Trippi – The Tale Of A Titan Continues

A story of a champion

This week bloodstock expert Robin Bruss continues with part 2 of the story of champion Trippi and the Search for Greatness.

“Trippi has been a very special horse for us, and his influence on the stud is enormous.  He is probably the most important stallion acquisition that I have ever made” – Gaynor Rupert.

Drakenstein’s Foundation Sire Trippi (USA): Champion Sire, Sire of Sires, Sire of Champion Broodmares

In 2008, Gaynor Rupert had an important decision to make regarding the foundation sire for her Drakenstein Stud, her thoroughbred breeding farm established in 2003 on the very beautiful 3,200 acre L’Ormarins Wine Estate.

The land, known as L’Ormarins, was occupied from 1694 by French Huguenot, Jean Roi, who established the first 4000 vines. The farm was acquired by Anthonij Rupert with the vision to establish the finest wines in the country, but tragically, he lost his life in a car accident in 2001, and Johan continued the vision in honour of his late younger brother.

It was Johan that suggested to Gaynor that she bring her horses to L’Ormarins, located at the foot of the Drakenstein mountains near the picturesque village of Franschhoek and to use the high slopes adjacent to the famous vines.   Gaynor then nurtured her own vision: to breed quality racehorses both as a commercial venture and to enjoy the sport of racing for herself.

Studying some of the best stud farms around the world, the layout was spacious, and the design an architectural masterpiece on a scale befitting the joy of owning of a thing of great beauty.

Visitors have remarked that Drakenstein’s vista is one of the most beautiful on the planet.

Foundation Sire

By 2008, it was time to think about the acquisition of a foundation sire, a horse with speed and quality, and preferably, a stallion that had proven himself on the racecourse plus distinguished himself as a fertile sire of quality winners.

“It was Charles Faull of Form Bloodstock who did the research and provided me with a list of potential candidates” says Gaynor, “and I determined to travel to America to go and see them”

“Charles put me in touch with his American counterpart, Joe Brocklebank, and we began to go and see the horses one by one”.

“When I saw Trippi, I was instantly taken in by his great beauty, his quality and physical prowess, and he was easily the best horse that I had viewed and I was determined to make a successful offer to buy him”.

Apart from his race record, Trippi was rapidly gaining attention as the leading young sire in the state of Florida. He had sired 17 juvenile winners in his first crop racing in 2005, amongst them 3 Stakes Winners.

He had 5 SW in each of his second and third crop, and by the time Gaynor arrived in 2008, his first three crops had yielded 13 SW, although only 3 of these were graded stakes winners, and the best of them Miss Macy Sue, had won one Gr.3 and five listed races.

Michael O’Farrel of Ocala Stud said that selling Trippi was bitter sweet but two of the partners in the horse were dispersing and a third was reducing his stock – and Trippi’s sale had returned a handsome dividend on their investment.

Negotiation was quick and Trippi was purchased for  a significant sum and Gaynor had her proven sire around which to build Drakenstein Stud.

Syndication followed in South Africa, Drakenstein retaining half the horse and inviting other breeders to subscribe for shares.

The syndication was not without some difficulty as the exchange rate made the shares expensive in the South African market , and there was more than one complaint at the time about affordability.

However, when buying a stallion in 2008 that had commenced covering in 2002, there was the knowledge that Trippi had several crops in the pipeline in America and it didn’t take long for good news to flow from across the oceans.

In 2009, a Trippi filly called Jealous Cat (USA) emerged as blindingly fast in her first start over 900m.  The owners did something very unusual. They flew her across the Atlantic to Europe and ran her in the fastest juvenile race for fillies, the Queen Mary Stakes (Gr.2) at Royal Ascot, and she blitzed the best of the European generation at 5 furlongs to win easily.

R Heat Lightning (USA), another brilliant Trippi filly, emerged as one of the best of her generation in USA, winning the Spinaway S. (Gr.1) for 2 year olds at Saratoga and completed her juvenile season with an excellent 2nd in the Breeders Cup Juvenile Fillies S. (Gr.1), to rank #2 amongst all American juvenile fillies.

