That was a fair call at the time.
1. Poch was okay with the idea of signing Grealish but didn't especially want him. So no surprise that Levy wasn't prepared to go balls deep.
2. No other club was in for him at the time at that price.
3. Grealish had just had a great season in the Championship but was largely unproven at PL level.
4. Given all of which, Spurs' bid of £20m was a lot at the time.
5. And Spurs did eventually agree a deal with Villa at £20m. But it was called off a day or two later when Villa were taken over.
As to this transfer window, it has indeed been a bit of a shambles thus far. But not because Levy is being tight. It's because both Traore and Luiz preferred other clubs. Entirely understandable in both cases. But, yes, very disappointing - especially missing out on Luiz.
Spurs are supposedly still expecting three in and quite a few out over the next couple of days. Mostly loans. I'm not especially enamoured by the names being linked - a number of Juve squad players. A tad underwhelming.