Winning a cup competition should actually change nothing for Ole or any manager for that matter.
And that's simply because winning a cup competition is purely based on luck. Hell, look at teams Chelsea have faced in CL this year, and what we faced in GS this year. I don't think any of Sevilla, Atleti, RM and Porto are stronger than PSG (who we faced in GS) and one can argue that there isn't a lot to differentiate between the current RM side and Leipzig as well if you look at performances (RM would be slightly ahead, but the gap would be negligible). Hell, some of our EL opponents have been better than the teams Chelsea have faced in KO rounds - Milan for example.
Similarly, the teams we faced when we won EL was absolute dross. And winning then shouldn't be counted as some achievement that "We're there".
The logic is really simple - if you're not convinced by Ole so far, that's on you and some weird bias you have, and ideally EL win shouldn't be what that changes your opinion .In that case result in a single game is what is shaping your opinion