Levy has made a few missteps over the past 3 years, and I think they are inter-related. First, and most important, he had the club be the general contractor for the stadium project, thus retaining all the risk of screw-ups. It would be most usual for such a project to enter into a contract that transfers more of that risk to a professional. Thus, the cost overruns impinged on club cash-flow (but NOT FFP limits, as I understand stadium matters are outside FFP). That probably affected the net spend in the 2 years prior to this summer.
Second, he kept certain players who were popular (with both Poch and the fans) rather than sell and replace, and this was a function of the cash flow to a large degree. Think Toby, Jan, Danny, Christian, Wanyama. I'm new to footie, so I'm learning about contract structures, transfer markets, etc, which are quite different from the US sports I grew up with. Spurs performance last year may have even been enhanced by a lack of transfers, a settled and happy squad. A healthy and fully-bedded in Lucas helped.
Third, I think he failed to anticipate the recent behavior of many players in their last 12-18 months to strike a more defiant attitude towards extensions or sales, settling to run out contracts and take advantage of teams such as Juve offering big wages and sign-on fees to players they can acquire w/o a transfer fee. I think now that a team should resolve a player's future with at least 2 years to go in the contract, lest it become cornered.
Fourth, and related, allowing the Eriksen cancer to fester was a major mistake. He wanted out, so out he goes. Quickly. CE also apparently had some surgery this summer, but it's never been fully reported. Did that affect the ability to sell him?
Finally, this summer Levy tried his usual tactic of squeezing every deal for the last drop of juice, and that really hurt. He should have bitten the bullet and sold several early on and acquired Lo Celso/Fernandes/Olmo/Dybala (2 of the 4? 3?) early on too, so they could get acquainted with Poch and the rest of the team and be fully fit and running with the team. The last-minute additions have negatively affected the performance in this first 30% of the season.
This summer with the stadium essentially completed Levy did back Poch in the transfer market. Ndombele is likely to be as good as expected. The only drawback is that his fitness when he finally reported was not up to Poch's standards, apparently. He shows every sign of progress, understanding what is expected and intending to get there.
Clarke, a young acquisition for the future, has been unproductive. Hopefully, the 2d half will see his situation sorted, either playing at Leeds or re-loaned elsewhere. As I understand it Poch had faith in Bielsa at Leeds. Oh, well. Either way, Clarke was not going to be the solution to this season.
Lo Celso may be as good as hoped, we just don't know yet. But the delay in getting his deal done, plus his summer playing elsewhere that affected his integration with the team, was due to Levy IMO. The injury at the first international break was just added burden.
Sessegnon was known to be injured, but he has been a team target for a while if the press has any accuracy, and that would have to be Poch IMO. His setback was a problem, but he's now looking to get more fully involved. That looks to pretty seamlessly solve the left-back problem of Rose, but the overlap period has not gone to plan.
Selling Trippier looks premature, but certainly the injuries to KWP and Foyth made that more apparent. Selling Aurier would have been better IMO, but Trippier's age may have colored the evaluation.
The question for this year is getting those with knocks back fully fit. I think KWP and Foyth can hold down right-back adequately. Getting the youngster Tanganga some first-team time (and a contract extension) would be helpful in the middle defense, too. Getting Parrot some time up front would be good. Getting Lamela healthy would help - he was playing well. But his frailty over the years has to be recognized, and he should be sold. That may be tough for Poch to do to his countryman, but it is just reality. I really like Lucas, and hope he gets more opportunity.
They need at least 1 midfielder in January, maybe 2 if the opportunity presents. A quality right back would help, but as I said above I think that hole can be plugged adequately internally, and then re-evaluate in the summer. Should Foyth play on the right or in the center? IDK - in Poch I trust.
Finally, Levy refinanced the stadium construction debt in a really low cost and long term deal. He still hasn't sold the naming rights, so that can add to the transfer kitty, and it will be substantial. As I understand FFP, and the team's cash flow based on their public accounts, I estimate that Spurs will have ~£80-100mm per year to spend on transfers as long as they qualify for the UCL KO stage and don't allow their wage bill to inflate too much.
The last two years of standing still have caught up with them. It's fixable, but it will take some time to get it right. Below is the question posed in a slightly different way by others earlier today.