With Henry de Bromhead’s leading jockey retiring, who will race his horses at the next Cheltenham Festival? Read on to learn more about his possible partners.
Henry de Bromhead has been one of the top trainers at Prestbury Park in recent years, earning wins in major races like the Champion Hurdle, the Stayers’ Hurdle, and the Queen Mother Champion Chase. In fact, with just a few more wins, he could break into the top ten most successful Cheltenham trainers of all time.
One of the key components in de Bromhead’s winning formula, though, was his partnership with Gold Cup-winning jockey Rachael Blackmore, who retired shortly after the 2025 Cheltenham Festival. With Blackmore gone, who will race Henry de Bromhead’s horses at the 2026 edition of the event?
We’ll take a look at some of the jockeys who are likely to saddle up a de Bromhead-trained horse in the Cotswolds this year, as well as discussing some of the racers who have brought him wins in the past. Read on to learn more about the possible partnerships that could replace one of Cheltenham’s biggest pairings!
Who might race for Henry de Bromhead at Cheltenham?
While we can’t guarantee which jockeys will race for Henry de Bromhead until the Cheltenham Festival begins, there are a few riders who are likely to take the reins for his horses across the event. Here are some of the names you’re most likely to see on a de Bromhead-trained horse.
Darragh O’Keeffe
Since Blackmore’s retirement, we’ve seen Darragh O’Keeffe race plenty of Henry de Bromhead’s horses, including many rides to kick off 2026. Perhaps we could see this trend continue into the Cheltenham Festival, as O’Keeffe has already found success in the partnership, including a second-place finish at Leopardstown’s Christmas Hurdle.
In interviews, O’Keeffe has spoken about riding Bob Olinger in this year’s Stayers’ Hurdle, and has also spoken highly of other de Bromhead-trained horses, such as Quilixios and Envoi Allen. He has won races at Prestbury Park before, but he’s yet to earn a victory at the Cheltenham Festival. Could 2026 be the year he breaks the streak?
Wayne Hassett
Another jockey who could jump in the saddle for Henry de Bromhead is Wayne Hassett. The Irishman is yet to win a race at Cheltenham, but he earned multiple wins in 2025 on horses trained by de Bromhead. On Chutzpal, he won the 2025 Gold Cup Handicap at Killarney, and he racked up two victories on Stepdance at Tramore.
Hassett specialises in flat races, so it’s worth keeping an eye out for his name in the Champion Bumper betting odds, as it’s the only race competed at Cheltenham without any obstacles.
Conor Cusack
Conor Cusack made his professional flat racing debut in 2025, and he has since competed in several races for Henry de Bromhead. He raced Catena Zapata six times, earning a victory in Killarney in July 2025, before the horse was traded to Ian Donoghue a few weeks later. He has also claimed a win on Stepdance at Limerick Racecourse.
As a relative newcomer, Cusack is yet to establish himself as a Cheltenham mainstay, but he has plenty of potential to make a name for himself in the coming years. Given his history with Henry de Bromhead’s horses, it’s not out of the question that we could see him make his Prestbury Park debut this year.
Brian Hayes
Rounding out our list of prospective jockeys for Henry de Bromhead, there’s also a chance that Brian Hayes will compete for the Irish trainer. Although Hayes has earned most of his wins in the 2025-26 season on Willie Mullins-trained horses, including four wins on May Call You Back, he has also competed on horses from de Bromhead’s stables, such as Wonleg and Marv Michael.
Hayes is no stranger to Cheltenham success, having won the 2023 Mares’ Chase on Impervious. He seems to be in good form in 2026 too, earning major wins at Fairyhouse and Naas in January, so there’s every chance he could find himself placing first in the Cotswolds once again.
Who has been Henry de Bromhead’s most successful jockey at Cheltenham?
Henry de Bromhead’s most successful Cheltenham jockey, without a doubt, is Rachael Blackmore. As a female rider in a sport mostly dominated by men, Blackmore made history at the Festival by becoming the first woman to claim the title of leading jockey. She was also the first female rider to win the Cheltenham Gold Cup, racing A Plus Tard to victory in 2022.
When it comes to Blackmore’s most successful horses, Honeysuckle was especially noteworthy; the pair won consecutive Champion Hurdles in 2021 and 2022, as well as the Mares’ Hurdle twice in 2020 and 2023. Bob Olinger was also a prolific winner for Blackmore and de Bromhead, winning the 2021 Baring Bingham Novices’ Hurdle, the 2022 Golden Miller Novices’ Chase, and the 2025 Stayers’ Hurdle.
Some of Henry de Bromhead’s other successful jockeys at Cheltenham include Jack Kennedy, who won the 2021 Gold Cup on Minella Indo. This earned de Bromhead his first victory in Cheltenham’s biggest event, before Blackmore would make him a two-time winner a year later. Aidan Coleman has also claimed multiple Cheltenham victories for de Bromhead, such as the 2020 Arkle and 2021 Queen Mother Champion Chase, both on Put The Kettle On.
In which races are we likely to see Henry de Bromhead’s jockeys at Cheltenham?
With so many horses in his stables, Henry de Bromhead is likely to be competing in many of Cheltenham’s most popular races. He has confirmed that Envoi Allen will race in his final Gold Cup, where he’s currently a strong outside contender in the ante-post betting odds.
Downmexicoway is also expected to compete in the Arkle Chase, while Bob Olinger is one of the favourites to retain his 2025 title in the Stayers’ Hurdle betting odds. De Bromhead also has multiple horses (Inthepocket, Quilixios, Captain Guinness) who are expected to compete in the Queen Mother Champion Chase.
Will we see more Henry de Bromhead winners at Cheltenham 2026?
The list of Henry de Bromhead’s Cheltenham winners is already extensive, with the Irishman having trained more than 20 victors over the course of his career. That list could grow even larger this year, though, as some of de Bromhead’s horses could claim even more victories.
Quilixios seems to be a strong competitor in the Champion Chase, while Echoing Silence is one of the favourites in the Mares’ Novices Hurdle betting. July Flower is also among the leaders in the 2026 Mares’ Chase odds, while Heart Wood and Envoi Allen both have the opportunity to cause a big upset in the Cheltenham Gold Cup betting, as many eyes will be glued to the match-up between Inothewayurthinkin and Galopin Des Champs this year.