The 2007 and 2008 American crops yielded 9 SW each and a further 3 in the 2009 crop.  In 2009, Trippi was the #1 Leading Sire in Florida, #1 Leading Sire of 2 Year Olds in Florida, and #3 Leading Third Crop sire in America, with 75% winners, and progeny earnings of $16 million.  His American yearlings were selling for up to US$450,000.

Ultimately Trippi’s 7 American crops ended up yielding no less than 33 Stakes Winners who won 72 Stakes Races.

It was pretty obvious that Trippi’s acquisition was a brilliant buy with fortuitous timing – a season or two later and he would have been double or triple the price and almost certainly would not have arrived in South Africa.

“I was very, very lucky with Trippi” said Gaynor, “when I saw him, he was the most beautiful horse, I fell in love with him and my instinct was that I just knew that he would be very successful for us – and that is how it has turned out to be.”

Trippi in South Africa

 Trippi’s first South African Crop was bred on a service fee of R100 000, with Western Winter (R200 000), Jet Master (R170 000) and Fort Wood (R150 000) standing for higher fees.

Trippi’s first crop of runners made him Champion First crop Sire and his career started well, but it wasn’t until this second SA crop that he sired his first South African Grade 1 winner when Klawervlei bred For the Lads who won the Gr.1 Golden Slipper. The third crop was the ‘tour de force’ :  here were FOUR Gr.1 winners in the crop and the first South African Champion.

Drakenstein bred and raced Inara (out of Mountains of Mist IRE, by Derby winner Shirley Heights) added stamina to Trippi’s speed, and Inara won 5 Gr.1 events from 1200m to 1800m – she won the Majorca S. Gr.1 twice, the Empress Club S. Gr.1 and the Garden Province S. Gr.1, and the Paddock S. Gr.1, traversing all three major provinces and became Equus Champion Filly.

Drakenstein bred and owned Champion Inara (by Trippi) won 5 Gr.1 races

Drakenstein foaled and raised, Deo Juvente won the R3,5m Champions Challenge Gr.1 over 2000m, Afrikaburn won the Golden Horseshoe Gr.1 and Maine Chance bred Real Princess won the SA Fillies Sprint Gr.1.

Eight Gr.1 wins in a short space of time and Trippi deservedly became  Champion Sire in 2015.

“It hasn’t been a surprise for us that Trippi ended up being Champion Sire” said Drakenstein’s Manager, Kevin Sommerville, “and we are super proud of him and his achievements. A lot of owners and trainers always thought that Trippi could not become Champion Sire because he was so fast that he would not sire winners at 2000m. or more where most of the big prize money is concentrated. But he has succeeded in siring winners over all distances”

In fact, Trippi in his total career has sired 830 individual winners who have won 2,813 races and these range from 800m to 2500m+.

He is also a very versatile stallion on any racing surface and he has Graded SW in dirt and turf and polytrack and on all types of going, although they love the firm ground of South African tracks.

“One of the hardest things to find in breeding,” observes Kevin, “is to find a stallion that’s ultra consistent and predictable and it makes them very easy to work with.  Trippi is that stallion and he is one of the best I have ever seen”.

“Trippi foals are independent, they have strong minds, they don’t like to be forced to do what they don’t want to do, so in the hands of patient trainers, who don’t get too hard on their horse, Trippi progeny thrive. They are very, very genuine horses, both colts and fillies, but you have to give them the chance to be genuine”.

The 2014 crop yielded SA Classic Gr.1 winner Lobo’s Legend, bred by Klawervlei and in 2015 Drakenstein bred Chimichuri Run emerged as a top class sprinter winning 8 races including the Tsogo Sun Sprint Gr.1 and R2,2 million, earning a reputation for toughness and soundness.

He now stands as a stallion at Blue Sky Thoroughbreds in KZN.

Trippi’s son Chimichuri Run (Pic – Candiese Lenferna)

Trippi’s first Horse of the Year Jet Dark was born in the 2017 crop.

