Whatever Bootlegger does in the South Australia Sires’ Produce Stakes, the unexpected challenges of breeding racehorses will never be lost on prominent Adelaide businessman Robert Hill-Smith.
As the chairman of Yalumba, one of Australia’s foremost wineries, Hill-Smith also dabbles in thoroughbreds as part of another longstanding family tradition.
His father Wyndham was synonymous with racing in South Australia, playing a significant role in the establishment of Lindsay Park as a financial backer of the vision of the legendary trainer Colin Hayes.
The Hill-Smith Stakes, an Adelaide race programmed for early-season three-year-olds with Victoria Derby ambitions on their agenda, stands as a permanent reminder of his influence on racing in the state.
Hill-Smith’s thoroughbred interests have never matched the scale of his father’s investment but they have been enough to experience the peaks and troughs that accompany the bloodstock industry.
Bootlegger, a two-year-old of genuine promise with a win and a placing from two starts and is rated among the better chances in the Sires’, is a perfect example.
It’s an end-of-season twist to Hill-Smith’s racing fortunes after the premature retirement of his stakes placegetter Thirsty Guest as well as a reward for staying the distance with a horse bred from a mare that he described as a “disappointment” before her death last year.
As a son of Darley’s exceptional sire Too Darn Hot, Bootlegger was catalogued for last year’s Melbourne Premier Yearling Sale.
The Australian first-season progeny of Too Darn Hot were up and about and Hill-Smith placed what he thought was a fair reserve on the colt.
There was nothing discreet about Bootlegger’s win!
— Dare To Dream (@DareToDreamSA) July 7, 2025
The 2YO was very impressive winning his maiden at Gawler. https://t.co/KedH1SUEn0 pic.twitter.com/LY2RrjQGoa
Alas, bidding stalled well below expectations and the colt out of the Dalakhani mare Princess Youmzain was passed in well short of the $150,000 Hill-Smith wanted.
“He didn't get into that space. I don't know why because we had a lot of people look at him and like him,” Hill-Smith told The Straight.
“The vet X-rays were fine, but on the day no one turned up for whatever reason.
“It was a bit of a dull spot in the sale to be honest … and sometimes you get those, if for no reason at all you end up in that spot.
“So we struck out sadly, but I liked him and decided to keep him and take the risk before I sold half of him to mates of mine who all love their racing.”
Princess Youmzain, a half-sister to Hong Kong star Akeed Mofeed, who coincidentally enough stood at the old Lindsay Park earlier in his career, was sourced out of the UK. She was on-sold by Vintage Thoroughbreds on Inglis Digital last year.
From the stable of Dan Clarken and Oopy MacGillivray, the co-trainers who took The Map to last year’s Melbourne Cup, Bootlegger made a late-season debut with a placing last month that was parlayed into a Gawler win and subsequent overseas interest.
For the second time, it wasn’t enough for Hill-Smith to consider selling.
“I've had an offer from Hong Kong for him, but we’ve decided at this point to race the horse rather than make the money,” he said.
“We're in it for fun now and not for money. So that's where it's going to finish here with us.”
The Sires’ figured in a move in 2024 as a Group 3 finale to two-year-old stakes racing in Australia for the season.
Its switch from a supporting race during the Adelaide carnival in April and May has been designed to give latecomers in the juvenile ranks an opportunity to showcase what they might have to offer as next season's three-year-olds.
It has attracted entries from leading Victorian stables, including Ciaron Maher, Tony and Calvin McEvoy, and Lindsay Park.
Hill-Smith says untapped youngsters such as the McEvoys’ unbeaten Volkano, another son of Too Darn Hot who is disputing Sires’ favouritism with Bootlegger, will provide an insight into the future.
“Bootlegger is an animal that hasn’t really furnished in my view. He’s done well to do what he’s already done,” Hill-Smith said.
“Hopefully, over the next 18 months he can come into his own.
“It's not an easy field but I hope he runs up to his talent, and at least we'll get a handle on what his ability is around slightly better horses.”
