Jamie Osborne has been training in Upper Lambourn, near Hungerford, Berkshire since 2000 but, in his younger days, was a confident, even cocksure, National Hunt jockey. He earned the derogatory nickname “Pompous Pilot” and was famously slapped in the face by Jenny Pitman after deliberately hampering her horse Run To Form in a novices’ hurdle at Ayr in 1990. Nevertheless, he rode nearly 1,000 winners – including 12 at the Cheltenham Festival – for the likes of Nicky Henderson, Oliver Sherwood, Charlie Egerton and Henrietta Knight.
His new career started brightly, too, with 10 winners in 2000, rising to 31 in 2001, the year in which he saddled his first Royal Ascot winner, Irony, ridden by the late Pat Eddery, in the Coventry Stakes. Osborne has subsequently trained three more, Drawnfromthepast in the Windsor Castle Stakes and Enjoy The Moment in the Queen Alexandra Stakes in 2007 and Field Of Dream in the Royal Hunt Cup in 2014.
In 2002, Osborne was fined £4,000 by the Jockey Club after admitting bringing racing into disrepute by making unguarded remarks to Paul Kenyon, an undercover reporter for the BBC. Osborne was secretly filmed saying, “We’ll cheat. We don’t mind cheating”, but insisted the remarks were taken out of context.
The fine did little to damage his reputation, though, and in 2003 he saddled his first Group winner and his first Group 1 winner, courtesy of Milk It Mick in the Somerville Tattersall Stakes and the Darley Dewhurst Stakes at Newmarket within the space of two weeks in October.
Osborne, 50, now runs two yards, one at either end of Upper Lambourn, and has capacity for 80 horses. In January, 2018, he admitted to “living the dream” when he saddled Toast Of New York in the Pegasus World Cup – the most valuable race in the world, with a first prize of $7 million – at Gulfstream Park, Florida.
Prior to winning a small conditions stakes race at Lingfield the previous December, Toast Of New York had been off the course for 1130 days since just missing out in the Breeders’ Cup Classic at Santa Anita Park, California in November, 2014. Toast Of New York was soon struggling and eventually finish last of the twelve runners, beaten 50 lengths, behind the hot favourite Gun Runner. Nevertheless, a defiant Osborne said afterwards, “I know I look slightly silly bringing him here now, but I still believe wholeheartedly that he is capable of competing at this level.