WE meet three days before the seismic event. Perched on a sofa in the café at The National Stud in Newmarket. Saffie Osborne tells me that when her agent, Tony Hind, let on that he was trying to get her a mount in the 250th St Leger, her retort was a caustic ‘good luck with that one, mate.’

“He didn’t even let me know when the ride on Highwayman was confirmed,” Osborne reveals. “I just spotted it come up in my list of booked rides. I’d presumed, if I was getting on anything, I was going to be on a 100/1 shot, so I thought, ‘wait a minute, that’s actually got a chance’.”

The rest, as they say, is history. Little more than 72 hours on and Osborne had become the first female jockey ever to win a British classic. Not that she thinks of herself as a female jockey. She’s just a jockey, pure and simple.

“The way we grew up, I had three older brothers, and I wasn’t treated any differently because I was the youngest or the only girl,” she explains. “So I was a bit of a tomboy. I never remember watching racing and thinking, ‘why are there no girls there?’ I was just thinking: ‘that’s what I want to do’.

“I didn’t have female role models, I just had role models. It never seemed to register in my head that me being a girl would change anything for me wanting to do this. I always thought, ‘if you’re good enough, then you’ll get opportunities’. So I’ve just got to make sure that I’m good enough.”

Five days after we first meet, she very kindly returns my call and I grab a brief reaction to how the Leger triumph has changed her life. “The last couple of days have been a bit surreal,” she acknowledges. “I have been slightly embarrassed at the amount of emotion that came out of me as we pulled up after the race.

“It was an incredible feeling, one that I had never felt before, and since then it’s been a matter of trying to get back to as many people as possible who have sent me some really sweet messages. It was straight back to business, riding at Doncaster the next day, and I am still looking forward to getting the chance to soak it all in.”

Asked what the victory might mean to her career, she replies: “Saturday won’t have changed me as a rider, I’m no better or worse speaking to you now than I was on Saturday morning. But other people’s perceptions of me might have changed and that’s why I am so grateful to Joseph O’Brien and Kevin Blake for giving me the chance to show what I am capable of.

“I’ve always had this fear that I wouldn’t be able to achieve what I wanted during my career, but this is a massive moment that I can always look back on with pride. Becoming a classic-winning jockey was way up at the top of my list of ambitions. It means so much.”

Great expectations

Back to our original rendezvous, she is an engaging interviewee, not afraid to voice some forthright views. Intelligent, analytical, having extremely high expectations of herself in a way that top sportspeople need to, yet at the same time trying to temper her own impatience in getting to the top by realising how hard it will be to reach the summit.

One ingredient of our meeting – her food order - does, however, highlight a huge advantage that she holds over the bulk of her weighing room colleagues. She plumps for a sausage bap with ketchup. Between mouthfuls, she rather sheepishly admits that she has been created at the perfect weight for a jockey, something which will surely aid the longevity of her time in the saddle.

“I’m naturally 8st 2lb, which is our bottom weight, and I find that extremely easy to maintain,” she says. “I haven’t had to sweat once this year and I can’t remember the last time I woke and had to get on a set of scales because I was worried about the weight I was going be.

“I think that Hollie [Doyle] would probably be the only other jockey I know that doesn’t really have to worry about it. I take my hat off to the lads that have to do it every day because it’s tortuous. And, especially with them having taken away the saunas, they’re having to do it some mornings before they go and ride out at 6 o’clock in the morning then drive four hours, dehydrated.

“All of my brothers are six foot plus tall but I’m only five foot five so I won the genetic lottery,” she brags, adopting a very different attitude to your ordinary youngest child, worried about being bullied by their elder siblings.

One other advantage she holds is that she is the daughter of the former top class National Hunt jockey, Jamie Osborne, who, during the past quarter-century, has trained almost 1,000 winners from a yard in Lambourn. Successful in the Dewhurst Stakes way back in 2003, his best horse has been the UAE Derby hero and Breeders’ Cup Classic runner-up, Toast Of New York.

