How a naive Denis O'Regan was pranked by colleagues - only for his Gold Cup-winning boss to turn the tables

Denis O'Regan has recalled his naivete as a young man starting out in the sport that saw him become easy prey to a wind-up by fellow stable staff at the yard of his first boss Francis Flood.

O'Regan was speaking to the Racing Post for a major interview in Sunday's newspaper in which he discusses his reasons for quitting the saddle after a phenomenal career, the culture shock of moving from Ireland to the north of England that led to some of his toughest times and his early breaks in the sport.

Obsessed with horses from a young age, O'Regan honed his horsemanship on Shetland ponies from the age of five and chuckled as he recalled a somewhat free-range childhood.

“My dad got me a Connemara and I would tack up in the morning and ride four miles over to a friend’s farm where we’d tie up the ponies and play around the farm until ten at night and then ride home again without any lights at all,” he said. “I remember once we were out on our ponies and I went behind one to try to get him to jump a river and he double barrelled [kicked] me. When my father came to collect me, I was laid out on the back of the pony like an old cowboy that was after getting shot. All he says is, ‘Come on, get off him, you’ll be grand.’ That’s the way my father is, very tough, says very little, but what he does say you’d listen to.”

Later, O'Regan landed a summer job with Flood, the 1972 Cheltenham Gold Cup winner based in Wicklow, and was offered a full-time job a year later when he left school, even though he was evidently still running very green - something fellow staff were quick to exploit.

“I was only there a week and I was starving hungry after working three lots,” he explained. “Josh Byrne was an amateur there at the time and I asked him what you did for food around here and he says, ‘You just go up to the boss and ask him to cook you a hot breakfast.’ Then another lad says, ‘Sure, if you’re going up you might as well get me a bacon butty too.’

"So off I go up to the house and knock at the door and Francis comes out and I tell him that Josh sent me up for my breakfast. 'Did he really, now?' he asks and then brings me in, sits me down and makes me a lovely big breakfast with all the trappings. He did it just to annoy the boys.”

Read more from Denis O'Regan in The Big Read, available in Sunday's newspaper or online for Members' Club Ultimate subscribers from 6pm on Saturday. Click here to sign up.

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