‘I’ve been playing the Gold Cup over in my dreams,’ says Harry Redknapp as The Jukebox Man gears up for Cheltenham

WHEN Harry Redknapp nods off at night, he keeps having the same recurring dream.

His beloved horse, The Jukebox Man, is galloping clear over the last and up the Cheltenham hill to win the Gold Cup.

For Redknapp, whose love for the Cheltenham Festival and National Hunt racing runs as deep as his East End roots, it’s as exciting as anything he experienced during his years in football.

This isn’t just some wild fantasy, mind. In just a few days time this dream could become very real indeed.

“I have been playing the race over in my dreams at night, I can see him coming to the last in the lead in the Gold Cup. Please God it comes true,” he says.

Football has been Redknapp’s life since he was knee-high to a grasshopper – but even the beautiful game is playing second fiddle to jumps racing at the minute.

The former Spurs, West Ham and Portsmouth manager has owned horses for the thick end of 40 years, but he’s never been on a ride quite like this.

Not only did The Jukebox Man give him a first Grade 1 win as an owner at Kempton on Boxing Day in 2024, a year later he was back to win one of the most exciting King George VI Chases in history.

The long wait for the judge to call the result of THAT four-way photo-finish won’t have done any good for Redknapp’s ticker, but as Jukebox’s name sounded over the tannoy he let out the kind of roar usually reserved for a 94th-minute winner.

Redknapp said: “In the race I keep thinking he’s beat, he’s beat, and then he comes again. He was so tough.

“It was fantastic, my family were there with me and it was an amazing day.

“My wife Sandra was worried about coming because she thought she’d be bad luck. I’d say she’s good luck, now!

“I’ve had an awful lot of horses, I’ve still got an awful lot, but this one has taken us to places that you only dream about. He wouldn’t be for sale at any price.”

The world of top-flight horse racing is a far-cry from where Redknapp, 79, grew up in Poplar.

But betting on racing was a part of daily family life – his nan worked as a runner for the local bookie, Cyril the paperboy, and was nicked more than a few times by the police.

And that betting culture carried on during his days as a player and a manager.

He said: “I’ve always been interested in racing, I grew up with it, listening to the Grand National around the radio and going back to my mum winning the sweep at the cake factory she worked in with Foinavon. I think we won £3.50 which was a lot of money to us in those days.

“I went to West Ham as a player at 15 and it was full of punters. We had a top player called Johnny Byrne and his warm-up the day before a match was to sit on the side with a cup of tea and The Sporting Life. Then on a Saturday he’d go and bang in a couple of goals!

“I do a lot of these question and answer circuits now in the theatres around the country, and people ask me about The Jukebox Man more than football.

“If I see some of the boys who played for me, they all want to talk about it.”

Redknapp had several visits to Cheltenham over the years with his players, even crediting a team-building booze-up at the Festival during his West Ham days for helping them escape relegation.

There was one year, however, when he found out a group of Spurs players had organised a secret trip.

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He laughed: “We went on the Wednesday on the team bus as a group and had a great day out.

“Then I found out Jonathan Woodgate had gone and organised a helicopter to take another group of them there, Crouchy and Jamie O’Hara and a few others, on the Thursday of Cheltenham.

“I went and told them they couldn’t go – then they offered me a seat on the chopper and I said, ‘yeah, go on then!’”

Of course, Redknapp is used to the full glare of the media spotlight, but he loves nothing more than the peace and quiet of Ben Pauling’s stable in the Cotswolds, watching his horses on the gallops.

It’s a little over three weeks until the Gold Cup when we catch up and he is here paying his horse a visit with old pal ‘Dave the Magician’ in tow.

He is an actual magician, who entertains the hospitality boxes at Stamford Bridge every other Saturday, and he’s conjured a few carrots from up his sleeve to feed The Jukebox Man .

“Don’t give him too many, Dave, he’ll be too fat and won’t be able to run!” Redknapp blasts.

In truth, The Jukebox Man doesn’t even need Dave’s magic touch to win the Gold Cup. He is right in the mix.

The run-in from the last fence at Kempton is barely 150 yards, and very few horses manage to get back up to win once they’ve been headed.

The eight-year-old managed to do just that, and not against any old opposition. He rallied to beat Gaelic Warrior and Jango Baie, plus the defending King George winner Banbridge.

It’s top-class form and everything about the horse suggests he is going to love the test of the Gold Cup, with it’s extra two and a half furlongs.

Redknapp said: “I’m a pessimist, to be honest, and going to Kempton I was thinking Ben was talking rubbish, there was no way we could win a King George. But he was so bullish and he was right.

“And he is even more confident that the Gold Cup will suit him better than the King George at Kempton.

“It’s a tough race and a very open race but I wouldn’t swap him for anything. The excitement is really building and I can’t wait.

“Ben Jones is a terrific jockey, him and Ben Pauling have so much belief in the horse.”

Harry takes a big swig of tea in the kitchen at Pauling’s yard. I ask how the nerves are going to be on Gold Cup morning – on a par with taking Pompey to Wembley for the FA Cup final?

He smiles: “It’ll be very similar. I’ll obviously be very nervous and probably more nervous watching a race than I am even at football on the touchline. You get nervous at every jump.

“I hold my breath, you know. It’s a nerve-racking experience. In the dugout you can change things if you’re not happy with how a game is going.

“In racing there’s nothing you can do, it’s out of your hands and you just pray they come back safe and sound and run a good race.

“You know what you can do. Ben has done all the work and the staff with the horse. You’re just relying on the jockey and the horse doing the job.”

Redknapp already has a Cheltenham Festival winner to his name, having watched his pride and joy Shakem Up’arry win the Plate in 2024.

The following day, The Jukebox Man was beaten in heartbreaking fashion in the Albert Bartlett Novices’ Hurdle, and the Gold Cup will be his first visit to Cheltenham since then. Redknapp said: “I’ve had horses with Ben for a long time now, we get on great.

“We’ve had some good days, I had Shakem Up’arry winning at the Festival for me, and Jukebox was chinned on the line the next day.

“I was gutted but Ben Pauling said to me, ‘just wait until he jumps a fence’, and he was right.

“It would be unbelievable to win a Gold Cup, it would be incredible. Cheltenham is the World Cup of jumps racing and I can’t wait.

“To win the King George was beyond my wildest dreams for sure, but to win a Gold Cup would be amazing.

“He goes there with a real chance. I had a dream the night before the King George and that came true, now I am dreaming about the Gold Cup.”