The silhouette is instantly familiar as he opens the gate at his Exning property, on the fringe of Newmarket. The pencil-thin legs decked in perfectly-fitting denim; the quick, shuffling gait as he marches along with purpose; and the beaming smile. The only thing different about Darryll ‘Dazzler’ Holland is that his jet-black hair is flecked with grey.
Holland has always radiated a sense of contentment, and he does so now. The child-prodigy rider once tipped for absolute stardom is back in Britain, plainly excited by his appointment as stable jockey to Charlie Hills. Following recent stints in South Korea and Mauritius, it is a home-coming in more ways than one.
“The other day I had a chat with Frankie [Dettori], who is one year older than me,” Holland reflects. “He has gone back to his roots with John Gosden and I’m in the same scenario. It’s a great feeling for both of us.”
Holland’s association with the Hills family dates back to 1988, when the Manchester-born wannabe went to work for Charlie’s father, Barry, in Lambourn. “I was 15 at the time and Charlie was eight or nine,” he says. “We were brought along together, running around the yard with Mrs [Penny] Hills telling us off all the time.”
That was almost 30 years ago, since when Holland, 43, has become one of the world’s most travelled jockeys.
It does niggle me that I’ve never been champion. It niggled Richard Hughes a lot until he was champion late in his career, so nothing’s impossible
In 1994 he became the youngest foreign import into the competitive jockeys’ colony in Hong Kong. He subsequently rode in Japan and Singapore during the off-season before returning home to consolidate his place among the top five riders in Britain. He earned a lot of money but his resume is bereft of a British Classic winner.
From a conventional perspective, this is a glaring anomaly for one of his talent. But Holland has never been beholden to convention, both in and out of the saddle. Geography was his strongest subject at school, where he was seen as brighter than average. It infused him with a spirit of adventure.
To this day Barry Hills maintains Holland had as much natural prowess as any young aspirant to pass through his hands. “Darryll had never sat on a horse before he came to the yard but he was riding within a few months,” Hills told me back in 2007. “It took him about two minutes to discover he was good. He should have been champion jockey.”
It’s a lament Holland shares, although it wasn’t for the wont of trying. He came closest in 2003 when he rode 157 winners, although at that time Kieren Fallon was in a league of his own. Two years later Fallon moved to Ireland to ride for Ballydoyle but a spate of falls, coupled with Holland’s late return from foreign assignments, saw the opportunity go begging.
“It does niggle me that I’ve never been champion,” Holland reflects. “It niggled Richard Hughes a lot until he was champion late in his career, so nothing’s impossible. But that is not my priority right now. I’ve got to concentrate on Charlie’s horses. He has nearly 200, which is a lot for me to get to know.”
In his pomp Holland was renowned for expressing forthright views. He was probably too honest for his own good. He’d hold his hand up when things went wrong where others would have spuriously deflected blame.
In 2003 he forged a fabulous relationship with Falbrav, a globetrotting bull of a horse who won five Group 1 races that season. But when Holland just failed to deliver Falbrav in the Irish Champion Stakes after a troubled passage, he did not go to ground.
Three weeks later he discussed every nuance of that race with a posse of journalists ahead of Falbrav’s bid for the Queen Elizabeth II Stakes – which he promptly went out and won. Nor does he shy away from some of the less flattering assessments on his career.
To the charge that he has underachieved, he replies: “I don’t think so. I have won plenty of Group 1 races in Britain, far more than most. I don’t think I’ve had a fall from grace or anything like that.”
Yes, there were times in a gilded youth when he did things he would regret. A sizeable entourage attached itself to him after he rode out his claim within 12 calendar months in 1991, when he broke the post-war record for apprentice-ridden winners. “Dealing with the hangers-on was the most difficult part,” he reflects now.
And he still winces about the time he went to Sweden to ride, joined local jockeys for an evening knees-up and failed the breathalyser at the racecourse the following morning.
“I had no idea I’d be breath-tested,” he says with a rueful smile. “Funnily enough, most of the jocks I’d been out with got tested too, but I was the only one to fail…”
I missed out on things like taking a year out after leaving school. I never had a proper girlfriend either, because I was too caught up in becoming a jockey
As conversation unfolds it becomes apparent Holland uses a different gauge to measure his professional achievements.
“I missed out on things like taking a year out after leaving school,” he says. “I never had a proper girlfriend either, because I was too caught up in becoming a jockey.
“So when I realised I could travel with my saddle, it really appealed. Some of the jobs I’ve had have been lucrative but it was more than that. I like meeting different people and doing different things. I’ve been lucky enough to be able to take my trade to different countries, which isn’t true of most jobs.”
Hence the lure to Holland of riding in South Korea, where he emigrated in 2014. “Some people thought it was a step down for me but I never saw it that way,” he says.
“It was another opportunity. I was the first European jockey to be licenced there and I had no ties at home. I’d just gone through a divorce and I’d been driving up and down the country without any decent rides. I also hoped it might rekindle something in me. I wasn’t enjoying it any more in the UK.”
