DRAKENSTEIN STUD | PRESS RELEASE
TRIPPI: Champion sire and foundation stallion of Drakenstein Stud dies aged 29
FRANSCHHOEK, 27 August 2026 – It is with immense sadness that Drakenstein Stud announces the passing of Champion sire and Equus Outstanding sire Trippi. The American-bred son of End Sweep, whose stud career linked Ocala, Florida, and South Africa, helped to shape Drakenstein Stud.
After establishing the Stud in 2003, Gaynor Rupert travelled to America to view 28 potential stallions, and was immediately captivated by the magnificent bay, describing him as the most beautiful horse she had ever seen. Gaynor made the decision to purchase him as her first sire to stand at Drakenstein, and the beginning of a legacy was born. He travelled to South Africa after the 2008 northern-hemisphere breeding season, where he became the foundation sire of a stallion operation that has since established itself as one of the country’s principal nurseries.
Foaled in Florida in 1997, Trippi was bred by Harry T. Mangurian, Jr. and raced for Dogwood Stable under Todd Pletcher. He won seven of his 14 starts, headed by the Grade 1 Vosburgh Stakes, with further graded victories in the Riva Ridge Stakes, Tom Fool Handicap, Flamingo Stakes, and Swale Stakes. He then stood at Ocala Stud, where his American crops established him among Florida’s leading sires before his move to Drakenstein.
The change of hemisphere did not narrow his influence. Trippi supplied speed, precocity, and, often, the ability to carry that speed beyond sprint distances. He was South Africa’s champion sire in 2015/16 and, from 1,073 runners worldwide, sired 857 winners, including 94 stakes winners of 191 stakes races. His record includes 14 individual Grade 1 winners.
His South African record was led by two champions now standing alongside his legacy at Drakenstein. Charles Dickens, winner of the Cape Guineas, Gold Challenge, and King’s Plate, was a miler of remarkable acceleration and consistency. Jet Dark won five Grade 1 races, including two Queen’s Plates, two Champions Cups, and the Cape Town Met, and was effective from a mile to 2,000 metres. Both have retired to stud, giving Trippi a direct route into the next generation of South African pedigrees.
There was immense depth behind them. Winchester Mansion won the 2023 Durban July, while Trippi’s other South African Grade 1 winners included Afrikaburn, Deo Juvente, Inara, October Morn, Real Princess, Chimichuri Run, Lobo’s Legend, For The Lads, Sweet Pepper and Trip Of Fortune. His better runners ranged from early two-year-olds to older horses, and from fast-track performers to horses capable of succeeding in South Africa’s foremost middle-distance races.
His American legacy has proved equally durable through his daughters. Miss Macy Sue, one of his early US-bred stakes winners, produced Liam’s Map and Not This Time. Liam’s Map won the Grade 1 Woodward Stakes and Breeders’ Cup Dirt Mile before becoming an established Kentucky stallion. Not This Time, runner-up in the Breeders’ Cup Juvenile, has developed into a leading sire in the United States, standing at $250,000 this season. Their successes have given Trippi an international influence as a broodmare sire beyond the achievements recorded in his own name.
In South Africa, too, his daughters have become a significant part of the broodmare population. As a broodmare sire of 66 stakes winners, including 9 Grade 1 winners, he’s continued to produce leading runners, reinforcing the qualities for which he became known. The value of that female line, together with the stud careers of Charles Dickens and Jet Dark, means his contribution will continue on more than one branch.
For Gaynor Rupert, Trippi’s importance was inseparable from the development of Drakenstein itself. He arrived before the farm had an established stallion roster and supplied it with an identity: an internationally proven horse whose results justified the decision to bring him to the Cape. Many of his best South African horses were bred or raced by Drakenstein, among them Charles Dickens, Inara, Winchester Mansion, and Trip Of Fortune, making his story inextricably bound to the farm’s own.
Trippi’s final crop are three-year-olds in South Africa this season. As they continue to race, and as his sons’ first generations come through, the influence of Drakenstein’s first stallion remains very much a part of the present rather than only its history.
Trippi was expertly cared for by his long-time stallion handler Schedrick Oerson, whose favourite moments with Trippi were their daily walks on the farm in the mornings, just the two of them, like old friends. Schedrick shared that it was a privilege and an honour to work with him.
