After a comedic, shambolic, all-too Spursy search for a permanent manager finally settled on one Ante Postecoglou, it seems like the club from the town that London eventually added as a suburb might have their man. After all, Postecoglou is fresh off of winning a domestic treble with Celtic, plays attacking football, and sees Tottenham as a step up rather than a step down. What could go wrong? For one, Kane staying. More on that in a moment.

Let’s be clear from the off here. This looks like a smart appointment, smarter maybe than some of the other managers Tottenham pursued. He’s a good manager even if his CV is a little thin. He may not be as glamorous as some of those other managers, but he’s willing and maybe even eager to be here, and that’s a far cry from Conte or Mourinho. HIs belief in positive, attacking football also sets him apart from Nuno.

And yet.

Much will be made of that domestic treble. Three trophies in one season? That’s more than Tottenham have won in the last twenty years combined (I can’t do the maths to be more precise). However, Celtic have won the Scottish Premiership nine of the last ten seasons, the Scottish Cup five of the last seven, and the Scottish League Cup six of the last seven. In other words, while a treble is nothing to scoff at, it’s worth pointing out how much Celtic and Rangers dominate the SPL. Hell, even Steven Gerrard guided Rangers to league title, and we saw how well when he tried to ply his trade at Aston Villa.

Costeglou has a massive task to undertake. The squad desperately needs an overhaul, and Daniel Levy is infamously tight-fisted. Costeglou has apparently already been told that he’ll have to work within his means. Then again, he did rebuild a Celtic side that finished 25 points behind Rangers. Then again, rebuilding might be a bit easier for a league behemoth like Celtic than it is for an aspiring club like Tottenham.

That brings us to Harry Kane. He’s arguably the club’s best-ever player and he’s probably two or three seasons away from surpassing Alan Shearer as the Prem’s all-time goal-scorer. He’s also 29, hardly ancient, and his chance at winning silverware is growing narrower by the day, and it’s made narrower by the idea that Postecoglou won’t be backed aggressively (if Conte and Mourinho weren’t backed, it’s hard to imagine Postecoglou being treated any differently). To fund the overhaul that this squad needs in the face of Levy’s refusal to spend, they may have to sell him to a club like Real Madrid. Levy is right to resist selling to another Prem side (not that we know anything about the sting of selling a talismanic goal-scorer to a domestic rival).

Selling Kane to Real Madrid for, say, £120m might be enough to allow Levy to bring in two or three quality players just on that revenue alone. Of course, he’ll need a replacement for Kane unless Son or Richarlison can fill his boots (I’ll give you a minute to wipe your spit-take from your screen). He’ll need a keeper. Others, like Højbjerg, Dier, Davies, and Perisic, could do with an upgrade. That’s five off the top of my head. Moura’s also gone. There are some good young players in there, but Postecoglou faces a daunting task. If Kane stays, Postecoglou is yoked to him and will have no choice but to tailor his tactics to a slow but clinical player who can’t press and to whom others will defer. Would Kane accept a reduced role that sees him as a second striker who drops deep so that Son, Richarlison, and Kulusevksi run in behind onto balls he lays off for them?

That’s his Scylla and Charybdis. He can pursue Shearer’s record, or he can pursue silverware. Threading that needle would be an incredible balancing act (if you’ll permit a mixing of metaphors, idioms, and allusions). If there’s a manager who can help Kane navigate those treacherous waters, it may in fact be Postecoglou.

Having said all of this, it still feels like Tottenham are a season away from challenging for a top-four spot or domestic silverware. Without European entanglements, Postecoglou will have more training time to reshape the squad and its culture, but a lot of unanswerable questions loom over the club’s future. The sooner they resolve Kane’s situation and that situation’s repercussions, the sooner they’ll find their way back to relevance.