You would have to give me an example of a time where, with ENIC/Levy in charge, they had pushed their chips in.
To me Tottenham Hotspur were the club that had won the FA Cup more than any other. We had Englands best 2 players in Gazza & Lineker. We were managed by Barcelonas former coach Venables. We were a special club. Being the 6th best team is not the standard we strive for. This is the standard and it always will be.
So to answer your questions/points
1. They never have, this is both the curse and amazing work of Levy. The owners (not Levy) gave him a football club that was in a dire situation, that had a decade of misery behind it, was behind clubs we would no longer consider rivals and gave him a mandate of run the club has a self-sustained financial entity, Levy took a look around and realized two things, firstly we were at a massive disadvantage to the clubs that managed to be top 4 in the early years of PL/CL that gave them a massive financial springboard to create a gap, second Leeds had just imploded to trying to play with said big boys and by taking risk betting on future results.
His response, build the financial side of the club to allow us to compete (clubs like Villa, Everton, West Ham, Sunderland, Leicester will never consistently compete because they make ~250M/yr less than top 6, over 5 years that is a gap in the billion+ range, no owner input is going to cover that), with the logic that on field success will follow with the additional revenue being available (that owners would not provide)
The result, the most successful upgrade of a club infrastructurally and financially probably ever seen by legitimate means, and the most successful consistent league run in the clubs history, and yes, we can say 2 trophies was not good enough, but chances were there for more and see second point. Because of the financial restrictions, Levy tended to use his risk calls to counter when we were in trouble vs. when we push the boat out.
2. Your version of Spurs (80's) was one of the clubs that had a financial advantage (we had a better chunk of tv deal than the Sky model that came later), your version of Spurs didn't have RA's Chelsea, or UAE's City or Saudi's Saudi Sportswashing Machine to compete with either. If we had competent football authorities those clubs would not have happened and Spurs would absolutely have won more in the Levy era.
None of this says we shouldn't want more, but part of my huge frustration of the time between your Spurs and now is
- The media has manipulated fans (Sportswashing works) into this idea that City/Chelsea are some great achievement and not a stain on both the football and moral landscape, and the people involved with them are just geniuses
- This has led to Spurs being criticised (small club, look how they delighted in the Ange interview) for not being able to match an oil state in spend/wages
- Our own fans (see this board every day), equating ambition with how much money beyond your revenue stream you can throw at players
I think Levy had two primary flaws, one understandable, i.e. the decision to not push the boat out for more success due to risk concerns, the other I believe his initial goal was to get us top 4 and when he got us there, didn't quite grasp how to push on (partially a funding issue which is why I think in last couple of years he was looking for investors)
