Tottenham stand at a crossroads. But then they always do. They have been standing at a crossroads for at least 50 years. And while some roads lead through cup finals and hopeful vistas and others through gloom and Tim Sherwood this, perhaps, is the true history of the Tottenham: life as a series of crossroads that lead always, eventually, back to another crossroads somewhere in the Valley of Not-Quite-There. Often Tottenham seem to take the right road. In the final week of 2009-10, for instance, they went to Manchester City needing to win to take fourth from Sheikh Mansour’s rising side and claim their place in the Champions League. This felt critical, a chance for the victors to take a decisive step, to claim the financial rewards of Champions League football and use that to consolidate their advantage. Peter Crouch headed the winner for Spurs eight minutes from time. Tottenham enjoyed their European run – Gareth Bale destroying Maicon, Crouch’s winner against Milan, Joe Jordan squaring up to Gennaro Gattuso; since then City have won the Premier League six times. The reputation for Spursiness, their capacity to falter at key moments, is not unearned, but Tottenham do win quite a lot of these decisive games. They did it last season against Arsenal, but it is Arsenal who are challenging for the title. Sunday’s match at St James’ Park is another crossroads. Despite everything, victory would lift Spurs level with Newcastle, albeit having played a game more. Nobody expects them to win and the sense must be that even if they do, even if they can qualify for the Champions League with all the advantages that entails for squad-building, in terms of revenue and attracting talent, it may ultimately be as meaningless as that win at the Etihad Stadium 13 years ago. With the power of a state behind them, Newcastle should be able to accelerate away from Tottenham just as surely as City did. Which is where Daniel Levy is due sympathy. City and Newcastle have spent astutely. There has been little waste. But the great advantage in effect limitless wealth offers is that clubs can afford to make mistakes. A season outside the Champions League does not have a devastating impact on spending. Levy has done the best thing a non-state-backed club can do, which is to build probably the best club stadium in the country, a solid generator of revenue (unless there’s a pandemic, the timing of which was highly unfortunate for Tottenham). It is an indication of the shifting patterns of wealth that the five English clubs providing stadiums for the Euro 2028 bid are City, Spurs, Newcastle, Aston Villa and Everton, a group that would take some explaining to a visitor from 20 years ago – and in Everton’s case, may take some explaining in 2028. But financing the stadium meant trimming budgets elsewhere and that, as much as anything else, was what checked Spurs’ rise under Mauricio Pochettino by making it impossible to refresh the squad as he would have liked. In other respects, Levy has been at fault – recently in his dithering in the whole Fabio Paratici shambles. Spurs need to win six of their final seven games to match last season’s points tally. Perhaps Levy would argue things are not quite as bad as they feel: three wins would match 2020-21; two wins the season before that. It’s just that when you’re playing in arguably the best stadium in the country, employed Antonio Conte and then spent £157m last summer, producing the second-best season since 2019 doesn’t feel much like progress. Spurs have lost their sense of who they are as a club, as though the grandeur of the stadium has made Levy feel they need a big-name manager as a shortcut into the elite. That is why Julian Nagelsmann and Luis Enrique are among the preferred candidates. Perhaps either would be successful. Both still have something to prove, Nagelsmann having lost his dream job at the age of 35 and Luis Enrique, despite lifting the Champions League with Barcelona, having never entirely convinced at club level before producing an attractive but ultimately toothless Spain. But Tottenham’s recent experience of big names is not good. José Mourinho and Conte gave the impression they were doing Spurs a favour by being there. So when things went awry it was the club to blame for letting them down rather than the other way round (which may not be entirely unreasonable: Spurs are the only club where Mourinho has failed to win a trophy since he left União Leiria in 2002; Conte since he left Siena in 2011). What Spurs need is somebody in the mould of Pochettino as he was in 2014, an ambitious manager on the up with the charisma to pierce the gloom. Which may still be Pochettino, whose career since leaving Spurs in November 2019 comprises a desultory 18 months as manager of Paris Saint-Germain. But identifying that up-and-coming manager is difficult – and given recent appointments and signings, it is not clear there is anybody at Tottenham with the requisite vision. It’s easier, always, to go for proven quality, to assume that success at a previous club will necessarily be replicated at Spurs, when the cases of Mourinho and Conte show that not to be true. That is where the lack of a guiding philosophy has hurt Spurs. They have become accustomed to adjusting their style to the manager, rather than selecting a manager to fit the ethos that underlies everything at the club from academy to recruitment. It is inevitable the style will change again with the new manager. But most of all there needs to be a longer-term vision and in that sense the new sporting director in the wake of Paratici’s resignation on Friday may be the more important appointment. Set the principles and pick the manager rather than chasing always after the latest personality. Set the satnav rather than taking a guess at every junction. But when you’re taking on state-backed clubs, every route is going to be steeply uphill.