Yeah Tottenham had their chance to go stellar a couple of years back but faltered in their Premiership chase and their Champions League demise. I can see them falling away from the top again and become sub top again. Arsenal on the other hand are going in the right direction. I am really looking forward to see if Ole can keep the momentum going.
One thing that is missed out by most is that Tottenham are one of the bigger clubs hit hardest by the pandemic. You've finally opened one of the best multi-purpose stadiums in Europe that went way over budget? Too bad, now with the pandemic you don't earn money from gate receipts for quite sometime and the other events you want to host may take even longer.
I'm expecting them to finish in sixth place with two options then unfolding. If he wins a trophy (best case scenario: Europa League securing Champions League qualification) I'm expecting Mourinho to stay as he will no doubt point to that as a sign of progress very publicly. I expect this to then lead onto the classic third season Mourinho filled with sub-optimal performances, rants for not getting him the signings he asked for, a mid-table position around Christmas and his sacking.
In the second timeline, he has no trophy and Levy realises that the club has grown tired of his mentality, they fall out and he is sacked before pre-season. We then try to get a fresh, young and project-oriented manager in (dream would be Nagelsmann whose Bayern dream is not going to happen for a while given the impact of Flick).
No matter what happens though, I expect the club to operate with a reduced ambition of just making into European football while waiting for the stadium to pay itself off. While we don't have a Wenger who guarantees Champions League football despite the sale of key players and lack of funds, given the massive amounts in the TV deal these days and the revenue possible from the stadium I expect us to get back into serious contention sooner than later. The signings of Doherty, Hojbjerg and a potential 'backup' striker already point to this reduced ambition. Once the club is back on a much more financially secure footing, we might see a serious attempt at last from ENIC to establish the club firmly in the top four. Or else, we are sold to a prospective owner now that we have a big stadium and are worth more than a billion.
The only things breaking this cycle would be overachievement from our manager(s) with the limited resources and the key issue will be holding onto the talents at the club. Would someone like Lo Celso still want to play here when they could challenge for top honours in a bigger club?