Daniel Levy’s excessive caution and stubbornness meant he could never lead Tottenham to true success – now he’s gone they can finally make giant leap, writes OLIVER HOLT

Daniel Levy built the foundations of the modern Spurs. He put everything in place to turn them into a monolith of the modern game: one of the best stadiums in Europe, a state-of-the-art training ground and a succession of elite managers.

Then on Thursday evening, when no one was expecting it, the Spurs executive chairman removed the last remaining obstacle to the pursuit of the big trophies that Tottenham^[1] supporters crave: himself.

When Levy resigned after nearly 25 years at the helm in north London, it was a sign of the impact he has had on the English game in the first quarter of the 21st century that the announcement should be met with the same sense of gravitas that has greeted the departures of other great architects of club progress.

Levy may never have quite enjoyed the popularity of iconic figures such as Sir Alex Ferguson^[2] and Arsene Wenger^[3] but if those managers were always the dominant personalities at their clubs, it was always Levy who was the main man at White Hart Lane. His personality defined the club. It was a constant.

Levy’s greatest legacy will be the stadium that he built. Only the revamped Estadio Bernabeu in Madrid exceeds it in its grandeur and its stature. 

The Red Bull Arena in Leipzig beats it for invention but the Tottenham Hotspur Stadium is the best modern arena in the country by a distance.

After 24 years, Daniel Levy has resigned as Tottenham’s chairman in a stunning move

Levy built the stadium and he transformed the team that played in it from the also-rans that performed at White Hart Lane

He built the stadium and he transformed the team that played in it from the also-rans that performed at White Hart Lane in the years before he took over in 2001 into a side that consistently qualified for European competition.

Yes, Tottenham’s Europa League success in May, achieved with victory over Manchester United in the final in Bilbao, was the club’s first trophy since 2008 and only the second since Levy took charge but Spurs have a claim to be better run and in better financial health than any other team in the top flight.

Levy ran the club responsibly and well. Its wages-to-revenue ratio is lower than all its main rivals and the move to the new ground has transformed its matchday revenues which has put it in a good position to cope with the demands of PSR. 

Twenty-five years ago, the idea that Spurs were genuine members of England’s Big Six was fanciful. Not any more, despite last season’s desperate 17th place finish.

But there is a significant caveat to all this. Levy may have built a magnificent stadium but there have been no major honours to put in its trophy cabinet. 

Under his leadership, when it came to the Premier League and the Champions League, the cupboard was bare.

There were near misses, particularly the defeat to Liverpool in the 2019 Champions League final in Madrid, the third-place Premier League finish to Leicester City in 2015-16 and the hope and flair of the first half of the 2011-12 campaign when they were well-placed at Christmas only to fall away in the second half of the season.

There is a reason why Levy also excited so much opposition among the club’s support, too, opposition that has seen demonstrations against the board in recent years and the club’s progress on the pitch being outstripped again by local rivals Arsenal.

Levy took the club so far but he seemed either unwilling or unable to push it up the final step to the summit. There were times when it felt that excessive financial caution outstripped Tottenham’s ambition.

There is a reason why Levy also excited so much opposition among the club’s support

Tottenham achieved Europa League success in May by defeating with victory over Manchester United in the final in Bilbao

Vinai Venkatesham (left), who was a senior Arsenal executive for six years, will now have major power at Tottenham 

Sometimes it was caution. Sometimes, it was just Levy’s love of the deal and, specifically, Levy’s love of getting the better of an opponent in a deal. He almost always achieved that but it was often a pyrrhic victory.

He dismissed 15 managers in his time as chairman, which is a damning indictment both of his ability to pick the right candidate and his ability to work with that candidate but it was that love of the deal that damned him most.

Time and again, Spurs seemed to wait until the last hours of deadline day to seal their most important transfers and even if that saved the club money, it almost always cost them points by hindering their ability to enter a season with a settled squad.

Ferguson once said that dealing with Levy was ‘more painful than a hip replacement’ and it often felt as though Levy’s business acumen was a hindrance to the club in the transfer market, not a help.

Even at the start of this season, Spurs dithered and delayed over the signing of Eberechi Eze until, eventually, Arsenal snatched him from under their nose when they needed a last-minute replacement for the injured Kai Havertz. That was typical of the fate that often befell Spurs.

It may have been all that was missing. Levy’s caution, his watchfulness, his husbandry, his financial acumen all established Spurs as a club with an infrastructure second to none. Those same qualities held the club back on the pitch. Maybe now that the architect has gone, Spurs will take that final step.