Every few years, the Premier League throws up a team of loveable losers, winning plaudits for their style, their principles and their refreshing capacity to punch above their weight; O'Leary's Leeds, Keegan's Newcastle and even Rodgers' Liverpool briefly, all aroused admiration from the general football public, but ultimately failed to capitalise on the opportunity to establish a dynasty, and soon returned to relative mediocrity. Common factor in their downfall? An inability (or reluctance) to win a domestic cup competition to begin the winning cycle.
Enter Pocchettino, and his dismissive approach to the FA and League cups; in a squad collectively scarce on relevant winners medals, and at a club with practically no recent culture of winning, it's moronic of him to ignore the importance of putting something in the cabinet to forge that so-far elusive mentality.
For all of the vindicated admiration for the work the manager is doing with relatively limited resources and his development of young talent, he has to stop bottling it when it really matters: losing every big domestic head-to-head this season, and even going back to the best opportunity the club had to win the league in half a century in 2016, collapsing when going toe to toe with a bunch of championship players led by a Tinkerman.
He has some great players available to him, arguably the best in the league in practically every position - he can't hide behind rival investment forever, especially when he's had a stronger squad than the previous two league winners.
Not a popular view, but I feel it's time for Levy to evaluate whether Pocchettino is the right man to lead the club into the next phase of its development: the club now has the infrastructure to succeed, not just relatively but literally. The inability to find a win when it really matters in the recent past suggests he probably isn't.
This squad, with a proven winner coaching it, could do what those aforementioned clubs couldn't and establish a sustained, successful presence at the very top of English football. The way things are going at the minute, there's no guarantee of Champions League football going into the new stadium, especially if Pocchettino can't find a way to stop losing 6 pointers. Now the likes of Kane, Eriksen and Alli have experienced and excelled in Europe's elite environment, I doubt they'll be happy to be exiled from it, especially when the domestic and continental rivals who perpetually participate in it pay better wages.
Personally, I'm a bit of a Pocchettino fanboy for his contribution to the development of young British talent, but this club now both deserves and requires more than a glorified youth coach.
If Mourinho is bored of living in a Salford hotel, I'd bring him back to London. He'd inherit a squad ready to win, and a superior one to the United one he's currently in charge of. Being the man to finally bring success to a club previously starved of it would appeal to his ego too. Beyond him, Rafa Benitez has won with less talent at his disposal in a number of different environments - he's a cup specialist who, even if he didn't win the league, would help cultivate a winning culture to pass on to a longer term successor.
Rose and Walker got bored of working under Pocchettino, but that's relatively irrelevant: if Kane, the Dane, Toby, Vertonghen and Alli develop the same frustrations, Levy has a problem, because all would walk into 99% of winning teams in Europe, and be paid better for it too. They need to be stimulated by success, and I suspect Pocchettino has taken them and the club as far as he can now.