Glenn Hoddle claims there’s one ‘massive mistake’ Daniel Levy made at Tottenham, it cost a trophy

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In the 23 years that Daniel Levy has been at Tottenham, there has been a mix of successes and failures made from big decisions at the very top.

Spurs have progressed from being a more mid-table outfit in the early years of the Premier League to one that regularly made the Champions League through the 2010s and into the 2020s.

That is all while being on a relatively modest budget, but in that time there has been very few ways to measure that success.

Tottenham fans want those trophies to have a tangible memory of those good moments on the pitch, something that can’t be satisfied with just a top-four finish.

It’s what Ange Postecoglou is looking to deliver, with Spurs’ recent 2-1 victory over Manchester City in the EFL Cup giving them a chance of doing just that.

The trophy wait could’ve been ended much sooner though, according to former player and manager Glenn Hoddle.

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Glenn Hoddle discusses Tottenham sacking Jose Mourinho

If there’s one area where Hoddle thinks Levy has made a mistake over the years, it surrounds the handling of ex-manager Jose Mourinho.

The Portuguese coach was struggling with Tottenham in the 2020/21 season, but he had got them in a position to win a trophy.

An EFL Cup final against Manchester City was setup by Mourinho, but he was sacked just days before taking to the pitch at Wembley Stadium.

Instead, interim boss Ryan Mason took charge of his first game against the brains of Pep Guardiola – who is many years his senior in management.

Spurs lost and were unable to land that elusive trophy, with Hoddle claiming it was a mistake to sack Mourinho.

He said on The Overlap: “I think there’s a massive mistake that Daniel Levy made, Jose [Mourinho] gets them to a cup final, the League Cup final which was the first he won at Chelsea, but it’s a stepping stone.

“Sacked him on the Monday, now that don’t make sense to me and it never will. So I don’t understand that at all, you bring somebody in to win a trophy and he has a good record against Pep [Guardiola] as well, albeit against Man City.

“And then put, with no disrespect, a young coach in that’s not had any experience. I mean that just wow.”

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Were Tottenham right to sack Jose Mourinho?

All these years on, the debate that rages around Mourinho and the end of his time at Tottenham still rumbles on.

In some part, Spurs strayed away from what brought them to the top under Mauricio Pochettino by bringing in the Portuguese boss.

Switching from their dynamic style with youngsters impressing on the pitch, the serial winner took a different approach.

With that win-first look at things, there was less pressure to build a long-term plan and it left Spurs in dismay after.

That was only accentuated by landing Antonio Conte, who implemented more of the same with a short-term boost and long-term fall.

So, in the long run, perhaps moving on from Mourinho was the right thing, with Postecoglou looking to add a style of play while bringing through youngsters to become some of the best in the world.

However, in terms of ending that trophy pain, moving on from the Portuguese boss was definitely a mistake.

Mourinho has a good record against Guardiola over the years and with a style of play that could counter on Man City, it would’ve made sense to have him in charge.

Whether there were concerns that a trophy would keep him in post longer is up for debate, though Erik ten Hag’s era at Manchester United can perhaps point towards the outcome of that.

In all, Tottenham are still looking to end the long wait for a trophy, but are doing so while elevating performances in the league and the squad.

There are no shortcuts to success in the long run, something Tottenham have learned the hard way.