Holland has always loved far-eastern food but the Korean racing experience was formative, not least in the way he had to fight to win local confidences. “I rode two winners on my first day but for six weeks after that I could hardly buy a ride to save my life,” he reflects.
“It was hard at first. I’d try and communicate with the boys in the weighing room. They’d all wave to me when I went in, but only one of them could speak broken English. They’d never ridden with a European rider and my style was very different.
“I think it was as much of a shock to them as it was to me. But I was determined I wouldn’t leave until I’d made it work. It would have been easy to throw in the towel. I stuck it out, and I’m glad I did. I always believed I’d come through.”
By the time Holland left, having renewed his contract twice, he’d long since earned the respect of South Korea’s racing community. He bowed out on a winner, too: his 65th from some 350 rides. From there, he made his way to Mauritius for four months before returning home in December.
The call from Charlie Hills came out of the blue.
When Charlie asked me to ride for him I went a bit silent. I’m not normally stuck for words but as soon as I could speak I said yes
“He rang me four days before Christmas,” Holland recalls. “I thought he was going to ask about the kids [Holland has 18-month-old twins]. When he asked me to ride for him I went a bit silent. I’m not normally stuck for words but as soon as I could speak I said yes.”
For Holland, it was exciting and reassuring to walk into Hills’s Faringdon Place stables. The herd of well-bred juveniles put a skip in his step, while a slew of familiar faces dating back to Barry’s days made him feel at home.
The new alliance was anointed on February 19 at Lingfield, when Holland rode Carry Me Home into third place. It was a low-key occasion at a venue a world away from the big summer racing festivals the pair have trained their sights on. Before that, however, Holland must regain his bearings.
“When I walked into the weighing room I soon realised I didn’t know anybody – and I don’t think many of them knew who I was, either,” he says.
“A couple of the lads said hello but I didn’t recognise them. I had the Racing Post open and was peering over the top of it to see which silks they were wearing, trying to find out who they were!”
Holland feels he has four or five good years left in him. He wants to spend them with Hills before he will likely try his hand at training. He has no regrets, says he wouldn’t want to change much even if he could, but would like to address the absence of a British Classic from his CV.
His biggest asset now is his experience. “You can’t buy it,” he says, “and I have a lot of it. A small mistake here and there makes the difference between winning and losing, so I have to make it count. I really want to make the most of the next few years. I feel I’ve still got a bit to offer in the saddle.”
It will be good to see this endearing character back on the stage he all but made his own two decades ago. Even his sponsor – former jockey-turned-author Barry Morgan, who has just penned his debut novel, Gift Horse – could not have scripted a better closing chapter for him.
Just when the story seemed told, Holland has a new focus, a new vigour, a new job, and an old ally to help him ride off into the sunset.
Racing’s odd couple: Darryll Holland and Matt Chapman
It was testament to Darryll Holland’s individualistic approach when he appointed Matt Chapman as his agent in 2002. At the time Chapman, a former Racing Post journalist, was forging a reputation as one of Britain’s premier racing presenters on television. The four-year association between two strong-willed people generated endless highs and lows.
“We’re still mates,” Holland says. “We’ll still meet for a pint but basically, Matt is as mad as a hatter. He was new to being a jockey’s agent but was very committed and turned his hand to it pretty quickly.”
On his appointment Chapman moved to Newmarket, where he and Holland had some epic jousts on the Play Station game, G1 Jockey. “If Matt ever won, which was extremely rare, I’d never live it down,” Holland reflects.
Needless to say, Chapman remembers it differently. “Darryll usually won but he’d get totally neurotic when he didn’t,” he says. “Whenever I won, he’d make me play again straight away so he could take his revenge.
“It was the same when we played tennis in Barbados,” Chapman continues. “I’d get ahead early and win a couple of sets, but he was fitter than me. He wouldn’t stop until he got ahead in sets, so he would often win 6-5 after four hours. He also kept trying to kill me whenever we went riding on jet-skis.”
Holland credits Chapman for getting him the prized mount aboard Falbrav and the new combination clicked at the first attempt in the 2003 Eclipse Stakes. “Matt is very pushy; he’s got that sort of character,” the jockey says. “He must have kept on at Luca [Cumani, Falbrav’s trainer] until he gave in. It also helped that Matt likes money.”
That was a flavour agreeable to both parties, according to Chapman. “Darryll used to call me ‘Jerry’, after [the character played by Tom Cruise in] the film Jerry Maguire. Every morning he’d shout at me, ‘Jerry, show me the money!’”
As for Falbrav, Chapman says: “In those days, if Kieren Fallon wasn’t available Darryll was the next go-to jockey. His standing was that high. As a team we had some huge highs and lows, but ‘Dazzler’ was always straightforward.
“Most people thought he was one of the best – if not the best – front-running jockey around. Yet when I look back, two of his finest winning rides were on Continent in the  July Cup and Just James in a Newmarket handicap [also 2002] that won him a Lester for Best Flat Ride of the Year. Both of those were habitual hold-up horses.”