History at Doncaster — but Saffie Osborne’s St Leger triumph was about more than being first
For all the anticipation surrounding the 250th running of the St Leger, Doncaster could hardly have scripted what eventually happened. The oldest Classic in the world had spent much of the week looking backwards at its history, only for Saffie Osborne and Highwayman to provide it with an entirely new chapter.
Osborne became the first woman to ride the winner of a British Classic, an achievement that will inevitably follow her throughout the rest of her career, but there was something about the manner of Saturday’s victory that made it particularly satisfying. This was not a jockey clinging on aboard an overwhelming favourite, nor was it a race decided by circumstance. Highwayman was an 11-1 chance who needed to improve again, and Osborne rode him with the confidence of somebody who realised during the race that she had rather more horse underneath her than perhaps even she had expected.
By the time they reached the business end of the St Leger, the historical significance had become almost secondary to what was happening on the track.
Highwayman travelled beautifully, Osborne allowed him to move into the race and, although she found herself in front earlier than Joseph O’Brien had originally intended, there was little point fighting a horse who was going that well. When stablemate Enceladus attempted to close, Highwayman found again and eventually put two and a half lengths between himself and the runner-up, with Amelia Earhart another four and a quarter lengths behind in third.
It was an emphatic way to make history.
The Highwayman story deserves equal billing
There is an understandable temptation to make everything about Osborne, but Highwayman’s transformation is one of the most remarkable elements of the result.
He was beaten by a considerable number of horses during the first part of his career and initially showed little to suggest that a British Classic lay in his immediate future. Joseph O’Brien himself has admitted that he thought the handicapper had been rather harsh when allocating the colt a mark of 76 after his fourth start.
Then came the distance.
Once asked to race over a mile and a half at Killarney, Highwayman suddenly looked like a different horse, winning his maiden by nine lengths before progressing again over the St Leger trip at Leopardstown. Doncaster demanded another substantial step forward, but instead of exposing him it revealed that the improvement had not finished.
That is one of racing’s enduring fascinations. Ratings, sectional times and increasingly sophisticated data can tell us an enormous amount about what a horse has already done, but they cannot always tell us what a horse is about to become.
Highwayman has travelled an extraordinary distance in a remarkably short period, and it would be dangerous to assume that Doncaster necessarily represents his ceiling.
Joseph O’Brien now has the pleasant problem of deciding what to do with him. Melbourne has been mentioned and so has the Irish Cesarewitch, although neither decision needs to be made in the immediate aftermath of what was comfortably the biggest performance of the horse’s career.
For once, racing might allow the winner to enjoy being a St Leger winner before deciding where he needs to go next.
A landmark that felt completely natural
There have been many important moments for female jockeys in British and Irish racing over the past few decades, and each has made the next one slightly less surprising.
Hayley Turner helped establish that women could compete successfully at the highest level on the Flat. Hollie Doyle pushed those boundaries considerably further and became the first woman to win a major European Classic aboard Nashwa in the Prix de Diane, while Rachael Blackmore’s achievements over jumps, most famously becoming the first female jockey to win the Grand National, altered perceptions on an altogether different scale.
Osborne’s St Leger now belongs in that company.
Yet perhaps the most significant thing about her victory was that the opportunity itself was so ordinary.
At the beginning of the week Osborne did not have a ride in the St Leger. Joseph O’Brien needed jockeys, her agent Tony Hind had riders available and Highwayman became hers. There was no grand announcement about providing an opportunity to a female jockey and no publicity campaign surrounding the booking.
She was available. She was good enough. She got the ride.
Then she won.
That should matter every bit as much as the record itself because genuine equality in sport is reached not when opportunities are created for symbolic reasons, but when the identity of the person taking them ceases to require an explanation.
Osborne’s reaction afterwards showed what the achievement meant personally. She spoke about the influence of riders such as Turner and Doyle and admitted the occasion had overwhelmed her emotionally, describing it as something nobody could ever take away.
At 24, she is entitled to believe there are considerably more important afternoons ahead of her.
Joseph O’Brien quietly produced another masterclass
There is another name that should not disappear beneath Saturday’s headline.
Joseph O’Brien trained the first two home.
That is a considerable achievement in any Classic and another reminder of how formidable an operation O’Brien has built since moving into training. Highwayman was not an obvious St Leger horse earlier in the year, yet his trainer found the key to him, moved him through the grades quickly and arrived at Doncaster with a colt still progressing.
Enceladus then followed him home.
O’Brien was not even at Doncaster to enjoy it, watching from Leopardstown instead, but perhaps there was something fitting about that. His influence on the result had largely been exercised long before the horses entered the Town Moor straight.
Good training is often most obvious when very little appears to be happening.
A result that will outlive the anniversary
The 250th St Leger was always going to be remembered. Doncaster had rightly made much of the anniversary and more than 30,000 people were there to see one of British racing’s great old races reach another landmark.
What nobody could guarantee was a race worthy of the occasion.
They got one.
Highwayman produced the performance, Joseph O’Brien produced the first two home and Saffie Osborne supplied the piece of history that will ensure the 2026 St Leger occupies rather more than another line in the record book.
Yesterday we wondered whether she could do it.
Today we know.
The more interesting question now is whether, years from now, we will regard Doncaster as the day Saffie Osborne broke through a barrier or simply as the afternoon one of Britain’s leading jockeys won her first Classic.
Perhaps the latter would be the greater legacy.
John Mills’ View
I’ve watched racing change enormously over the years, and I think we occasionally make the mistake of looking for progress in grand announcements when the real evidence is usually much simpler.
Saffie Osborne getting the ride on Highwayman is a perfect example. She wasn’t booked because somebody wanted to make history; she was booked because Joseph O’Brien needed a jockey and she was one of the best available. Once she got the opportunity, she was good enough to take it.
That is why Saturday matters.
I also wouldn’t allow the historical story to overshadow Highwayman because this is a fascinating horse. We said before the race that rapidly improving horses are dangerous precisely because nobody knows where their ceiling is, and he proved the point rather emphatically. A horse who looked ordinary early in the season is now a Classic winner, and the frightening thing for his future opponents is that I’m still not convinced we’ve seen the finished article.
There will inevitably be talk about Melbourne and plenty of other targets, but that can wait.
For one Sunday morning at least, Highwayman is the St Leger winner and Saffie Osborne is a British Classic-winning jockey.
Nobody can take either of those things away from them.
— John Mills
