Harry Redknapp is on the brink of achieving a sporting dream as one of his horses runs today in the Cheltenham Gold Cup.
Winning one of the most prestigious races of the horseracing calendar would give Redknapp closer on a journey of love, respect and enjoyment that began with his grandmother, Maggie Brown, who was a bookmaker's runner in London's East End.
Redknapp explained how his life has always intertwined with horseracing and how, from the age of eight, his interest in the sport has only grown.
“I've always been interested from eight years of age. My nan was a bookies’ runner in the East End of London. I grew up with it, listening to the Grand National around the radio and going back to my mum winning the sweepstake at the cake factory she worked in the year Foinavon won. I've always loved it,” said the 79-year-old former football manager.
“I went to West Ham as a player at 15 and it was full of punters – they all loved a bet and The Sporting Life would be in the dressing room,” he added.
After success in football, Redknapp followed the likes of Sir Alex Ferguson into racehorse ownership but more for the love of the sport than on-course success.
During his career as a racehorse owner, Redknapp has bought 23 horses outright, ably nudged in the right direction by his team of trainers and stable hands.
He currently has seven on his books as well as interests in other horses, such as Taurus Bay who ran at Cheltenham on Wednesday, Way Maker and Risk It All , through joint ownership schemes.
The horses Redknapp owns also vary in quality with The Jukebox Man his best horse in the current coterie and the one going for glory in the Gold Cup today.
Harry Redknapp’s horses
|
1. The Jukebox Man
|
Trained by Ben Pauling, The Jukebox Man is the horse that has propelled Redknapp into the upper crust of racehorse ownership. The gelding is a high-class staying chaser and one competitive enough to win champion races. This was proven in December 2025 when he clinched the King George VI Chase at Kempton in a field featuring the likes of Gaelic Warrior and Jango Baie who also run in today’s Gold Cup.
He is also the epitome of Redknapp’s partnership with trainer Ben Pauling whose yard is on the rise after years of backing, trust and patience from Redknapp. Already, The Jukebox Man has earned Redknapp an estimated £270,000 in prize money which is over £100,000 more than his second most successful horse.
That would be Shakem Up’Arry who was retired in August 2025 at the age of 12 years old. Shakem Up’Arry is perhaps the most famous of the horses owned by Redknapp after he triumphed in the 2024 Plate Handicap Chase to earn Redknapp his first ever winner at the Cheltenham Festival.
Another of note is The Two Harrys. He has been sent to to young trainer Harry Derham and was named after both owner and trainer. On the track, the horse has shown promise without yet breaking through and has brought in modest returns, after two placed finishes.
Despite his small stable Redknapp’s love for horseracing is undiminished and he is still in touch with his roots despite now being in with a chance at landing the Gold Cup.
"It really would be lovely, but I'm not counting my chickens, I'm just hopeful,” Redknapp said of The Jukebox Man’s chances.
“It's a dream to have a horse to run in the Gold Cup and go there with a chance. I've had an awful lot of horses, still got an awful lot, but this one has taken us to places that you only dream about as a racehorse owner. He's my dream, he's not for sale and he wouldn't be for sale at any price.
“I'm not saying we're going to win it we've got a serious horse, it's an open race and I think we've got as good a chance as anything.”
Harry Redknapp could achieve his sporting dream this week – and it’s nothing to do with football
Heart Wood seizes Cheltenham Festival redemption but Fact To File withdrawal raises vital question
A tale of two Cheltenhams: Cheaper pints and Prosecco aplenty – amid abundance of lavish luxury
Harry Redknapp may achieve his sporting dream – and it’s nothing to do with football
Cheltenham Gold Cup betting offers: Free bets, odds boosts & extra places
Bet365 Cheltenham offer 2026: £30 welcome bonus & Gaelic Warrior super boost
