‘Sad’ Jockey Kim Bailey Has Announced the Retirement of Cheltenham Festival Hero Just When ‘Everything Seemed to Be Going Well’
In the picturesque Cotswolds, where rolling hills meet the thunder of hooves, a bittersweet announcement has rippled through the world of National Hunt racing. Kim Bailey, the veteran trainer whose name evokes triumphs like the 1995 Cheltenham Gold Cup with Master Oats and the Grand National glory of Mr Frisk, has confirmed the retirement of one of his most cherished charges: Chianti Classico. The nine-year-old gelding, a darling of the Festival crowds, bowed out not with a blaze of glory but with a quiet nod to the realities of the sport—prioritizing welfare over one last gallant charge toward the Cotswold Chase or even the looming Gold Cup.
Bailey’s voice carried a palpable heaviness when he shared the news on his yard’s blog earlier this week. “It’s sad, really,” he wrote, capturing the sentiment that has left fans and fellow trainers murmuring in pubs from Lambourn to Prestbury Park. Chianti Classico, affectionately known as “CC” in the yard, had been the embodiment of resilience and joy. Just months ago, everything did seem to be aligning for another chapter in his storied career. The horse had returned to light exercise over the summer, his coat gleaming under the July sun, and whispers of a comeback had electrified the racing grapevine. Bailey himself admitted the optimism: scans showed healing progress on that troublesome left-hind tendon, torn in the unforgiving December chill at Cheltenham last year. Vets nodded approvingly; the team dared to dream of spring pastures not just for grazing, but for racing.
Yet, as autumn leaves began to carpet the gallops at Thorndale Farm, a backward step shattered the idyll. Recent assessments revealed that the injury, while mending, had not yielded enough to withstand the rigors of top-level chasing. “The welfare of the horse is the most important thing,” Bailey stated firmly, his words a mantra for an industry increasingly under the microscope for equine care. “We’ve decided the most sensible thing to do is retire him and let him have a wonderful life away from racing, which I’m sure he will.” It’s a decision that echoes the trainer’s philosophy—forged over four decades of saddling more than 1,500 winners—where the thrill of victory yields to the quiet dignity of a well-earned rest.
Chianti Classico’s journey was nothing short of a fairy tale scripted for the silver screen. Acquired by Bailey and owner Aiden Murphy from trainer Ben Halsall at the Newmarket Tattersalls sales, the horse quickly caught the eye of high-profile syndicate members Sir Francis Brooke and Richard Pilkington. Brooke, the chairman of Ascot and His Majesty’s Representative there, brought a touch of royal glamour to the ownership group. Their faith paid dividends in spades. CC’s breakthrough came in the autumn of 2023, but it was November of the following year that etched him into lore. Carrying a hefty 12 stone—the top weight—in the prestigious £100,000 Sodexo Gold Cup Handicap Chase at Ascot, he surged to victory amid cheers that seemed to shake the historic stands. From Brooke’s balcony perch, the win unfolded like a coronation, a moment of “sheer joy” that Bailey recalls with a wistful smile. “We were all there that day,” he wrote, “and to watch CC cross the line… it was magic.”
But it was the Cheltenham Festival in March 2024 that crowned him a hero. In the Ultima Handicap Chase, a grueling three-mile test on the New Course, Chianti Classico dug deep to claim the prize, fending off challengers in a photo-finish that had the Prestbury Park roar reaching fever pitch. Jockey David Bass, aboard for that triumph, later described the ride as “electric,” with CC’s powerful stride eating up the uphill finish. The victory propelled dreams of a Gold Cup tilt this winter, positioning him as a dark horse in the staying chase division. Pundits speculated on his potential in the Cotswold Chase at trials day in January, or even a bold Gold Cup bid in March. At 20-1 in early ante-post markets, he was the punter’s delight—a horse whose exuberance mirrored the unbridled spirit of jump racing.
That exuberance, however, masked the fragility beneath. Post-Ascot, CC’s next outing at Cheltenham’s December meeting ended in lameness, the diagnosis a torn tendon that sidelined him for nearly a year. Such injuries are the scourge of chasers, often spelling the end for equine stars who push their bodies to the limit over unforgiving fences. Bailey’s yard, known for its state-of-the-art facilities and individualized care, rallied with laser therapy, hydrotherapy pools, and endless patience. Summer brought hope: CC trotted sound on the walker, nuzzled his grooms with that trademark gentleness. “We all just loved his exuberance for life and racing,” Bailey reflected. It was as if the horse, with his bay coat and kind eyes, embodied the very soul of the sport—fierce in battle, tender in repose.
Now, as October’s chill sets in, Chianti Classico’s stall at Thorndale Farm will echo with absence. His photo joins the pantheon on Bailey’s office wall, alongside portraits of past legends like Alderbrook, the 1995 Champion Hurdle winner who also graced these stables. “It’s something I wasn’t looking forward to putting up,” Bailey confessed, “as they only go on the wall when they retire. But what a life, what a horse, and what pleasure he has given us all.” The trainer, at 68, remains a pillar of the game, his yard buzzing with prospects like the promising novices in his 2025-26 string. Yet this retirement stings sharper, coming when the stars aligned for more.
The racing community has rallied with tributes. Sir Francis Brooke hailed CC as “a once-in-a-lifetime partner,” while jockeys’ forums buzz with fond recollections of his generous jumping style. In an era where welfare debates rage—from the Grand National’s reinvention to calls for shorter careers—Bailey’s choice underscores a shift. Horses like CC, who gave their all, deserve paddocks over pressures. As he transitions to a second act—perhaps foxhunting in the Cotswolds or simply grazing under Brooke’s watchful eye—his legacy endures. He reminded us that in racing, the greatest victories aren’t always on the scoreboard, but in the hearts of those who cheered him home.
For Bailey, the road ahead holds no pauses. With the Jumps season firing up at Chepstow and Newton Abbot, his team eyes redemption. But for now, a collective sigh hangs over the yard. Chianti Classico’s retirement isn’t an end; it’s a grateful farewell to a hero who raced with fire and retired with grace. In the unpredictable dance of trainer and thoroughbred, sometimes the kindest curtain call comes just when the encore felt within reach.
