Harry Redknapp has spent most of his life around sport, yet even after decades in football the build-up to the Cheltenham Gold Cup still carries a different kind of anticipation.
This year one of Harry Redknapp’s horses will take its place in the Festival’s most famous race.
The Jukebox Man, trained by Ben Pauling and ridden by Ben Jones, lines up in the Cheltenham Gold Cup on Friday afternoon, giving the former Tottenham and Portsmouth manager a runner in what many regard as the biggest race in jump racing alongside the Grand National.
For followers of the sport, and anyone keeping track of Harry Redknapp horses, the gelding is the most accomplished runner to carry Redknapp’s colours so far.
The Gold Cup, run over three miles and two furlongs on Cheltenham’s demanding New Course, remains the highlight of the Festival card.
Reaching this stage is rarely straightforward. Even wealthy owners can spend decades trying to get a horse into the race without ever managing it. Redknapp’s route has been quieter and more gradual, built on a small but carefully placed group of horses spread across several yards.
Among them all, The Jukebox Man has emerged as the headline act.
The Horse That Changed Everything
When The Jukebox Man first appeared as a novice he looked promising rather than exceptional.
He was a big, scopey horse with plenty of stamina and an appetite for jumping. Ben Pauling’s yard always believed that chasing would bring out the best in him, and that belief quickly proved justified.
Over fences he developed a bold, attacking style.
He meets his obstacles with speed and confidence, the kind of jumping that keeps a horse travelling smoothly through a race. Whether taking a long stride or popping one on a short step, he tends to land running, which allows him to build pressure on rivals.
The performances steadily improved.
Then came the race that transformed his reputation.
A King George Breakthrough
The King George VI Chase at Kempton on Boxing Day is one of the most prestigious races in the jumping calendar outside Cheltenham itself.
Winning it immediately places a horse in the Gold Cup conversation.
The Jukebox Man arrived at Kempton with solid form but still had something to prove at the very top level. What followed was the performance that confirmed his class.
Turning for home he looked briefly under pressure, but once asked to find an effort he responded with real determination. In the closing stages he battled back to claim victory after a thrilling duel, showing both stamina and courage.
Trainer Ben Pauling later described the race as a dream result for the yard. He spoke about the horse’s huge engine and the heart he showed in the closing stages, qualities that are essential for any chaser with Gold Cup ambitions.
For Redknapp it was the biggest moment of his ownership career so far.
The victory turned The Jukebox Man from a promising staying chaser into a genuine contender for jump racing’s greatest prize.
Cheltenham Success Already Secured
The Jukebox Man is not the first horse to give Redknapp a special Cheltenham memory.
That honour belongs to Shakem Up’Arry, a horse who became a favourite among racing fans long before landing his biggest victory.
Named after a chant familiar to West Ham supporters, Shakem Up’Arry spent several seasons running well in competitive handicaps without quite landing a major prize.
That changed at the 2024 Cheltenham Festival, when he stormed home to win the Plate Handicap Chase.
The victory meant a great deal to Redknapp. Cheltenham winners always matter, but Festival winners carry extra significance. It rewarded the patience of sticking with a horse who kept running honest races in strong company.
Shakem Up’Arry was retired in August 2025, his place in the story secure.
Now the colours return to Cheltenham with an even bigger opportunity.
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A Place in the Gold Cup
The Cheltenham Gold Cup remains the race every jumps owner measures success against.
Run over three miles and two furlongs, it demands stamina, accurate jumping and the ability to handle Cheltenham’s famous uphill finish.
The 2026 field contains several established Grade 1 performers.
Gaelic Warrior, Grey Dawning, Haiti Couleurs, Jango Baie and Inothewayurthinkin all arrive with strong credentials in the staying chase division.
Into that company steps The Jukebox Man.
His profile commands respect. He arrives unbeaten over fences, already a King George winner, and partnered by a jockey who knows him well.
Ben Jones has ridden the horse throughout much of his rise. His calm style suits the gelding’s bold jumping approach, allowing him to settle early before gradually building pressure.
Gold Cups are rarely simple races. The pace is relentless and the final climb up the hill has ended the hopes of many talented horses.
Yet if The Jukebox Man reproduces the performance he showed at Kempton, he has every chance of remaining involved when the race begins to unfold in the closing stages.
For Redknapp, simply having a runner is already a remarkable achievement.
Winning it would place him among the sport’s most fortunate owners.
The betting suggests that dream is not unrealistic. The Jukebox Man currently sits at around 3/1 joint-favourite alongside Gaelic Warrior, a reflection of the strength of his King George victory earlier in the season.
Jango Baie is close behind in the market at around 4/1, while Haiti Couleurs at roughly 6/1 also commands serious respect after a sequence of strong staying chase performances.
With several proven Grade 1 chasers lining up, it looks a properly competitive Gold Cup. But with his unbeaten chasing record and big-race form already on the board, The Jukebox Man has every right to be prominent in the betting and firmly in the conversation.
From the Dugout to the Parade Ring
Redknapp’s reputation was forged on football touchlines rather than racecourses.
Born in 1947, he enjoyed a solid playing career before moving into management, where his instinctive style and straight-talking personality made him one of the most recognisable figures in English football. His managerial career took him through Bournemouth, West Ham United, Portsmouth, Southampton, Tottenham Hotspur, Queens Park Rangers and Birmingham City.
The high point came in 2008 when Portsmouth lifted the FA Cup, while Tottenham’s qualification for the Champions League two years later confirmed his reputation as one of the game’s most experienced managers.
Racing, though, had always been part of the background.
Redknapp grew up around betting shops and race talk in London’s East End. His grandmother worked as a bookmaker’s runner, and horses were a regular topic of conversation long before he became a football manager.
Even during his busiest years in football he kept a close eye on the sport. Ownership arrived gradually, beginning with small shares before expanding into a broader interest.
Today, when people discuss Harry Redknapp horses, the conversation usually turns to a small group that includes The Jukebox Man, The Two Harrys, Fascinating Lips, Icare Grandchamp, Way Maker, Risk It All, Moktasaab, Burdett Estate and King Of Bears.
The string is not large by racing standards, but it has become increasingly competitive.
A small but serious racing team
For many owners, racing becomes more enjoyable once the scale is right.
Redknapp has often spoken about learning that lesson the hard way. The early years of ownership brought the same experience many first-time owners face: plenty of enthusiasm, but plenty of losing runs as well.
Over time he adjusted his approach.
Rather than spreading himself across too many horses, he focused on keeping a smaller team and placing them with trainers he trusted.
Taken together, the group reflects an owner who enjoys the sport for its people as much as the results.
But every racing string eventually produces one horse who lifts it to another level.
For Redknapp, that horse is The Jukebox Man, who represents the most exciting chapter of that journey so far.
For a man who has spent a lifetime in sport, watching one of his horses line up in the Cheltenham Gold Cup offers a different kind of thrill.
And if the race unfolds kindly, Harry Redknapp may yet find himself celebrating on the biggest stage jump racing has to offer.
Shakem Up’Arry!
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