Bren O’Brien



The Derby and Down Under: A Serpentine connection

2020 Derby winner Serpentine is set to become just the second winner in the English Classic’s 242-year history to race in Australia. Asian Racing Report takes a look at the connection between the Epsom feature and Australian racing.

Serpentine has already created his fair share of history, some of it desired, and some of it unwanted. On the good side, he romped to a dashing five-and-a-half-length all-the-way win under Emmet McNamara in the Derby at Epsom in 2020 in what was one of the more dominant wins in the famous race.

On the less-than-ideal side, it was a result achieved in front of no spectators, with the COVID pandemic preventing any meaningful attendance at Epsom, and the race held in July, a rarity, due to the delayed start to the racing season.

He has not greeted the judge in five starts since and in March it was confirmed that not only was he headed to Australia, with leviathan owner Lloyd Williams taking ownership, but that he would also become the first Derby winner in over 100 years to be gelded.


Serpentine and Emmet McNamara took out the 2020 Derby in dominant fashion. (Photo by BILL SELWYN/POOL/AFP via Getty Images)

It was quite the indignity for the son of Galileo who less than two years ago had led them a merry dance in one of the world’s most feted races, but perhaps also best understood in the context that he probably suffered for his exceptional pedigree.

There were 41 sons of Galileo standing at stud in Great Britain and Ireland in 2022, so the value of yet another one, even one with a Derby win on his resume, was less than the prospect of him racing on for Australia’s rich prizemoney.

On Saturday, almost two years to the day since his Derby success, Serpentine makes his first Australian appearance at Flemington. He will carry Williams’ iconic navy blue and white colours for trainer Robert Hickmott as top-weight in the Winter Championship Final over 1600 metres, looking to carve his own piece of history. 

He becomes what is believed to be just the second Derby winner to race in Australia. The first was also owned by Williams, Anthony Van Dyck. The first Derby winner bred out of an Australian mare, Believe’n’succeed, Anthony Van Dyck was another son of Galileo trained by Aidan O’Brien.

Anthony Van Dyck - out of a Blue Diamond Prelude-winning mare - staving off the challengers in the Epsom Derby of 2019. (Photo by Simon Cooper/PA Images via Getty Images)

His trip to Australia started out with such promise, a second in the Caulfield Cup, and ended in tragedy, with his much-publicised death in the 2020 Melbourne Cup.

Prior to that point, Australia’s major connection to the Epsom Derby was through its best jockeys experiencing success on the big stage at Epsom. Scobie Breasley famously won the Derby twice, in 1964 aboard Santa Claus and in 1966 aboard Charlottown. George Moore would follow suit the following year on Royal Palace in what was a golden era for Australian jockeys travelling overseas.

Further back, Australia’s greatest horse of the 19th century, the New Zealand-bred Carbine, who carried a record 66kg to win the 1890 Melbourne Cup, was the sire of the 1906 Derby winner, Spearmint.

There are also a couple of Derby winners named with a distinct connection to Australia. There is the 2014 winner (yet another for O’Brien), named Australia, while in 1853, a colt named West Australian won The Derby. He was by a sire named Melbourne.

From the breeding barn

In the shuttle stallion era, there have been a host of winners of The Derby who have found their way to breeding barns in Australia and New Zealand. 1990 winner Quest For Fame blazed a trail in that regard, first arriving in Australia in 1993 and spending much of his 17 seasons at Woodlands Stud. He produced Group 1 winners De Beers, Dracula, Perfect Partner, Sarrera, Tributes and Viscount.

Prior to that, Charlottown, Moore’s second Derby winner, had stood in Victoria late in his career, while 1937 winner Mid-Day Sun and 1991 winner Generous both stood in New Zealand.

Since then, the most influential Derby winners in terms of stallions in this part of the world have been Galileo and High Chaparral, who won the Epsom feature in 2001 and 2002 respectively.

The late great Galileo. (Photo by Coolmore)

Galileo has become the most successful global stallion of the 21st century but his five seasons shuttling to Coolmore Australia are largely seen as a missed opportunity. He would produce five Group One winners from those crops, Linton, Niwot and Sousa as well as South African stars Mahbooba and Igugu, and 28 stakes winners in total. Four of his Northern Hemisphere-bred progeny would also win Group One races in Australia.

While he died in 2021, his influence in Australia is massive. There are 20 stallions on Australian stud rosters in 2022 with Galileo in their pedigree, plus another eight in New Zealand. His daughters have produced nine Australian Group One winners to date.

High Chaparral’s influence has been arguably greater in this part of the world, certainly with his own progeny. He started out at Windsor Park Stud in New Zealand in 2005 and then stood for a further five seasons at Coolmore Australia from 2010. He had 16 stakes winners in Australia and seven in New Zealand from those crops. Among his Southern Hemisphere progeny are such stars as So You Think, Dundeel, Shoot Out, Descarado and Monaco Consul.

Leading sire So You Think. (Photo by Coolmore)

Having died in 2014, his legacy carries on through a host of sire sons, chiefly So You Think, Toronado and Dundeel.

Given those successes you would have thought Southern Hemisphere breeders would have been keen to punt again on Epsom Derby winners as shuttle prospects. But just three of the past 20 Derby winners have ended up in Australia as stallions, while two have travelled to New Zealand.

2007 winner Authorized spent four seasons shuttling to Darley’s Australian base and he was joined by 2008 victor New Approach, who also had four seasons there. 2012 winner Camelot was the last Derby winner to travel to Australia for stud duties, coming to Coolmore in 2014 for just one season.



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