Redknapp‘s Gold Cup hopes faded but the impossible dream is on to save Spurs | Cheltenham Festival 2026

Harry Redknapp is the living embodiment of Spurs’ motto, Audere est Facere: To Dare Is To Do. And on the day one improbable dream ended, with his horse The Jukebox Man fading to finish eighth in the Cheltenham Gold Cup, the 79-year-old switched his sights towards another bold adventure: saving Tottenham from relegation.

“It’s a big challenge,” said Redknapp, who managed Spurs between 2008 and 2012. “Do I need the pressure at this stage of my life? Why not? I’d give it a go. I’m not too old. I feel as fit as a fiddle. If they ask me, I think I’d do a good job.”

That is one almighty if, of course. But Redknapp also insisted afterwards that the pressure of seeing his horse carry his colours in jump racing’s most prestigious race was greater than any he had experienced during his time at Spurs.

“Managing Spurs wasn’t that stressful when I was there,” he said, with a twinkle in his eye and the broadest of smiles. “We had a good team, so it wasn’t too bad.”

Was Redknapp offering a classic come-and-get-me plea? Or was he merely playing to the gallery by telling Spurs fans what they wanted to hear? It wasn’t entirely clear. But the roar of affection he received when he was shown on the big screen beforehand showed again how popular he remains.

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Plenty of punters were prepared to show a deeper appreciation for Redknapp by backing his horse too. At the start of the autumn, The Jukebox Man was 40-1 for the Gold Cup, the same price as Spurs to win the Premier League. At the off he was a lively 7-2 third favourite.

It was shaping up to be a story for the ages. Especially as Redknapp has had racing and gambling in his blood for more than seven decades. Back in the 1950s, when betting shops were illegal, his grandmother, Maggie Brown, would take bets from housewives in the East End and pass them on to “Cyril the paperboy”, a trilby-topped bookies’ runner.

Before the race, Redknapp recalled how he would come from school, aged eight or nine, and see Maggie being taken away in a police van to Poplar police station. “Don’t worry about these bastards,” she would tell him. “I’ll be back in an hour. Your dinner’s in the oven.”

The Harry Redknapp-owned horse The Jukebox Man (left) racing in the Gold Cup. Photograph: Tom Jenkins/The Guardian

Alas, Redknapp’s hope of adding the Gold Cup to his FA Cup triumph with Portsmouth and his title of King of the Jungle in I’m A Celebrity … Get Me Out of Here, was ended by Cheltenham’s steep hill.

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For a long way he allowed himself to dream as The Jukebox Man jumped beautifully and maintained close order in second place. But when battle was joined with two fences remaining The Jukebox Man suddenly ran out of petrol as Gaelic Warrior took over and powered clear to win ahead of Jango Baie.

Afterwards, Redknapp revealed there were excuses as The Jukebox Man had missed a week’s work in the buildup to the race – but he didn’t want to make them. His trainer, Ben Pauling, also disclosed that the horse “had made a noise” and Redknapp said his runner may need a breathing operation.

“He travelled great until two out, and then he seemed to just fall in a bit of a hole,” explained Redknapp. “But overall he jumped a great run and he’s come back, hopefully safe and sound, which is the main thing.

“He missed a week’s work,” he added. “I’m not blaming it. I’m not making excuses. We didn’t say anything. But he simply just ran out of steam today. I’m not saying he would have won. The winner was amazing. Different class. He absolutely bolted up, didn’t he?”

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Harry Redknapp stands nervously outside the stable as his horse The Jukebox Man is prepared before running in the Gold Cup. Photograph: Tom Jenkins/The Guardian

Redknapp watched the race holding hands with his wife, Sandra, staring at the giant screen in the paddock. He was hoping for the best, but holding his breath at every fence.

For most of the race, there was no one else near the couple apart from a few photographers hoping to capture the glory moment. But when The Jukebox Man began to slip backwards they delivered a brutal verdict, discreetly moving away before the race was even done.

With time, though, Redknapp will surely reflect that while his horse didn’t win, his presence here has given jump racing the sort of mainstream publicity that the sport rarely receives.

For Redknapp wasn’t only on the front page of the Racing Post on Friday, he was also on Radio 4’s Today programme, waxing lyrical about how much of dream it was to have a horse with a genuine chance of winning a Gold Cup.

While he was licking his wounds, Cheltenham was announcing that a sell-out crowd of 75,000 on Friday had brought the overall attendance across the four days to 226,223, up 8,130 from last year.

The festival also said that serious efforts would be made to bring racegoers back for more dreams and adventures next year. And Redknapp, as he made clear afterwards, will be prime among them.

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