Cheltenham Festival 2026: Harry Redknapp eyes Jukebox Man win Gold Cup

From “putting a pen in a couple” during the flutter of youth to owning a King George VI Chase winner and potential Cheltenham Gold Cup winner, Harry Redknapp has come a long way in horse racing.

The FA Cup-winning football manager’s love of the sport can be traced back to his grandmother Maggie Brown, who worked in a bookmaker’s office in London’s East End, at a time when betting shops and off-field betting were illegal.

On Friday, his horse Jukebox Man will attempt to add a Cheltenham masterpiece to his King George win in December.

The King George VI Chase is the biggest jumps race of the pre-Cheltenham Festival season, while the Jockey Club describes the Gold Cup as the most prestigious steeplechase race in the world.

After sealing a final win at Kempton Park on Boxing Day to knock out 2024 King George Award winners Banbridge and favorites Gaelic Warrior 9-4, Redknapp said: “We’ve reached the Champions League today.”

But can he win the Champions League equivalent of jump racing?

“We have a chance, but it’s a tough race,” Redknapp told BBC Radio 5 Live.

Among those standing in his way are Gaelic Warrior, Jango Baie, Haiti Couleur and last year’s winner Inothewayurthinkin.

“Just to have a runner in the Gold Cup is a dream come true,” Redknapp said.

“We had a lot of fun with Jukebox Man, who won the King George on Boxing Day, one of the most popular races on the racing calendar.

“Going to the Gold Cup and getting a runner who has little chance is fantastic.”

The win will be the crowning moment of a 70-year love affair with the sport that began during childhood.

“My grandmother will take the bets,” he said. “I was going out to dinner at my school when I was eight or nine years old, and I was put in the back of a police car and taken to Poplar Police Station.”

Nan Redknapp would ask him to “put a pen in a couple” and that would be her bets for the day.

Although he loved the sport, he was never tempted to ride horses – “not for all the money in the world”.

“They were injured, these riders, and then they came back about three weeks later,” he said.

“They’re not like football players, are they?”

Redknapp owns shares in 26 HP.

“You’re not always successful,” he said.

“For every Shakem Up’arry, Jukebox Man, and Taurus Bay, there are plenty of others who never did anything at all.”