No one is perfect and Levy has made his fair share of mistakes. But on the whole he has consistently moved us forward. One thing that people need to understand, however, is that the closer you get to the top, the more difficult it is to get to the next level. Getting from an average finish of 13th-14th to an average finish of 9th-10th is easier and takes less time than getting from an average finish of 9th-10th to 5th-6th, which in turn is easier and take less time than getting from an average finish of 5th-6th to 2nd-3rd. And when you are at or near the top you have more room to drop off than to go higher. The important thing is that you are always within that group of 3-4 teams that can challenge for titles. We were there for a spell and we dropped off (and I'll get to why below), but even to have established us as one of the top 5-6 clubs in the league and kept us there for the past 15 years with no money doping, is an achievement not to be scoffed at.
In my mind Levy made a couple of mistakes. First of all, he didn't put a cutting edge football operations structure in place sooner and take a step back from the football side of things. Had he done that around the same time Poch was appointed, we'd be in a different place right now. Secondly (and this is probably the result of the first mistake), he appointed Mourinho and Conte in the hope they would end the trophy curse, which was very reactionary and not strategic at all. The Mou and Conte appointments also set us back. A rebuild should have started in the 19/20 season and not the 23/24 season. But it is what it is and I can see why Mou and Conte were appointed: fans were clamoring for a trophy and trophy managers were appointed with the assumption by Levy that the playing personnel was at the required standards. I'm guessing the thinking was that we just got to a CL final the year before Mou was appointed, so it had to be good enough for at least a League Cup, no? Just needed the "winning" manager touch. With Conte it was the same and a huge investment was made, but he was totally the wrong manager to spend money for.
So here we are today. We ended up taking 2 steps backward to move 3 forward, but that's how it is in many walks of life and business. What's important is that we are constantly inching forward and we are. Maybe not at the speed that some would like, but in today's football environment and with the financial regulations in place and yet to come giant leaps are no longer possible. We are, however, extremely well positioned to take advantage of the new football financial landscape thanks to ENIC. If someone had told us 5-10 years ago that we would be able to outspend clubs like Barcelona, we'd be laughing. Yet here we are and with Ange we've only just begun to put our stamp on the football side of things too.
I think you always have to look at context with Levy
- In my opinion, his vision for the club is years ahead of everyone else
- He understood very early we need better revenues (stadium), non football events, etc. than most (City is copying by building a non football facility, Real Madrid basically copied the two pitch idea), not his fault London & Government fudged us around for years, so stadium probably got built 5 years later than it should have.
- He was the first (or one of) to have a DoF in England, I remember Sky/BT/BBC constantly harping on how "Levy doesn't understand, DoF's a European thing and won't work in England where SAF/Wenger types are the model" fast forward a decade? remember his early DoF got poached. The football structure got delayed because of Poch (who wanted more power and complained about being "coach")
- He tried to revive the club when Chelsea then City came about, so two top spots were instantly taken.
The result
- Levy's legacy is a "future proofed" Spurs, we are safe from the worries of an Everton, West Ham or even Villa. The stadium will always generate enough money to buy our way out of bad decisions (much like Liverpool and United have done over last decade), that plus training ground means infrastructure cost outlay is a minimum over next decade or two. The brand is also at an all time high globally.
- We are (this is often forgotten in the trophy conversation) in the most consistent run of results in the league in the clubs history, we have played in Europe in 16 out of last 17 seasons (club has not played in Europe more times in his history vs. under ENIC/Levy)
The fudgeups
- Jose/Conte, in my opinion this was always an attempt to get something out of the squad Poch failed with, one last chance with a proven winner and perhaps with stadium revenue not available previously to support (then Covid hit).
- The times when we went away from our good recruitment (era after Son buy -> Paratici coming in)
I'll answer OP question separately