Tottenham Hotspur are approaching a familiar crossroads. Ange Postecoglou has made a promising start in his ultimate aim of launching a sustained challenge for the game’s biggest prizes, reinvigorating the squad and reconnecting the club with its long-suffering fan base in a manner reminiscent of two predecessors.
Mauricio Pochettino was the last Tottenham manager to garner genuine affection from Spurs fans even after his sacking in November 2019 — so much so that many wanted him back in the summer before he ended up at Chelsea — but he left amid increasingly public frustration at the club’s failure to act boldly in the transfer market.
Pochettino walked the path previously taken by Harry Redknapp, Spurs’ manager from 2008 to 2012. Redknapp took Tottenham into the modern-day Champions League for the first time in its history in 2010-11 before threatening a Premier League title challenge in the following season, only for the club to opt against his preferred January signings that he believed would sustain their charge. Spurs were just five points off the leaders with 15 games left and Redknapp wanted to acquire forward Carlos Tevez and defender Gary Cahill. Tottenham chairman Daniel Levy opted for cheaper alternatives, bringing in Louis Saha and Ryan Nelsen on free transfers. Tottenham were unable to kick on and Redknapp left the club at the end of the season.
Postecoglou is still at a formative stage of his tenure but he has already packed a lot in — topping the Premier League table at the start of November before a run of four losses in five games. He will seek further backing next month to help close the gap, asking a question Levy has faced before: are Spurs prepared to be truly aggressive in the market in pursuit of glory?
The experiences of Pochettino and Redknapp are part of a cycle the latter believes Tottenham finally have to break, especially now the new state-of-the-art stadium and training-ground facilities are in place.
