Martin Jol took Spurs to the brink of Champions League qualification while constantly running on a rug-pulling treadmill of his best players being continually sold from under him.
Mauricio Pochettino somehow marshalled a shallow squad to regular Top 4 finishes and an EPL Runners-Up position, despite a lack of ongoing investment. He wanted the likes of Zaha and Grealish, along with a back-up striker of some sort, but was instead fed on the gruel of Njie and Nkoudou, leading to a kind of Stockholm syndrome, where the manager (a job-title he suggested ought to be changed due to his lack of control over transfers) was made to feel grateful for the likes of Moussa Sissoko.
Harry Redknapp took Tottenham into what appeared to be a three-way title race in December 2011 and requested that Daniel sign Carlos Tevez and Gary Cahill in January simply to allow the club to push on. He was instead forced to make-do-and-mend with Louis Saha and Ryan Nelsen, and the title challenge inevitably wilted away to nothingness.
This psychological abuse of the manager culminated in a form of football gaslighting when Tottenham’s becoming the first club in Europe’s top five leagues to sign no players in two consecutive transfer windows was disingenuously attributed to the manager not wanting to sign the players offered to him. In spite of this failure to strengthen at all, even when the club had more players taking part in the last four of the 2018 World Cup than any other club in world football, Pochettino somehow dragged Tottenham to a Champions League final where he was forced to play a still-injured Harry Kane due to a lack of viable options. That summer, however, all the talk of Paulo Dybala proved to be just that, and Tottenham once more entered the next season without cover for Kane, a decision which ultimately cost them, dear.
And, most recently, though comparatively a mere fleeting cameo in the Daniel Levy Show, during Jose Mourinho’s stint in the not-so-hot-seat he managed to push the club at one stage to first place in the Premier League in spite of itself, and later to a cup final, but was nevertheless also thwarted by the club’s unfit-for-purpose transfer policy and directorial micro-management. He was handed players he would not have chosen, prevented from shipping out some of the deadwood that still infects the squad today with the toxic stench of apathy, and his stated goal of improving the defence was hugely undermined with the only centre back addition being another of Tottenham’s perennial ‘ones for the future’ in the form of Joe Rodon (who I am sure will ultimately turn out to be a very astute buy, but… well,… let’s just say there’s a recurring theme of ‘jam tomorrow’ where Daniel is concerned).
There’s been no more success with Directors of Football than there was with managers. Frank Arnesen quickly realised he’d be better supported at Chelsea and headed for the hills. Damien Comolli was uninspiring but undermined. And when Paul Mitchell dared to challenge Daniel’s world-view and his coterie of yes-men, he was shown short shrift and placed on gardening leave that lasted for only slightly less time than the second ice age.