At the 250th running of the St Leger Stakes at Doncaster Racecourse, history was made as jockey Saffie Osborne guided the three-year-old colt Highwayman to victory, marking the first time a female jockey has won one of British flat racing’s five Classic races.

Highwayman, bred in Normandy and trained by Joseph O’Brien in County Kilkenny, Ireland, had a modest beginning. Initially offered for sale at the Deauville sales two years ago with a reserve price of €19,000, the young colt failed to attract a buyer at the auction and was retained by his breeder, Thierry de la Heronniere, before being sold privately. Following his arrival at O’Brien’s yard in February, Highwayman had a slow start to his racing career, running unplaced in his first three attempts over the summer of his two-year-old season. He was not immediately assigned an official handicap rating due to his lackluster performances.

The turning point came during a race at Naas in August, where, despite starting at odds of 250-1, Highwayman demonstrated a remarkable burst of acceleration in the final stages, catching the attention of his connections. Shortly thereafter, he secured a commanding nine-length victory at Killarney, signaling his rapid improvement. Building on this performance, Highwayman then won the Vinnie Roe Stakes at Leopardstown at odds of 22-1, solidifying his status as a serious contender.

Joseph O’Brien, reflecting on the colt’s development, acknowledged that Highwayman was ready for a greater challenge, setting sights on the St Leger as the ultimate prize. Saffie Osborne, 24, whose family background includes a jump jockey father and an equine artist mother, had never before ridden Highwayman prior to their historic success at Doncaster three weeks ago. Their partnership culminated in breaking new ground for female riders in flat racing’s most prestigious events.

Osborne, who had first encountered O’Brien 14 years earlier at the Derby, expressed the significance of the victory, noting that achieving a Classic win tempered previous fears about her career aspirations. The win at Doncaster not only cemented her place in racing history but also underscored the evolving landscape of British flat racing, where barriers continue to be challenged and milestones reached.