Don't only focus to the trophy to benchmark Levy's success with Tottenham. You better also consider how he made Tottenham's financial became very sustain. He also helped the club to growth from 80m valuation club to the more than 1b valuation club. Despite only winning two trophies in his 25 years with Tottenham, He achieved a lot of things in different thing.
Yeah maybe he managed team finances nicely but that's not enough for Tottenham fans for sure.

They have been expecting more. Because this team really has a bigger potential.
For 5 years, they have been spending at least around 200 million euros yearly for transfers. But they can't have successful seasons most of the time.
Wasn’t he a better vision chairman during his stay at Tottenham Hotspur. I don’t think during his 24 years stay as the executive chairman of the club has anytime had him getting the club relegated from the premier league. He has achieved some success and has been very impressive for him at the club. Some chairman’s most have spent longer time than he did in one club and are yet to win any trophy, so it’s a good one for him to have won two trophies during his time in the club. Participating in about 18 European competitions in the last 20 years is a great achievement for the club.
They could have relegated last season by the way, don't forget about it.

They must be thankful for the teams in the relegation zone for being much more horrible than them.
I don't see any impressive success other than winning a Europa League trophy. Even that took them too long with such money power.