lambert and his assistant Keane, he was snubbed.
Speaking after the game, which Villa list 3-0, Keane said per the Guardian: "The game is still going on. You wouldn’t do that on a Sunday morning, you would get knocked out.
“I don’t mind all that [mind games] but the game is still going on. It’s disgraceful. I’ve seen him doing it to other managers; it is a disgrace.”
When asked whether Mourinho’s actions were arrogant and disrespectful, Keane replied: “What do you think? That’s a stupid question.”
Mikel Arteta
Keane Preferred Two Premier League Bosses
Pep Guardiola and Jurgen Klopp
After talking about how he wasn't keen on working for Mourinho, he went on to claim Pep Guardiola might be better suited to him. Of the Manchester City boss, he said: “If I was still a player today, I’d like to think I could work with Pep Guardiola. I like his style, and his presence, and the way he conducts himself.”
That's not the first time Keane has named a modern Premier League legend as somebody he would have liked to have played for. Indeed, he added Jurgen Klopp to his personal list, explaining in 2024:
"He's also missed out and been close. This is a proper rollercoaster for him and one of his strengths is that he's an emotional guy. We see that on the sideline with him. He's a very honest manager and I don't think he plays too many games. He's not like this robot after games where he's almost just media-trained.
"He seems a very honest manager and I always try to picture if I was a player back in the day, I think I'd like to play for this guy."