Since City were catapulted into the financial elite in 2008, they have finished above Spurs in nine of 13 seasons and, in three of those campaigns, effectively denied them Champions League football by being above the fifth-placed north London club.
Without a financially-boosted City, Spurs might well have finished in the top four in nine of the previous 13 seasons and quite possibly won a trophy or several.
Levy’s careful business plan would be far more celebrated today and the perception of Spurs and their embattled chairman would surely be very different.
The question feels relevant because yesterday’s opponents are the next club hoping to quickly leapfrog Spurs following their takeover by a consortium backed by Saudi Arabia’s Public Investment Fund.
Even before considering the ethical questions of Saudi’s human rights record, you can understand why Levy would feel particularly aggrieved at another monied Premier League project.
Nuno Espirito Santo’s side burst Newcastle’s Saudi bubble with a 3-2 win at St James’ Park which underlined the scale of the task facing the Toon’s new owners, but as much as any club in the Premier League, Spurs stand to lose out from the changing of the guard on Tyneside.
Levy’s brand of fiscal prudence is now up against three projects backed by fabulous wealth, also including Roman Abramovich’s Chelsea, as well as commercial behemoths in Manchester United and Liverpool. Spurs have their own trump card in their stadium, which successfully hosted the NFL yesterday, but competing at the top will be no easier if Newcastle’s hopes are realised.
Spurs comfortably bested Steve Bruce’s struggling side on an occasion when the football felt secondary following the collapse of a supporter, which held up play for 20 minutes.
The visitors responded to Callum Wilson’s second-minute header with three goals before the interval through Tanguy Ndombele, Harry Kane — his first in the League this season — and Heung-min Son to offer optimism about their own futures under Nuno.
Kane looked back to his old self, giving Spurs the lead with an expert arcing run and deft first-time flick, while Ndombele looked the part at No10. A late own-goal by Eric Dier after Newcastle substitute Jonjo Shelvey was sent off was more than the hosts deserved.
The win was another small step forward for Nuno’s side, but Newcastle have taken a giant leap this month and, in the longer term, Levy and managing director Fabio Paratici must consider how best to be competitive in a division boasting another club who can consistently outspend Spurs.
One approach is for Spurs to simply accept that they cannot compete in the same ways as their wealthier rivals and return to a business model for growth. As they have progressed, Spurs have arguably begun to behave like a richer club than they are, evidenced by their refusal to sell important players and by spending big on individuals.
The question of whether they should have been more open to offers for Kane in the summer is complicated, but Spurs could have sold Dele Alli, Dier and Danny Rose when they had the chance, and cashed in on Toby Alderweireld, Christian Eriksen and Mousa Dembele sooner.
Borussia Dortmund and Leicester have remained competitive by selling star players for huge sums at the right times, but Spurs have become reluctant to accept that selling is not necessarily an admission of weakness, but rather a prudent way of raising funds to refresh the squad.
Of course, there is no use in selling players if they are not effectively replaced, and Spurs’s recent recruitment policy has also felt misguided. They have taken huge financial risks by agreeing to spend more than £50million on Ndombele, Giovani Lo Celso and Cristian Romero.
While clubs backed by big money can afford to quickly replace expensive disappointments, Spurs cannot. Most of their biggest successes in the transfer market have been young, affordable, high-potential players such as Gareth Bale, Dele and Kyle Walker, while almost all of their 10 most expensive transfers have underwhelmed.
As Spurs begin another rebuild, showing a willingness to sell and taking a less risky approach to buying could be part of their strategy to compete.
It bears repeating how much more successful Spurs would probably have been if other clubs had not been revolutionised by investment, and over the next decade you wonder if Newcastle’s windfall could impact their fortunes as much as City’s change in ownership.
The Magpies will surely pose greater threats to Spurs in future than they managed yesterday and it is up to the Londoners to be smart in order to be successful again.