Former football manager Harry Redknapp stands on the cusp of a lifelong sporting ambition as his star horse, The Jukebox Man, competes in the prestigious Cheltenham Gold Cup today. A triumph in one of horseracing's most celebrated events would crown a journey fueled by passion, heritage, and sheer enjoyment, tracing back to his grandmother, Maggie Brown, who worked as a bookmaker's runner in London's East End.
A Lifelong Passion for Racing
Redknapp, 79, has detailed how his existence has always been intertwined with the world of horse racing. His fascination with the sport ignited at the tender age of eight and has only intensified over the decades. "I've always been interested from eight years of age. My nan was a bookies' runner in the East End of London," Redknapp recounted. "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."
He further explained how his early football career at West Ham United immersed him in a culture of betting enthusiasts. "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. Following a successful tenure in football management, Redknapp transitioned into racehorse ownership, inspired by figures like Sir Alex Ferguson, though his motivation stems more from adoration for the sport than a relentless pursuit of victory.
The Current Stable: Seven Horses on the Books
Throughout his ownership career, Redknapp has purchased 23 horses outright, guided by a dedicated team of trainers and stable hands. Presently, he maintains seven horses in his personal stable, alongside interests in other steeds like Taurus Bay, Way Maker, and Risk It All through joint ownership arrangements. The quality within his coterie varies, with The Jukebox Man emerging as the standout contender and his prime hope for Gold Cup glory today.
Harry Redknapp's Horses
- The Jukebox Man
- Fascinating Lips
- Icare Grandchamp
- King of Bears
- Burdett Estate
- Moktasaab
- The Two Harrys
The Jukebox Man: A Dream Horse
Trained by Ben Pauling, The Jukebox Man has elevated Redknapp into the elite echelons of racehorse ownership. This high-class staying chaser has demonstrated championship-caliber competitiveness, notably securing the King George VI Chase at Kempton in December 2025 against formidable rivals like Gaelic Warrior and Jango Baie, who also feature in today's Gold Cup. The gelding embodies the fruitful partnership between Redknapp and Pauling, a collaboration built on years of unwavering support, trust, and patience.
To date, The Jukebox Man has amassed an estimated £270,000 in prize money for Redknapp, surpassing his second most successful horse by over £100,000. "It really would be lovely, but I'm not counting my chickens, I'm just hopeful," Redknapp remarked regarding his horse's prospects. "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."
Other Notable Horses in the Stable
Redknapp's second most successful horse is Shakem Up'Arry, retired in August 2025 at age 12. This steed gained fame by winning the 2024 Plate Handicap Chase, granting Redknapp his inaugural Cheltenham Festival victory. Another noteworthy entry is The Two Harrys, named after both owner and trainer Harry Derham. While this horse has displayed potential with two placed finishes, it has yet to achieve a breakthrough, yielding modest returns thus far.
Roots and Realistic Expectations
Despite operating a relatively small stable, Redknapp's ardor for horseracing remains undiminished, and he stays connected to his humble origins even as he vies for Gold Cup honors. Reflecting on The Jukebox Man's chances, he stated, "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." His journey from listening to races on the radio to potentially clinching one of racing's top prizes underscores a profound, enduring love for the sport.
