Handsome Sailor (30 April 1983 – 1997) was a British Thoroughbred racehorse and sire. A specialist sprinter, he showed useful, but unremarkable form in his first two seasons, winning three of his nine starts as a juvenile and two from four in an abbreviated three-year-old campaign. He emerged as a top-class performer in 1987, winning the Duke of York Stakes in England and the Prix de Ris-Orangis in France. He was even better as a five-year-old, winning a second Duke of York Stakes and adding victories in the Temple Stakes, William Hill Sprint Championship and Prix de l'Abbaye. His form was less impressive in 1989 but ended his racing career with a victory in the Flying Five. He was not a success as a breeding stallion and died in 1997 at the age of fourteen.
Handsome Sailor began his racing career by finishing unplaced in a five furlong selling race but then made steady improvement throughout the year. After winning a maiden race at Windsor Racecourse on his fourth appearance he began to compete in nurseries (handicap races for two-year-olds). He won at Newcastle Racecourse in August and Haydock Park in October. On his final appearance of the year he was narrowly beaten by the filly Catherine's Well when carrying 130 pounds at Doncaster Racecourse in November. He ended the year with a record of three wins, one second and one third place from nine starts. The independent Timeform organisation gave him a rating of 111, twenty-one pounds behind their top-rated juvenile Huntingdale and described him as a "genuine" colt who was very well suited by soft ground.
At the end of the year the colt was bought privately by Robert Sangster and was sent to Michael W. Dickinson's stable at Manton, Wiltshire. Sangster reportedly intended that Handsome Sailor would act as a lead horse in training gallops for the yard's more highly regarded horses.
At the end of the year Dickinson ceased to train for Sangster, with Barry Hills moving from Lambourn to take over the Manton stable.
At Royal Ascot in June Handsome Sailor contested the Cork and Orrery Stakes and finished third behind Big Shuffle and Ongoing Situation. In July the colt was sent to France Prix de Ris-Orangis over 1200 metres at Évry Racecourse and started second favourite behind the French filly Tenue de Soiree. Ridden by the Australian jockey Ron Quinton, Handsome Sailor lead for most of the way and rallied after being headed in the closing stages to win by three quarters of a length from Tenue de Soiree. He returned to France for the Prix Maurice de Gheest at Deauville Racecourse in August but after leading with 400 metres left to run he finished fourth behind the British-trained filly Interval.
Handsome Sailor ran twice in the autumn and was well-beaten on both occasions. In the Haydock Sprint Cup on 5 September he was ridden by his trainer's son Michael Hills and finished third behind Ajdal and Sharp Romance, with Interval in fifth. On his final appearance of the season he ran disappointingly when unplaced behind Dowsing in the Diadem Stakes. Timeform gave him an end-of-year rating of 117, thirteen pounds behind their top-sprinter Ajdal. In the official International Classification he was rated the second best older sprinter in Europe two pounds behind Hallgate.
For the second year in succession, Handsome Sailor was beaten in the Cork & Orrery Stakes at Ascot in June, finishing sixth behind the three-year-old filly Posada. In the following month he contested the Group One July Cup at Newmarket and finished third behind Soviet Star and Big Shuffle. On 18 August at York Handsome Sailor was one of twelve horses to contest the Group One William Hill Sprint Championship and started the 5/2 favourite ahead of Perion and the three-year-old filly Silver Fling (winner of the King George Stakes). The other runners included Cadeaux Genereux, Gallic League, Colmore Row (Norfolk Stakes) and Rotherfield Greys (Stewards' Cup). Handsome Sailor was amongst the leaders from the start, went to the front a furlong and a half from the finish and stayed on to win by one and a half lengths from Silver Fling with Perion a head away in third.
Handsome Sailor's next race was the Sprint Cup at Haydock Park on 3 September. Racing over six furlongs on heavy ground he led till half way before fading to finish fifth of the ten runners behind Dowsing. For his final European start of the season, the horse was sent to France for the Group One Prix de l'Abbaye over 1000 metres at Longchamp Racecourse on 2 October. His eight opponents included Big Shuffle, Cadeaux Genereux, Silver Fling, Sharp Romance, Caerwent (International Stakes), Bluebook (Prix de Seine-et-Oise) and La Grande Epoque (runner-up in the race in 1987). Handsome Sailor took the lead from the start but was overtaken 200 metres from the finish and beaten into second place by Cadeaux Genereux. The local stewards however, found that the "winner" had caused interference in the early stages: Cadeaux Genereux was disqualified and the race awarded to Handsome Sailor. Three weeks later the horse was sent to the United States for the Laurel Dash over six furlongs at Laurel Park Racecourse but made little impact, finishing fifth behind Steinlen.
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