THE prestige of the Epsom Derby is such that Jamie Osborne would probably trade many of his 11 wins at the Cheltenham Festival in return for Toast of New York, the horse of his dreams, winning Flat racing’s most celebrated contest next month.
It is also not wishful thinking on the part of the Hull-born horseman who grew up near Wetherby and became one of the country’s most stylish – and successful – jump jockeys with nearly 1,000 winners to his name before making the transition to the training ranks where successes have been more elusive and hard-earned.
One of 27 contenders left in the Investec Derby field, his horse is already a Classic winner after winning the UAE Derby on Dubai World Cup night in spectacular style and vindicating Osborne’s faith when he first spotted the colt’s potential.
Spurned by many, Osborne, 46, then had to turn on his famous charm to persuade leading National Hunt owner Michael Buckley to broaden his horizons and purchase a Flat horse Their only disagreement appears to be the name – Buckley called the horse Toast of New York in honour of a 1937 movie about a pair of rogue financiers in the Big Apple which starred Cary Grant after rejecting Osborne’s suggestion of The Smiling Assassin.
But this is a script that could still have a Hollywood ending after the horse began his career by winning two modest races at unfashionable Wolverhampton before winning the UAE Derby under Jamie Spencer.
With Spencer set to be claimed by Qatar Racing to ride Dante second Arod at Epsom, the likes of Frankie Dettori, Richard Hughes and Adam Kirby are in contention for the ride as Osborne seeks a career-changing moment in his seemingly endless quest to attract more horses and owners to his Lambourn yard.
“I have 50 horses. It’s not enough. A million is a sensible number. I want more,” he says.
Proud of his Yorkshire roots – Osborne hails from a hunting family, went to school in Boston Spa near Wetherby and served his racing apprenticeship with the likes of Neville Crump and Harry Wharton in Middleham before joining the yards of Nicky Henderson and then Oliver Sherwood – he is keen to build on his eight wins from 70 runners this season.
“Training a Derby horse, it’s something I’ve not done before but it is something that any trainer hopes to do at some stage,” Osborne told The Yorkshire Post.
“We’re very lucky to have a horse that is this good – I just hope it isn’t my one and only shout in the race. There are a lot of owners, and trainers, who are not in this position.
“There is a big element of chance in getting a horse like this. I bought him as a yearling at the Goffs sale in Ireland. He wasn’t everyone’s cup of tea – it took me six months to find a buyer and he has four white socks – but he was amazing when I saw him moving, even though he was a bit raw and a bit backward.
“If you had told me he would win a $2m race in the early part of the year as a three-year-old, and hold a Derby entry, I would have thought it highly unlikely. There were people who rejected him who are regretting it now.”
Despite being one of racing’s eternal optimists, Osborne still smokes to calm his nerves and has even taken the precaution of installing a CCTV camera in Toast of New York’s stable.
“It is to satisfy my paranoia that if anything happened to him in the middle of the night we have got it recorded,” he said.
“He is very important to us. All I will probably be seeing is a lot of sleeping because he does a lot of that.”
This insight reveals much about the trainer’s determination to join his sport’s elite since taking out a Flat licence at the turn of the century. Four Royal Ascot successes to date, and a Yorkshire Cup triumph with Geordieland in 2008, is a modest return for a man who rode five winners at the 1992 Cheltenham Festival, including an opening-day treble and a Queen Mother Champion Chase on the brilliant Remittance Man.
He thinks the term racehorse trainer is something of a misnomer.
“It conjures up images of horses jumping through hoops,” he says.
“We are the manager of a horse’s career. As his career manager, I felt Toast was too raw to compete at the top as a two-year-old.
“I used the smaller races at Wolverhampton to bring him on, show him off and get a high enough rating so we could get to Meydan.
“If he had not had these races, he might not have made the cut.
“In the UAE Derby, I didn’t think we had a horse that was better than any of the Godolphin three-year-olds and I would have taken third, but he bolted up and it was a great thrill.
“Training is different to riding. If one got beaten as a jockey, the next big race could come along in half an hour – or the next week.
“When training, good horses don’t come along that regularly. There are more disappointments than you get as a jockey.
“You can look good for entering a horse in a certain race or you can look a complete idiot depending on the outcome.”
As for the Epsom Derby, Osborne hopes for Toast of New York’s favoured dry ground so he can race handily and have every chance of staying the one-and-a-half-mile trip. If he does, it will not just be the horse who is the toast of racing.
So, too, will his trainer who hopes that his most successful days still lie ahead.