Dr Devious

In the spring of 1991, the two-year-old Dr Devious won the May Maiden Stakes at Newbury, then in June ran second in the Coventry Stakes at Royal Ascot. Ridden for the remainder of the year by Willie Carson, in July he won the Superlative Stakes at Newmarket and in August the Vintage Stakes at Goodwood Racecourse. The horse had been sold by Robert Sangster to Luciano Gaucci before the Vintage Stakes, but the agreement was that he would be leased back to Sangster for his next two races.[8] Back at Newmarket, on 2 October he finished a head second to Young Senor in a crowded field in the Tiffany Highflyer Stakes then just over two weeks later (wearing the Gaucci colours for the first time) ran in the Group One seven furlong Dewhurst Stakes, Britain's most prestigious race for two-year-olds. He took the lead a furlong from the finish and won by two and a half lengths from Great Palm.[9]

American Jenny Craig purchased Dr Devious for a reported $2.5 million as a gift for her husband Sidney.[10] In April 1992, Dr Devious finished second to Alnasr Alwasheek under the French-based American jockey Cash Asmussen in the Craven Stakes. In May of that year, the colt was shipped to Churchill Downs in Louisville, Kentucky, to compete in America's most prestigious horse race, the Kentucky Derby. Racing on dirt, Dr Devious finished seventh to winner Lil E. Tee. After the race, Sidney Craig asked the advice of his American trainer, Ron McAnally, who advised him that Dr Devious was a turf specialist and that he should send the colt back to England.[11]

Dr Devious returned to England to run in the Epsom Derby on 3 June. Starting the 8/1 second favourite in a field of eighteen, he took the lead a furlong from the finish and held off the challenges of St Jovite and Silver Wisp to win by two lengths.[12]

Three and a half weeks after his Epsom win, Dr Devious met St Jovite again in the Irish Derby at the Curragh. Dr Devious was made odds-on favourite but was never able to make a serious challenge to St Jovite, who won by twelve lengths in record time.[13] Dr Devious finished fourth in the International Stakes at York in August and then ran against St Jovite for a third time in the Irish Champion Stakes over ten furlongs. The two horses raced head-to-head down the straight with Dr Devious moving ahead near the post and winning by a short head.[14]

Dr Devious ran three more times without recovering his best form. He finished sixth in the Prix de l'Arc de Triomphe, fourth in the Breeders' Cup Turf, and unplaced on his final start in the Japan Cup.[15]