For most of his time as Tottenham chairman, Daniel Levy oversaw real and undeniable growth.
Spurs were mid-table when ENIC took control of the club in 2001. Since then, they have elevated the club to consistent European contenders (despite a lack of trophies) and have invested in state-of-the-art facilities.
But when they saw that the time had come to go from almost men to winners, they pushed the club back again. And again. And again.
These are the biggest mistakes by Levy and the Spurs board since they reached the UEFA Champions League final in 2019.
1. Too little, too late in the transfer market
This is a bit of a prelude to this whole debacle, but it’s still true.
From 2018 to 2019, Tottenham spent almost 18 months without signing. Not one. Nothing. Nothing. The board lamented that making transfers was difficult.
Spurs spent the 2018/19 season running on smoke. Mauricio Pochettino’s magic saw the club reach its first Champions League final in spectacular fashion, but a rebuild was clearly needed.
Tottenham signed two new star players in Tanguy Ndombele and Giovani Lo Celso, both of whom proved very disappointing, while the additions of youngsters Ryan Sessegnon and Jack Clarke did little to help the immediate cause.
2. Replacement of Mauricio Pochettino by José Mourinho
Firing Pochettino was totally understandable. The results were bad, not horrible, but bad nonetheless. The team seemed exhausted and out of ideas.
What was not understandable was that Levy, recorded in the club’s Amazon Prime documentary, would claim that 2019 José Mourinho was “one of the two best managers in the world”.
The president clearly thought the team was closer to competing for top honors than it really was.
3. Fire club staff during lockdown
A football club that would sell for billions if put on the market furloughing ordinary club staff during an unprecedented global pandemic was a horrendous sight. It was only saved and downplayed in hindsight by a quick reversal, but this would not be the only deaf action taken by Levy and company.
4. The Super League debacle
Many people claim that Levy did not support Mourinho, but Spurs’ 2020 summer window was considered pretty good at the time, they were even named our transfer window winners.
Tottenham were on a high in December, though they quickly fell off a cliff for the rest of the winter. Levy can’t take too much blame for that.
But while Spurs were in decline, they secretly signed up for the European Super League. Fan protests saw them pull out a couple of days later.
5. Fire José Mourinho a week before a cup final
Levy really dropped the ball with his timing and the ruthlessness of his managerial changes. He used to be famous for pulling the trigger too fast, but since then he’s dawdled when he needed to be fierce.
His decision to sack Mourinho would have gone down a little better had it happened in February or March, but not a week before facing Pep Guardiola’s Manchester City in the Carabao Cup final.
6. Trust Fabio Paratici
The good news for the Spurs was that Levy was realizing his mistake and wanted to hand over control of football operations to an experienced professional.
The bad news was that Fabio Paratici received the keys to the club after leaving Juventus under a cloud of moral and legal uncertainty.
Still, what’s the worst that could happen?
7. Having to go back on Gennaro Gattuso…
Levy declared in May 2021 that the club had lost sight of key priorities and that their next manager needed to foster a style in ‘Spurs DNA’.
This was an immediate mismatch with Paratici, who was looking for a more defensive coach. He wanted to name the horribly incompetent Gennaro Gattuso, only to have fans protest against such a move due to previous racist, sexist, and homophobic comments.
The club suspended negotiations.
8. …and deciding on Nuno Espirito Santo
The ultra-conservative Nuno left Wolves at the end of the 2020/21 season and was heavily linked to jobs at Everton and Crystal Palace, only to be passed over.
Somehow he landed on his feet at Tottenham. Two plus two equals five.
9. Trusting Fabio Paratici 2: Electric Boogaloo
The fears of the Tottenham board came true when it was confirmed in November 2022 that Paratici would be charged as part of an investigation against Juventus and its financial mismanagement in recent years.
Juve’s entire board of directors resigned, but Spurs kept their heads in the sand hoping the problem would just go away, perplexingly keeping Paratici to the bitter end.
He finally left his position at the end of April when his global soccer ban was upheld. Considering that Spurs were still relying on their judgment on a new manager until his resignation, this turned out to be a costly decision.
10. Not acting before with Antonio Conte
Tottenham should have left Conte behind when all signs were going down and it became clear over the winter that he would not compromise his future.
They would have had plenty of time to find and interview suitable replacements, but instead found themselves in a bizarre situation that culminated in the Italian losing his mind and lashing out at players and owners in a press conference.
11. WHY IS CRISTIAN STELLINI IN CHARGE?
What is the best way to get rid of the lingering stench left behind by Conte?
Promote your loyal long-term assistant. Genius!
12. The deaf talk of Cambridge Union
With Tottenham stumbling from one disaster to the next, Levy needed to prove his doubters wrong and show that he had a plan to fix the club’s various problems.
Talking at the Cambridge Union for nearly an hour in a slightly self-indulgent manner was not the way to go.
13. Firing interim manager for another interim manager
Sunday’s 6-1 implosion at Newcastle was the result of four years of neglect at board level.
Stellini was not qualified to be a head coach, and his association with the unpopular Conte left an unbalanced dressing room, lacking in drive and energy.
It was a failure on all levels.
To their (very, very, VERY) minimal credit, the first team issued a refund to supporters who attended the match. Just because of a computer glitch that strips those fans of loyalty points in the process, which is a simple bug but horrible for optics.
14. Allow Mauricio Pochettino to join Chelsea
Should Pochettino have been a leading candidate to replace Conte? Not necessarily, but at least he should have been in the race. He wasn’t, partly due to Paratici’s supervision.
The Argentine would have been interested in a return to north London, and even at the end of talks with Chelsea would have recently responded to any calls from Spurs. That ship has sailed. (90 minutes)
The fans shouldn’t be able to dictate who the coach is, but the chants to Pochettino in recent home games left a clear message: the board should have admitted their mistake. And now Tottenham’s best manager in a generation has a clear path to join his rivals.
15. Neither the men’s team nor the women’s team have a coach, what the hell is going on?
None of the senior teams have a coach.
The men’s team is finally falling deservedly down the Premier League table.
The women’s side remains in danger of relegation, with the Daily Mail reporting that Levy wants to shut down the WSL.
It seems impossible for things to get worse, but can the club be trusted not to make such an effort?
