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Daughter of legendary jockey flies to US in chase to win ‘world’s most expensive trophy’ with its own armed guard

Published on May 08, 2025 at 10:24 AM

SAFFIE OSBORNE – the daughter of legendary jockey and trainer Jamie Osborne – will fly to the US in the chase to win the ‘world’s most expensive trophy’.

Osborne confirmed Saffie will ride their stable star Heart Of Honour in next Saturday’s Preakness Stakes.

Woman smiling at a restaurant table.
Saffie Osborne, daughter of legendary jockey and top trainer Jamie, will ride their stable star Heart Of Honour in the Preakness Stakes, one of America’s biggest races and the middle leg of the Triple Crown
The Woodlawn Vase trophy at the 148th Preakness Stakes.
The Woodlawn Vase, said to be the world’s most expensive trophy, has its own armed guards when it makes a rare appearance in public for the Preakness
Trainer Jamie Osborne at a horse race.
Trainer Jamie Osborne is gunning for the biggest win of his life in the iconic US contest

The blockbuster American race is the second leg of the famous Triple Crown and famed for the Woodlawn Vase.

Tiffany and Co listed the trophy as officially priceless – while a valuation for insurance purposes said it was worth an amazing £3million.

The Woodlawn Vase lives in its own protective case throughout the year, until it is transported to Pimlico Racecourse in Baltimore, Maryland, by its own squad of armed guards on raceday.

The 30lb trophy stands 36 inches high and is constructed entirely of solid sterling silver.

It is so sought-after that even the winner of the race only gets a £30,000 replica.

The original Woodlawn Vase – which some dispute is actually second on the rich list behind the World Cup – remains behind a screen as the winning trainer hoists the smaller mini-me, which they get to keep forever.

Osborne, 57, who was leading jockey at the 1992 Cheltenham Festival, has his sights set on glory with their globe-trotting Heart Of Honour.

And he is relying on talented daughter Saffie – who made history by becoming the first woman jockey ever to ride a winner at Meydan in Dubai after – to get the job done.

Saffie, who has , and Heart Of Honour came close to a £500,000 payday in the UAE Derby last month.

The 3-1 joint-fav was nutted right on the line by a nose to 11-1 Admire Daytona in the money-spinning Grade 2.

Prior to that, the three-year-old colt was beaten just a head in a Listed Meydan race worth £100,000 to the winner.

Heart Of Honour has amassed prize money earnings of more than £270,000 from just six career runs.

Not bad at all for a horse who finished second on his debut at Southwell in October last year having been sent off 22-1.

Speaking of his decision to send Heart Of Honour to the States, Osborne said: “We thought this was worth a shot.

“He’s only three once. There’s nothing in the UK for him.

“So, the alternative was to give him a break, a long-extended break, and wait for next year’s Middle East season when we go back to Dubai.

“The Kentucky Derby was clearly going to be too soon for him.

“Logistically, it was going to be nearly impossible to ship from Dubai back here and then to America.

“The extra couple of weeks will probably be to our benefit, as well.

“We’re going to have a go, and if he runs OK in the Preakness, the aim is to hang on for another three weeks and go to Saratoga.

“I think this horse, in what he’s achieved so far, has to step up, but I think there’s a chance that he can step up.

“He’s a horse that seems to be maturing and coming around this time of year.”;

Victory would be a monumental family achievement for the Osbornes.

Saffie has carried the family name with total class during her years as a top performer on the Flat.

A true globe-trotting star, she’s won multiple times at Group level, including most recently in Doha aboard fan favourite Emaraaty Ana.


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