Simon Sherwood: 'We owned up when we heard Jenny Pitman had called the police'

What was your finest hour as a rider?
It has to be winning the Cheltenham Gold Cup in 1989 on Desert Orchid. I remember I had a plan that went out the window when the conditions became so extreme, but looking back it was probably to our advantage that they did, because it made the race all about the ones who could keep jumping in the ground and the ones who had the most guts. My overriding memory is of jumping the last, putting my head down and saying: "You've got to throw everything at it because you'll never get this chance again."

And as a trainer?
My first three runners at the Cheltenham Festival resulted in two winners [Duke Of Monmouth in the Triumph and Dusty Miller in the County] and a third [Latent Talent in the Kim Muir]. I thought it was so easy! I was at least lucky to join an exclusive club of individuals who have ridden and trained a double at the festival.

The West Awake gets Sherwood off to a flier by winning the Sun Alliance Hurdle at Cheltenham in 1987Credit: Mark Cranham

Were you ever going to be anything other than a jockey?
I went to Cirencester Agricultural College and got two diplomas in agriculture, one being in advanced farm management, and the idea was to ride for two seasons as an amateur and then go home to farm. Then I turned professional and later I sort of fell into training.