How Lester Piggott ended Des O'Connor's dream to ride in the amateurs' Derby

Des O'Connor, the comedian, singer and TV presenter who has died at the age of 88, was a keen racing man who had a long connection with the sport.

The star once had ambitions to compete in the amateur riders' Derby, the Moet & Chandon Silver Magnum at Epsom. He rode out at Newmarket but never rode in a race, taking heed of the one-word piece of advice from Lester Piggott: “Don't.”

The most recent horses to carry his pink silks with black stars were trained by Philip Hobbs but his best winner was Bermondsey, who for a previous owner had been unplaced in the 1966 Derby as a 100-1 maiden.

Newmarket trainer Denis Rayson paid 740gns for Bermondsey on behalf of O'Connor at Ascot sales in January 1969, and the gelding then won nine times over jumps in 18 months. He scored three times over hurdles and six times over fences in low-grade company, and champion jockeys Bob Davies, Stan Mellor, Josh Gifford and Terry Biddlecombe all won on him.

Another of his horses, Four Star, won consecutive novice chases when trained by Steve Nesbitt in Yorkshire in 1976. At the time he was a heavy punter, but he then spent many years out of the sport after getting into trouble over unpaid debts with bookmakers.

On O'Connor 's return in 1993 he owned a juvenile hurdle winner, Bonus Point, trained by Mary Reveley, and then had two good horses with Philip Hobbs – Clifton Beat and Quality, who won four and five races respectively for him.

Clifton Beat gave him his biggest victory when landing the Flavel-Leisure Hurdle at Newbury under Graham McCourt in October 1995, with subsequent Gold Cup runner-up Strong Promise among the also-rans. Earlier that year he had been fifth in the Triumph Hurdle and runner-up in the Anniversary Hurdle at Aintree.