Fook me that's a tough ask m8...
Below Ferguson certainly.
It's almost impossible to meaningfully compare him to managers who were known as much for their tactical innovation as their results - the likes of Michels, Cruyff & Ole.
2 CL wins with (relatively) unfavoured sides is hugely impressive. But on the flip side he spent about half of his career with sides who backed him heavily financially - but he didn't win the CL for any of them.
That said he's won 6 titles across 3 of the top 4 leagues - alongside league wins in Portugal and plenty of domestic (and European 2nd/3rd tier) trophies along the way.
Pep is better stylistically & has a better record but has largely done that as the financially dominant force in each league...or with Messi, which is a quasi cheat code.
The guy I think he's a best match with, in terms of managerial style, is Clough.
I'd have him a notch below Ancelotti - who won league titles in all of Europe's top five leagues while also showing more tactical flexibility and ability to work within whatever constraints he found himself in...without dragging his clubs into civil wars.
I'd prefer Klopp at my club than Mourinho, but clearly his trophy count lags TSO's significantly. Some mitigation that he's always managed sides who have been at a financial disadvantage.
I'd have him above these four
Saachi
Lippi
Heynckes
Capello
As with players, it's a bit tricky to compare him to guys from a very different era - like Paisley etc.
Great question though. I'm sure it'll generate fireworks later in the evening...or when certain bans are lifted