On the flip side of this argument, i think Mourinho also couldn't win with team who was meant to win...if that makes any sense?
I think the underdog mentality suited prime Mourinho to the tee. Prime Mourinho was indeed super impressive - he also had Chelsea/Madrid playing some great football, albeit they were super dominant in terms of "expensively assembled squads" - and he failed to deliver the UCL with them.
He failed to deliver but notice how Mourinho always goes for a "challenge" and when his team reaches the peak he left it (in this case it was only Porto and Inter). He did not have the opportunity to use the teams he built after they reached the top (sort of did with Porto though).
In Chelsea he had a rising Chelsea and unlimited funds but he had to face the Arsenal invincibles and a very strong Man Utd. He was a newcomer to the league, although this wasn't the hardest job he had he still did a pretty amazing job. He won titles back to back.
He then went to Inter, and be sure Inter had not a realistic ambition to win the CL. The league was sort of certain since Juve went diving and Inter was already champion when he got there but the CL? No one expected Inter to win, he made Inter competitive. And when he got the treble he left for another challenge immediately.
He went to frigging Real, a team with a lot of money but it was facing this little Barcelona Dream Team. Everyone considered Barcelona the best team in the world regardless of the Inter victory and Mou had massive ambition to put his reputation at stake to try to change the order of things in Spain.
He then went back to Chelsea, that was around 3rd-4th place, and tried and managed to get them champions.
Then he went to post-apocalyptic Man Utd, *Spurs* and now Roma.
If he was as Pep has done so far he would simply wait after Real/Chelsea for someone else like PSG invite him as they absolutely would.
Exactly. Wherever he was he had money at his disposal. Sure, the thing he did with Porto was great but Porto wasnt exactly a minnow.
No one cares that Mou won the portuguese league with Porto, people care that Porto (much poorer than the favourites) won the CL (and the UEFA cup to a lesser degree), that is so obvious