Bootlegger

Image: Bootlegger pictured as a yearling, Credit Inglis

Some pedigrees are like a lone whistle, the hybrid vigour type coming out clear and clean. Others are more like a seven-part harmony.

For lovers of an intricate pedigree, that belonging to dual Adelaide stakes winner Bootlegger (Too Darn Hot) is what’s known in technical breeding terms as “a doozy”.

South Australian breeder Robert Hill-Smith and his advisor Damon Gabbedy decided to put the mare Princess Youmzain (Dalakhani) to an unproven second-season shuttler to Australia named Too Darn Hot (Dubawi), and like a golden run at the blackjack table, the cards all fell into place.

The result is that the pedigree of Bootlegger – a poster boy for South Australian breeding who claimed his second black type win with a tough all-the-way victory in Saturday’s Leon McDonald Stakes (Listed, 1400m) – is an intriguing one indeed.

Princess Youmzain did little elsewhere – she won one race over 1800 metres in Germany from four starts for Melbourne Cup (Gr 1, 3200m)-winning trained Andreas Wohler, and her other four foals of age have been moderate – but her mating with Too Darn Hot produced a lattice work of some beauty, especially now it’s been franked by Bootlegger’s performances.

There are four powerful duplications in key positions in the first five generations, strengthened further when you expand to six.

The first that stands out is Delsy (Abdos). Born in 1972, she was Group 3-placed in her native France but soared in the breeding barn.

She’s the dam of the outstanding Aga Khan-bred broodmare Darara (Top Ville), who won the Prix Vermeille (Gr 1, 2400m) and left no fewer than four categorised Champions and five Group 1 winners. Darara was bought by Lord and Lady Lloyd Webber of Watership Down Stud in 1994 for a hefty 470,000 Irish guineas, just short of $1 million Australian.

Among Darara’s progeny was Darazari (Sadler’s Wells), who won a Group 2 in France and came to Australia to win the 1999 Ranvet Stakes (Gr 1, 2000m) at Rosehill.

Darara also left Dar Re Mi (Singspiel), who for the Lloyd Webbers won three Group 1s in Ireland, England and Dubai. When she was covered by Dubawi (Dubai Millennium) – who like Dar Re Mi had top-tier winning parents – it resulted in another triple Group 1 winner, Too Darn Hot.

Delsy’s other star progeny was Darshaan (Shirley Heights), who won the Prix du Jockey Club (Gr 1, 2100m), for the Aga Khan. At stud his progeny included 2003 European Horse of the Year Dalakhani, who won four times at the top level before going to stud.

Dalakhani shuttled to today’s column’s neck of the woods – Cornerstone Stud in South Australia – for three seasons in the early 2010s. But back in Europe he sired the British-bred Princess Youmzain.

And thus Bootlegger has this great progenitor Delsy repeated in his pedigree at 4f x 4m in strong places – Too Darn Hot’s female line and Princess Youmzain’s paternal line.

Bootlegger is also powered by inbreeding to three key stallions – Sadler’s Wells (Northern Dancer), Shirley Heights (Mill Reef) and Mr. Prospector (Raise A Native), the last two of whom appear in triplicate within the first six columns.

Sadler’s Wells sits at 5m x 4f, as Dar Re Mi’s third sire (via his son In The Wings) and as the sire of Bootlegger’s third dam Wells Whisper.

Shirley Heights is at 5m, 6f x 4m, He’s the sire of Dubawi’s damsire, the damsire of In The Wings, and flows strongly into Princess Youmzain as her third sire.

And Mr. Prospector makes his presence felt in a 5m x 5m, 6m. He’s Too Darn Hot’s fourth sire and comes in twice in the bottom half since Princess Youmzain is inbred to his son Miswaki – Dalakhani’s damsire and the father of Bootlegger’s fourth dam Whakalyric. Showing the strength of his daughters, Miswaki is also the damsire of the great Galileo (Sadler’s Wells), although he’s not here.

There’s a few more duplications in the sixth column which can’t hurt.

Buckpasser (Tom Fool) is at 6f x 6f and appears five times in the first seven columns.

Lyphard (Northern Dancer) is at 6m x 6f, the latter as Bootlegger’s fifth damsire. The French stallion Herbager (Vandale) is at 6f x 6m, though somewhat buried, and appears four times overall in the first nine generations. And the great Northern Dancer (Nearctic) is at 6m, 6m x 6m, 5m amid six spots in total.

For good measure the influential mare Lalun (Djeddah) brings up the rear at 8m, 8m, 9m x 7m, 7m, while her fellow North American blue hen Natalma (Native Dancer) takes seven spots, six as Northern Dancer’s dam.

Overall, though, it’s that key repetition of Delsy that is strongly at play. She’s the highest contributor of blood to Bootlegger, with 12.5 per cent, ahead of Shirley Heights’ 10.94 per cent and the 9.38 per cent each from Sadler’s Wells, Miswaki and Northern Dancer.

While Princess Youmzain herself was no star on the racetrack, Bootlegger’s female line boasts a good dose of quality.

That third dam Wells Whisper threw two Listed winners in Germany, one of whom bore a German elite winner in Well Timed (Holy Roman Emperor), who took Dusseldorf’s Preis der Diana (Gr 1, 2200m).

