On the eve of the Champions League final, Pochettino confirmed he would stand down as manager if Spurs were victorious, believing his work to be complete. In truth, admission of this was the ultimate signal that he was flagging and on the way out sooner or later. There was uproar when he was sacked a few months later, but there was at least enough reason behind that decision. Tottenham started 2019-20 poorly and weren’t playing with anywhere near the same trademark intensity of previous seasons. What didn’t make sense was Levy’s sudden pivot in strategy.
Believing the squad to be closer to winning the most important of trophies than they actually were – despite making only four signings over the last two years and the team still visibly exhausted – Levy completed a long-held ambition of hiring Jose Mourinho, claiming the declining ex-Chelsea and Manchester United boss was at that point ‘one of the two best managers in the world’, even when it was clear to the rest of the world this was no longer the case.
Tactical reservations over Mourinho aside, the ‘Special One’ was also used to working with massive budgets that dwarfed the competition. Tottenham, despite the stadium move, couldn’t quite promise the same yet. In his sole summer transfer window as head coach, Spurs signed Matt Doherty, Pierre-Emile Hojbjerg, Sergio Reguilon, Joe Rodon and Joe Hart. Bale also returned on a season-long loan, though judging by how infrequently he played under Mourinho, is regarded in hindsight as a Levy-led signing. After leading the table early in 2020-21, the Portuguese was sacked in April of that season with the team in seventh and only six days from playing in the Carabao Cup final.
Mourinho’s failure was entirely predictable, yet the club did not learn from their mistakes. They were forced to settle on Nuno Espirito Santo as his replacement after over two months of trying to find a successor, only to sack him after 17 games when their top target, Antonio Conte, was open to working again.
Though Conte is often put in the same bracket as Mourinho by Spurs fans, he did enjoy initial success, leading the team to an unlikely top-four finish at the expense of Arsenal. Heading into the summer of 2022-23, it was Tottenham who were expected to become title challengers, not their north London rivals.
Alas, it was a familiar story. Spurs bought poorly, didn’t add enough quality to surround Kane and Son, and towards the end of a testing season which also saw several tragedies in his personal life, Conte effectively quit by targeting all corners of the club in an explosive press conference. That summer, Kane was sold to Bayern Munich after refusing to sign a new contract, and you could hardly blame him.