Kevin remembers him as a tall and lanky yearling with great scope, but very immature at the National Yearling Sales, where he sold for R200,000 to the bid of Nic Jonsson, an exceptional buy as Jet Dark went on to win five Gr.1 races including the L’Ormarins Queens Plate Gr.1 twice, the Cape Met Gr.1, the Champions Cup Gr.1 twice, and was 2nd in the July Gr.1

He was Equus Horse of the Year and in 2023 he retired back to the home of his birth to stand as the most popular first crop sire attracting 134 mares at a fee of R30,000.

The exceptionally good looking Jet Dark is out of a Jet Master mare and inherited more size and scope than the regular Trippi – and more stamina.

It’s interesting that Jet Master mares sent to Trippi produced 28 runners and 25 of them (90%) were winners, and three were SW.

Jet Dark wins the L’Ormarins Queen’s Plate Gr.1 (1600m) for the second time.

The stellar year enjoyed by Trippi in 2023 was really all about the stellar year enjoyed by Drakenstein, now come of age as a mature farm with a steady stream of high class runners, good sales results and great homebred results.

“I have had great luck” says Gaynor “because I retained Sweet Pepper as a future broodmare and she won the Allan Robertson Fillies Championship Gr.1, Trip of Fortune didn’t make his reserve at the yearling sales and so I raced him, Charles Dickens couldn’t go to the sale because it was thought he had a soft palate issue,  and Winchester Mansion broke a bone in his neck as a weanling and I could not sell him”

In the rollercoaster of horseracing, somehow it’s often what appears to be the bad news, that ends up as the most fortuitous.

Winchester Mansion’s victory in the 2023 Hollywoodbets July Gr.1 was Trippi’s first Gr.1 win at 2200m and in South Africa’s most prestigious race.

Trip of Fortune won the 2023 Horse Chestnut S. Gr.1 at 1600m and Charles Dickens became the best horse owned and bred by Drakenstein to date, with 10 wins in 13 starts, over R5m in earnings.

All three earned Equus Awards in 2023 and were major contributors to the exceptional achievement for Drakenstein to become both Champion Owner and Champion Breeder in the same season, a feat that I believe was only accomplished once before – by Graham Beck.

Of the 13 individual winners produced by Trippi, one was un USA and 12 in South Africa.  Of these 9 (or 75%) were bred and foaled at Drakenstein, two came from Klawervlei, and one from Maine Chance.

Of the 13, four have inbreeding to Mr Prospector within 4 generations, the rest are essentially outcrossed matings, so Trippi suited a very wide variety of mares.  Almost all have inbreedings to Northern Dancer further back but that’s almost impossible to avoid these days.

The highest percentage of stakes winners belong to the cross between Trippi and SA bred Dynasty, with 10 runners, 8 winners (80% winners) and 4 of the 8 winners becoming stakes winners, amongst them the brilliant Charles Dickens.

Charles Dicken’s incredible victory in the L’Omarins Kings Plate Gr.1 on 6 January sealed Trippi’s career with an incredible champion as Trippi, now 27 years old comes to the end of his reign, with Charles Dickens and Jet Dark stepping up to assume the mantle as sons of the King and Lords of Drakenstein.

It’s hard not to quote from namesake Charles Dickens  in the unfolding story of what has happened.

“They are the future of Drakenstein Stud” says Gaynor, without omitting the 30 odd daughters of Trippi on the farm, most of them stakes winners.

Kevin Sommerville and Gaynor Rupert lead in the magnificent Charles Dickens following his victory in the Hollywoodbets Gr1 Cape Guineas

From chaos comes order, from opportunity comes enterprise, from immaturity comes maturity, and in the roller coaster of horse breeding and racing, Drakenstein first phase has been cemented by the steadiness of a great foundation stallion.

Finding outcrosses for Trippi’s sons and daughters becomes the next step for the potential growth of the farm, bit that’s all for discussion in a future chapter of the story.

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