So she has been dealt a pretty powerful hand. Yet hers is not merely a story of hanging on to her father’s coattails, far from it.

With her it is more about talent and her inner drive from a frighteningly young age rather than pushy parents. And my suggestion that she might at some point take over the training licence from her father is met with a firm denial, she wants to plough her own furrow.

“I’m not working as hard as I am now and luckily earning plenty of money to then go and put it into a training business and lose it within six weeks,” she scoffs. “Watching the stress that it puts Dad under a lot of the time, dealing with the staff and the owners, and this horse has gone wrong and that horse has gone wrong and having 25 yearlings to sell.

“I think that Dad would say that I’m not diplomatic enough to train. I know how hard it is. I’ve seen the struggles. When you have a horse like Toast Of New York it’s the best thing ever and the fun me and Dad have now doing it together is amazing. We would not have the same amount of fun if we were both on the training licence together, I can assure you that.

“I’m extremely focussed on what I’m doing now, and don’t think too much about what I’m going to do afterwards.” My guess is that she might become the next Francesca Cumani and she does nothing to dispel that notion, saying: “I’ve done (ITV Racing’s) Opening Show a couple of times this year and really enjoyed it. It’s kind of sad, I’m weirdly obsessed and know all the form lines. I’m not riding today but I’ll still probably watch every race that is run.”

Second career

In fact, at the age of 24, racing is Osborne’s second sporting career, after eventing. At one point, it looked more likely that she would spend her working life competing against Oliver Townend and Ros Canter rather than Ryan Moore and Hollie Doyle. At junior level, she enjoyed almost unadulterated success, winning three silver medals, an individual gold, and a team gold at the Youth European Championships.

So why the switch? Her reply again reveals an astute financial brain, particularly for one so young. “I started riding out when I was 12 or 13 but only really got the racing bug three or four years later,” she says. “I was very lucky with eventing, I was trained quite a lot by [dual Olympic gold medallist] Laura Collett, and that taught me how hard it is.

“Eventers are trying to run a business but not really making any money. There’s no prize money. It’s an amazing sport, but it’s very hard to make any money. I knew that I was never going to be the best at it because I was never going to be able to afford a horse to beat the best.”

International junior eventing competitions gave her a great grounding, in particular at how to cope with highly stressful situations. As she explains: “Eventing didn’t teach me how to ride racehorses but it taught me a huge amount mentally. From a really young age, you’re put under a huge amount of pressure and you either learn how to cope with it or you crumble.

“Going into the showjumping ring, you’re the last one in and you’ve watched another 50 people go before you and you’re thinking to yourself ‘if I have a fence down, I’ll lose a gold medal for myself and I’ll lose a gold medal for the team’.”

Personal best

Even before her historic Leger victory, 2026 was turning into an excellent year for Osborne, with lots of high-profile victories, winners galore placing her firmly within the top 10 of the British Jockeys Championship and the likelihood that she will overhaul her personal best total of 87, set in 2024.

Yet, when I ask how her season is going, her response of ‘better than I thought it would’ is surprisingly downbeat.

“I got injured at the back end of last year and I’d had a really tricky season,” she says.

“Nothing felt like it was falling right, it wasn’t going the way I wanted it to and I didn’t think I was riding very well. Then, in August and September, it was going brilliantly and I got injured and that put a stop to it.

“So, I tried to keep my expectations for this season fairly low because I didn’t want to feel disappointed.

“I knew it was going to take a lot of hard work and I felt like this year was my year to prove that my career hadn’t plateaued. It would be nice to ride 100 winners. But I’m very rarely here for the full year.”

Her new association with trainer Richard Spencer and his backer, the owner-breeder Phil Cunningham, has been a big bright spot. She has ridden for well over 100 different trainers this year but Spencer has provided her with more winners than anyone else, topped by their Weatherbys Super Sprint triumph with Zigazig Ah.

Another bright spot has been the Shergar Cup, the decision to appoint her as captain of the victorious Great Britain and Ireland team, which was completed by Ryan Moore and Dylan Browne McMonagle, no doubt prompted by her bubbly personality and engaging way of dealing with the media.