And unraced second dam Wonder Why (Tiger Hill) threw two Group winners including Akeed Mofeed (Dubawi), who claimed the Hong Kong Cup (Gr 1, 2000m) and Hong Kong Derby (Listed, 2000m) amid four stakes wins. He was another stallion to stand at Cornerstone Stud for a time – among a few other farms in a modest breeding career to date. This South Australian proximity and familiarity helped influence Hill-Smith to buy Princess Youmzain, he says.

But while Bootlegger’s pedigree is laced with all of these juicy repetitions, they came about as something of a bonus. The main impetus was finding a stallion to suit Princess Youmzain on type.

She was bought out of Ireland by Cornerstone, continuing their association with Dalakhani, and later purchased privately from that farm by Hill-Smith, in-foal to Pierro (Lonhro). But until fifth foal Bootlegger she’d had precious little success at stud.

That Pierro filly – Clover Beat – at least fetched $100,000 when bought as a yearling by Busuttin Racing, but never saw a racetrack.

Hill-Smith, the owner of Yalumba Wines who breeds through his Vintage Bloodstock holdings, next bred Zain Prince (So You Think). Now seven, he’s won four times in the bush and once placed at Morphettville. Next came Hungry Guest (Merchant Navy), who was unplaced in five starts.

Almost despairing, in 2020 Hill-Smith sent his Princess Youmzain to Too Darn Hot, standing his first season in Australia at $44,000 (inc GST). The bad luck continued when she missed, but his second try a year later produced Bootlegger.

“To say Princess Youmzain was a bit disappointing as a broodmare is a bit of an understatement,” Hill-Smith tells It’s In The Blood.

“She had a helluva good pedigree. Dalakhani wasn’t the best, but he’s not a bad broodmare sire. And Akeed Mofeed was still producing winners when I bought her.

“I probably over-covered her, considering the performance of her produce, but

Too Darn Hot had a beautiful pedigree and I thought, ‘This is the last shot’.”

Gabbedy, of Belmont Bloodstock, was also keen on the mating.

“We liked Too Darn Hot’s credentials. We loved him as a sire prospect and loved the Dubawi sireline,” he tells It’s In The Blood.

“But most importantly, he was physically compatible for Princess Youmzain. She was a very tall, lanky, skinny mare. Her two foals prior to Bootlegger were like her – tall and lanky. We thought, ‘We’ve got to find a stallion who’s physically compatible for her’.

“Too Darn Hot was small-to-medium sized, chunky like a Not A Single Doubt type of stallion, and we thought that physical was the best that would suit her.

“That was the first criteria.”

Then Gabbedy and Hill-Smith explored what the pedigree would look like.

“And I thought – this is a really interesting pedigree, actually,” Gabbedy says.

“There’s a double of Mr. Prospector, a double of Shirley Heights, a double of Sadler’s Wells – and then you get inbred to Delsy.

“I couldn’t find many stats on inbreeding to Delsy, but a wise man once told me inbreeding to superior females is not a bad idea.

“So the double-ups looked appealing. Then we looked at Dubawi over Dalakhani as well. That hadn’t been done heaps but was showing some promising signs.”

Dubawi over Dalakhani is now more than promising. With four stakes winners from 11 runners at 36 per cent, it’s the legendary sire’s second-best nick of 11 runners or more.

Too Darn Hot over Dalakhani runs at 16 per cent, thanks to Bootlegger being among its three winners from six starters. But the Darley shuttler’s first Group 1 winner was Fallen Angel, who claimed Ireland’s Moyglare Stakes (Gr 1, 7f) and has Dalakhani as second damsire.

Gabbedy says the physicals at the top of Bootlegger’s pedigree offset any fears about possible stoutness in the foal.

“Shirley Heights has good inbreeding stats, and Mr. Prospector is a fantastic influence,” he said.

“You do have to be careful with doubling Sadler’s Wells, because you can get quite stout offspring. And Princess Youmzain’s damsire was Tiger Hills, by Danehill, which brings stoutness too.

“But Dubawi and Too Darn Hot were sort of more milers, so we were trying to get their physical into the mare. It’s really good when it works out alright.”

Bootlegger went to the 2024 Inglis Premier Yearling Sale but was passed in at $125,000.

Hill-Smith organised some friends to join him in the ownership, and now the Clarken-MacGillivray trained four-year-old gelding is rewarding them in spades, with Saturday’s win following on from his first stakes success in the Morphettville Guineas (Listed, 1600m) last autumn.

“He’s improved. He’s an honest horse,” says Hill-Smith, who also bred 2014 South Australian Derby (Gr 1, 2500m) winner Kushadasi (Choisir) and last autumn’s Auraria Stakes (Gr 3, 1800m) winner and Australasian Oaks (Gr 1, 2000m) runner-up Mating Call (Brazen Beau).

“When Bootlegger won his second race we got offered quite a lot of money from Hong Kong. But it’s hard to have a good horse and have some fun, so we decided to keep him, and I’m glad we did. Saturday’s win was at weight-for-age, so it was a very good performance.”

Somewhat ironically, Princess Youmzain was moved on before Bootlegger proved she could throw a good one. After she missed to Darley’s Victor Ludorum (Shamardal) in 2023, Hill-Smith sold her the following year for all of $600, carrying a colt by Dubious (Not A Single Doubt).

That two-year-old colt remains unnamed at this stage, and Princess Youmzain sadly died four months after his birth, aged 13.

But through that spicy mating with Too Darn Hot, the lanky British-bred mare has left a worthy legacy.