By Victoria Goff 

Only three riders in history have ever won the Hickstead Derby and the King George V Gold Cup in the same year. The first was David Broome, who won both classes with Mister Softee in 1966. Then came Harvey Smith, who did the double with Mattie Brown in 1970. Last year, a new rider joined their ranks, and that’s Robert Whitaker. 

Yorkshireman Robert moved to a new base just minutes from the All England Jumping Course a few years ago, and it’s fair to say that his local showground has proved to be extremely happy hunting ground for him ever since. His golden run began back in 2023, when he won the King George V Gold Cup with Vermento (Argento x Skippy II), a horse bred by his father John. Then he joined his Dad on the winning team for the Agria Nations Cup of Great Britain in 2024, the first time Robert had been on a victorious Hickstead team since 2004. Then came last year, an annus mirabilis by any showjumper’s standards, when Robert won the Al Shira’aa Derby for the first time with Gentlemen VH Veldhof (Quite Easy I x Calido I), and followed it by regaining the Al Shira’aa King George V Gold Cup in July with Vermento.

They've been great owners for me, and I’d said to them if they bought ‘Gent’ he'd probably win the Derby – and it actually happened!

At the end of the 2024 season, Robert had advised Vermento’s owners Caroline and Stephen Blatchford to purchase the veteran campaigner Gentlemen VH Veldhof, a decision that really paid off. “They've been great owners for me, and I’d said to them if they bought ‘Gent’ he'd probably win the Derby – and it actually happened!” says Robert. 

It was unusual for Robert to be buying a horse at that stage of its career – Gentlemen was nearly 19 when he arrived at Robert’s yard, having already been competed internationally by no less than 10 different riders including Marc Houtzager, Jack and Michael Whitaker, David Simpson, Joe Clayton and Tim Gredley. But he did have Hickstead form, having won the Queen Elizabeth II Cup back in 2019 with Simpson, and he’d been round the Al Shira’aa Derby several times, most notably finishing sixth with Joe Clayton in 2024. 

Older horses have a great record in the Hickstead Derby – you only have to look at John Whitaker’s rides Welham and Gammon, who won the class at the ages of 21 and 20 respectively. Robert had been placed in the Derby on several occasions, but he had lacked the horsepower to join his Dad, uncle Michael and cousin William on the roll of honour. 

“I've always wanted to win the Derby,” says Robert. “I would say it is one crossed off my bucket list, because I've been coming to Hickstead all my life, and to win that class means everything, really. I've never had the right horse for it, I've tried many times and I failed miserably a lot of those times! It's never easy to jump clear round in the Derby, but it's definitely easier when you’re on the right horse, and Gentlemen made my life easy that day.” 

I would say it is one crossed off my bucket list, because I've been coming to Hickstead all my life, and to win that class means everything, really.

Some years, the Al Shira’aa Derby can be won on a single clear, but last year three riders went clear to go through to the jump-off. The gauntlet had been laid down by the very first rider to go, Sammie-Jo Coffin, who delivered a superb clear on the exuberant Chaccomo Blue (Vigo d'Arsouilles x Lux Z). It wasn’t until a second clear from Robert and Gentlemen, drawn 20th, that a jump-off was guaranteed, with Robert’s cousin William Whitaker and the previous year’s runner up Flamboyant III (Cardento x Niveau) joining them a few horses later. 

In the jump-off, Sammie-Jo picked up an early four faults at the white oxer at fence two, giving Robert a little bit of breathing space. Robert also picked up four faults at the Derby rails, but he crossed the finish line some 8sec faster than Sammie-Jo to take the lead. It was more than enough to put pressure on William, who was bidding for a second Derby title. 

“I knew William’s horse is a bit of a bigger, slower type, whereas Gent is actually quite quick in a jump-off,” says Robert. “Unfortunately, I had one down, but my round was very fast, and I think that that put a lot of pressure on Will.”

His cousin tried to repeat his clear first round while still maintaining a strong pace, and Robert had a nervous few minutes as Flamboyant III was clear right until the penultimate double of white gates. But when the second part of the double fell and William crossed the finish line 1.42sec slower, Robert had won the title.

He describes Gent, a son of Quick Easy 958, as a ‘big character’. “He’s very tough, and I think that's why he suits the Derby. We definitely fit each other, because from the start he was winning straight away. He's won so much for me, and he's got me back up the Rankings. It’s been a great partnership.”

He likes to get on with his work, but also he could buck you off at any minute.

At home, his groom, Harriet Keenleyside, describes the gelding as very chilled, very happy but very busy, always inquisitive and wanting to play with his stable toys. In the ring, he’s much more exuberant. “He's always quite fresh,” laughs Robert. “He likes to get on with his work, but also he could buck you off at any minute. I think that's a good thing for a horse of his age though, it shows he's happy and keen to get on with his job.”

As for this year, a decision has been made not to bring Gentlemen for another tilt at winning the Al Shira’aa Derby. He’s 20 now, still very fit, healthy and in excellent form, but having won the Derby last year it was felt the horse owed them nothing. Robert had always believed this horse could win the Hickstead Derby – and 12 months ago, Gentlemen proved him right. There can be few greater equine legacies than that.   

Robert’s win in 2025 made him and Dad John the first father and son to win the Hickstead Derby. Rob is also the fourth member of his famous family to lift the Boomerang Trophy, following in the footsteps of his Dad, Uncle Michael and his cousin William.  

Brothers John and Michael are among four riders to have completed four wins in Hickstead’s iconic class, a record that stood until 2024 when William Funnell won for a fifth time. Michael was the first of the siblings to win the class, taking the title in 1980 with Owen Gregory. John joined him on the roll of honour three years later, taking the 1983 renewal with Ryan’s Son. Michael then had a hat-trick of wins with the great Mon Santa, winning in 1991, 92 and 93. John won with the veterans Gammon and Welham in 1998 and 2000, before completing the four-timer in 2004 with catch ride Buddy Bunn, a horse belonging to Hickstead founder Douglas Bunn. 

William Whitaker became the third member of the Whitaker clan to win the Hickstead Derby back in 2016. Riding the chestnut Glenavadra Brilliant, he completed the course with all the fences left standing but picked up one time fault – fortunately for William, no other combinations jumped clear that year and he won the class.