Last Updated on April 29, 2026
Harry Redknapp’s horses say a lot about him. They are honest, progressive types placed with good yards, and more than one has already carried his name into the upper reaches of jump racing.
From The Jukebox Man to the aptly named Shakem Up’Arry, his string reflects a football man who has quietly become a serious National Hunt owner.
From dugouts to parade rings
For most sports fans, Harry Redknapp will always be the touchline figure. He took West Ham into Europe, led Portsmouth to FA Cup glory in 2008, and guided Tottenham into the Champions League for the first time in the Premier League era.
Born in 1947, he enjoyed a solid playing career before moving into management, where spells at Bournemouth, West Ham, Portsmouth, Southampton, Tottenham, QPR and Birmingham City made him one of the most recognisable figures in English football.
Racing, though, has run alongside football for much of that time. Redknapp has spoken about his early interest coming from his grandmother, who worked as a bookies’ runner in the East End.
Even while dealing with the pressures of management, he followed racing closely. By the 1990s he was already involved in ownership, long before television appearances later brought him renewed attention away from football.
The Jukebox Man, the headline act
Of his current horses, The Jukebox Man is the one who has pushed Redknapp from keen owner into big-race territory. Trained by Ben Pauling, the gelding has developed into a high-class staying chaser and, just as importantly, a proper Saturday horse.
In simple terms, he is Redknapp’s most successful runner to date. Prize money has climbed comfortably past the six-figure mark, and his profile places him firmly among the better chasers of his generation.
The defining moment came in the King George VI Chase at Kempton Park Racecourse, where The Jukebox Man battled all the way to the line to land a dramatic late victory. Redknapp later admitted it was the biggest thrill he had experienced in racing, a different kind of pressure from Wembley or Old Trafford, but pressure all the same.
The Gold Cup call
The King George victory earned The Jukebox Man a place in the 2026 Cheltenham Gold Cup, the ultimate test in jump racing. Sent off at 7/2 as one of the market leaders, he travelled powerfully in the early stages under Ben Jones and was still in contention rounding the home turn. But as Gaelic Warrior, the Willie Mullins-trained favourite quickened clear, The Jukebox Man weakened approaching the last and finished eighth of ten runners, beaten 22 lengths by the winner.
Redknapp was philosophical in defeat. Speaking to ITV, he suggested a wind issue may have been a factor but was clear that no excuses were being made. “It’s been amazing,” he said. “What a week to have a runner in the Gold Cup. Winning would have been the icing on the cake, but it wasn’t meant to be. We won the second-best race, the King George at Kempton — so it’s been a wonderful season.”
The win also underlined the strength of his relationship with Pauling’s yard. It showed that Redknapp’s ownership is built on trust and patience rather than quick headlines.
Harry Redknapp’s Horses in Training
- The Jukebox Man
- The Two Harrys
- Fascinating Lips
- Icare Grandchamp
- Way Maker
- Risk It All
- Moktasaab
- Burdett Estate
- King Of Bears
The Two Harrys, a name that fits
If The Jukebox Man is the flagbearer, The Two Harrys reflects Redknapp’s enjoyment of the lighter side of racing. Sent to young trainer Harry Derham, the name is a nod to both owner and trainer, and one that feels entirely intentional.
On the track, the horse has shown promise without yet breaking through at a higher level. Placed efforts have brought modest returns, and he remains a work in progress rather than a finished article. That suits Redknapp’s style. Derham is building his career steadily, and the owner’s backing is a clear vote of confidence.
Two runs and two placed efforts suggest a horse who can find his level with time, particularly once his best trip and conditions are settled.
Fascinating Lips and Icare Grandchamp, the Moore link
Redknapp’s interests extend beyond one yard. Gary and Josh Moore train Fascinating Lips and Icare Grandchamp, both lightly raced types handled carefully.
Neither has made a major impact yet, but both fit the profile of horses given time to settle and learn. Small returns so far reflect that early stage rather than any final judgement. Together, they add depth to a string that ranges from graded performers to everyday handicappers.
The Moore connection feels natural. Gary Moore’s Sussex-based yard is known for straight dealing and hard-working jumpers, qualities that align closely with Redknapp’s football background. It is easy to see why an owner who values loyalty and effort would feel comfortable there.
Shared ownership projects
Alongside the horses he owns outright, Redknapp is also involved in a handful of partnership horses, reflecting a willingness to spread risk and enjoy racing as a shared experience rather than a solo venture.
One such runner is Way Maker, trained by Mickey Bowen and owned jointly by Harry Redknapp and Martin Gowing. The partnership fits neatly with Redknapp’s broader approach to ownership, backing smaller teams and taking a long-term view rather than chasing quick results.
He is also a part-owner of Risk It All, trained by Gary Moore and Josh Moore, alongside Keith F J Loads. The Moore operation has been in solid form recently, and the partnership adds another strand to Redknapp’s growing involvement with established National Hunt yards.
These shared interests underline a key point about Redknapp’s racing life. It is not built around a single star horse or one headline moment, but a varied mix of projects, some high-profile, others quieter, all approached with the same mix of patience and enthusiasm.
Shakem Up’Arry and the value of patience
For many racing fans, Shakem Up’Arry remains the horse most closely linked with Redknapp. Named after a West Ham terrace chant, he became a favourite long before landing a major prize.
Trained by Ben Pauling, he was often competitive in strong handicaps without quite getting his head in front on the biggest days. That changed in 2024 when he stormed home in the Plate Handicap Chase at the Cheltenham Festival, giving Redknapp his first Festival winner. Shakem Up’Arry was retired from racing in August 2025.
Earlier wins at Cheltenham had hinted at that breakthrough, but the Festival success carried extra weight. It rewarded years of patience and sticking by a horse who kept running his race.
Redknapp has been open about the financial reality of racing. Early years brought heavy losses, a reminder that ownership is rarely straightforward. His response was not to walk away, but to focus on fewer horses and higher quality.
A second career in ownership
Listening to Redknapp talk about racing, the language feels familiar. He speaks about good people, strong teams, and enjoying success together. Trainers describe him as loyal, enthusiastic and happy to let others take centre stage.
He has also been realistic about limits. Trimming numbers, focusing on Cheltenham and top-level races, and avoiding overreach all echo decisions he once made as a football manager.
From player to manager to owner of a King George winner, Redknapp has built a second sporting life without losing the traits that defined the first. The Jukebox Man, The Two Harrys, Fascinating Lips, Icare Grandchamp and the much-loved Shakem Up’Arry form a string that looks like a genuine racing operation rather than a novelty.
For someone whose grandmother once ran bets in an East End street, the move from dugouts to parade rings feels less like a surprise and more like a full circle.
