Who is the only jockey to have won the Derby and the Kentucky Derby?

The Derby is run over a mile and a half, on turf, at Epsom Downs, Surrey on the first Saturday in June, while the Kentucky Derby is run over a mile and a quarter, on dirt, at Churchill Downs, Kentucky on the first Saturday in May. Both races are open to three-year-old colts and fillies – and geldings, in the case of the ‘Run for the Roses’ – but granted their proximity, the different surfaces involved and the necessity for a transatlantic flight, it should come as no surprise to learn that no horse has ever won both races.

That said, two have tried; in 1986, Bold Arrangement, trained by Clive Brittain, finished second at Churchill Downs and fourteenth at Epsom while, in 1992, Dr. Devious, trained by Peter Chapple-Hyam, finished seventh at Churchill Downs, but recovered sufficiently to collect the then-£355,000 first prize money at Epsom a month later. According to Chapple-Hyam, “He [Dr. Devious] wasn’t going to run in the Derby after that, but he was so well when he got home [from Kentucky] that he got loose a couple of days later. “

Likewise, several jockeys have attempted to complete the Kentucky Derby – Derby double, but so far just one has succeeded. Steve Cauthen, nicknamed the ‘Kentucky Kid’ as a teenager, rode Affirmed, trained by Lazaro ‘Laz’ Barrera, to victory in the Kentucky Derby, Preakness Stakes and Belmont Stakes in 1978, thereby becoming the youngest-ever jockey to win the American Triple Crown.

Cauthen was still only 19 when he moved to Britain and, having subsequently succeeded Lester Piggott as stable jockey to Henry (later Sir Henry) Cecil, went on to win 10 British Classics. He won the Derby twice, on Slip Anchor, owned by Lord Howard de Walden, in 1985 and Reference Point, owned by Louis Freedman, in 1987.