“I’ve now done the Shergar Cup twice and won it twice,” she enthuses. “I enjoy doing all the interviews, I don’t find it difficult because I live and breathe racing. I do also try to keep myself as well versed in the happenings of the wider world. Racing is unique in that you’re coming across people from every different walk of life and I think being able to hold conversations with them outside of racing is very important.

“The Shergar Cup experience is so fun. The first year I did it, it was amazing to do it with Hollie and Hayley [Turner]. We had so much fun, the three of us, there’s an amazing photo of me and Hollie with Hayley on our shoulders afterwards, it was probably one of my favourite days.

“And I think the whole concept is important in a similar way to how the TV series Drive To Survive helped broaden the appeal of Formula One. I had no interest in Formula One before watching that because I didn’t know any of the people.

“I think racing is quite similar as it’s hard for people to relate to a horse. We get these amazing horses like Frankel and Enable that people become really attached to, but in recent years we maybe haven’t had one of those that’s stuck around, maybe apart from Kyprios or Stradivarius.

“The Shergar Cup is so important and people that want to knock it need to remember it’s only one day of the year. It allows a different audience to come and watch racing. It’s helpful for children to get involved in racing because they can pick a jockey and follow them for the day and they’re in the same colours. They don’t understand the importance of Godolphin or Coolmore, but they can come and watch Ryan Moore and it’s easier for them to follow.”

International travel

Osborne loves the television shows, the regal setting of Ascot and the international travel that her job has afforded her. “In what other world, apart from professional sport, is a 24-year-old paid to travel around the world, riding horses, doing something that I already love doing,” she gushes. “It’s awesome.”

But, sat in front of me in a pale jumper and the baggiest pair of tracksuit bottoms that I’ve ever seen, she does not shy away from the mundanities of a jockey’s life.

“Nowadays the girls have our own separate changing room and, with Hollie out injured at the moment, the sad thing is that I spend most of my days on my own,” she says. “It’s not like I’m excluded from anything, most of us will sit in the canteen at some point and have a bit of banter, that’s one of the highlights of the day.

“But you have to get used to solitary confinement in this sport because you spend hours on your own in the car. You come home and you’re late and you go to sleep and you get up and you ride out and you just do it all over again.”

Not that she would have it any other way, and her ambition to succeed shines through. “In my head, I don’t want to finish my career and feel like I failed,” she admits. “I think that’s my biggest thing. I want to look back on it and feel, firstly, that I loved it, and secondly, I achieved what I wanted to achieve because otherwise, I think it gets really hard to walk away from it.

“I do sometimes end up feeling a bit sorry for myself, such as when Heart Of Honour got beaten by a nose in the UAE Derby last spring. Even this year there have been points when I have been pretty low. Touleen getting beaten in the Coronation Stakes [after suffering interference] was a hard one to swallow. I was really gutted and then you get a microphone shoved in your face ten seconds afterwards, I wish that hadn’t happened.”

Becoming a role model

Ending back on the subject of role models, I suggest that she is likely to have already become one herself, proving that she can compete on a level footing in what is still a very male-dominated profession.

“I never set out to be anyone’s role model, but, if I am, I feel very privileged,” is her response. “In a different sphere, I went to watch eventing when I was a kid and I still have a whole book of autographs from the likes of Piggy French, Pippa Funnell and Mary King [gold medal-winning British three-day event riders]. I actually found the book not that long ago.

“At the time, that was so special to me. If any little girl should view me in the same vein, then I would feel very honoured. I always try to present myself in the best way and make myself as approachable to people as I can, especially children.

“I think it’s quite hard for them to understand exactly what’s going on at a racecourse, so if they meet a jockey, even if they probably don’t know who I am, they might enjoy it more and it’s good for the sport.”

After Highwayman gave her that momentous success at Doncaster last Saturday, Osborne interacted with the media in much the same open, thoughtful and jovial manner that she did during our chat.

Never mind how many more classic winners that she rides, she is set to be a fine ambassador for racing for some time to come.