Saffie Osborne is still coming to terms with the fact she is a Classic-winning jockey five days on from “achieving a childhood dream” in becoming the first female to ride a winner of one of the five most prestigious events in British Flat racing.
Osborne, daughter of former jumps jockey and Lambourn-based trainer, Jamie, was booked by Joseph O’Brien for the spare ride aboard progressive colt Highwayman in the 250th edition of the Betfred St Leger, with the County Kilkenny trainer’s number one jockey Dylan Browne McMonagle sidelined through injury following a fall at Bellewstown on August 25.
Osborne couldn’t hold back the tears at Doncaster last Saturday after steering 11/1 shot Highwayman to a two and a half-length victory over stablemate Enceladus and admits some of the wider coverage of her success has felt “surreal”.
"It’s amazing how a few minutes can completely change your life,” she said on a Thursday press conference call organised by Great British Racing.
"I remember the moments after the race, I really wanted to soak it all in. Because it’s a feeling I never experienced before and you devise this way of staying very in the middle of everything, not getting too high or too low, and it was the first time I really let myself feel the emotion.
“Afterwards, in a way it feels like this whole season has been building up to a moment like that. I know I’ve worked extremely hard to put myself in the position to get a ride like I did on Saturday, but a lot of things have to happen for me to end up on that horse; the Irish Champions Festival being on, Dylan Browne McMonagle being injured, a lot of the English jockeys being in Ireland or elsewhere…
“However hard you work, you do require a little bit luck.
“It’s been pretty hectic, I’ve been doing my actual job everyday and then trying to fit in as much (media) as possible but I’m very grateful. I know how quickly your fortunes can change in this sport so when everyone wants to speak to you, you've got to make the most of it.
"People say all kinds of stuff but I was no different a rider on Friday as I was on Sunday, so I suppose I’ve just gone about my job doing my best on every horse, but I was doing BBC Breakfast yesterday morning and stuff like that which is slightly surreal, and probably a position I never thought I’d be in, but I’ve had so many people say nice things, coming up at the races and stuff like that so it’s been pretty hectic but special at the same time."
WATCH: Highwayman gallops into history books at Doncaster
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Hollie Doyle, who was the first female jockey to be placed in a British Classic when riding Nashwa to finish third in the 2022 Oaks at Epsom, was among her many well-wishers and countless messages, while another succinct note stood out for the 24-year-old Osborne, who previously won medals at pony, junior and European level as a three-day eventer prior to her switch to horse racing.
"Hollie sent me a message to say well done and make sure you enjoy it all. One of my favourite ones was from (Cheltenham Festival-winning trainer) Richard Phillips, who a while ago – I think it was in 2021 – had said to me that Hollie Doyle might end up being the first female to be champion jockey but you’ll be the first to win a British Classic. And he sent a message on Saturday just saying ‘I told you’. So I enjoyed that one.
"But I’ve been getting messages off people I haven’t heard from in years which has been nice. On the day I made sure I spoke to all the people I was closest with and all the people that had helped me because they know how hard it is, how much you go through, the trials and tribulations of it all, so it was really nice to speak to them on the day and tell them how grateful I was.
“It has been hectic, but it attracts a broader audience to racing and if I can help that happen in any way then that’s a real honour, because it’s an amazing sport with amazing stories to tell.
“I never set out to be an inspiration to anyone, I ride horses and I do my job and I love it, but if what happened on Saturday has done anything, maybe it might encourage more girls to be jockeys, but the reality of it is that this is a multi-million pound industry. People aren’t going to be putting jockeys on their horses that they don’t think are capable.
“I don’t think there is a lack of opportunity for female riders, I haven’t been viewed any differently. I was like any other apprentice just starting that wasn’t Billy Loughnane, it takes a while for you to really get the hang of it and get good.
“I’ve been riding six years now and this year and last year are really the times I’ve got these big opportunities and I think that’s right. I wasn’t ready four years ago, to have opportunities like this.
"There are plenty of days sat in that weighing room and I’m the only girl there and that’s a lot of the time now with Hollie being injured, but I think the girls that have done well have proven that if you’re good enough, you’ll do well.
“The person it was hardest for was Hayley Turner (rode 1000 winners in Britain including two Group 1s) who completely proved that if you’re good enough, you’ll get opportunities, and Hollie took it to another level.
“But it’s been really cool, it was Family Funday at Doncaster on Sunday and some little girls came up to me to ask for a photo and things, I think that was a real full-circle moment for me as I remember being one of those little girls. I’ve still got a photo of me and Hayley when I was around 10, so that was special.”
The 2026 campaign hasn’t been all plain-sailing for Osborne, who admits to hitting a particularly low point following a disappointing five days at Royal Ascot.
Her father first hit the headlines as a 24-year-old at the Cheltenham Festival, winning five races during the meeting in 1992, so was in a very good position to offer some sound advice when required.
"I suppose people think that having a father as a trainer and used to be a jockey that he’d be handing out advice left, right and centre, but he really doesn’t. He’s spent the whole of my career just letting me get on with it, and if I needed some advice then he gave it to me.
“But the lack of advice he’s given me means the stuff that he does say really sticks with me and I remember him saying to me midway through the season, and I was at a bit of a low point after Royal Ascot, it was tough and I was struggling to get past it all mentally.
"He just said 'this isn’t going to be forever, you need to enjoy every single moment of it, remember how lucky you are to do this every day', because I do love doing it every day. And he said 'you’re not going to get to do this forever and one day you’ll want to look back on it and say you enjoyed every minute of it'.
“After Royal Ascot it was tough, there were a few weeks where it felt really hard. Touleen (second in the Coronation Stakes) was one of those moments where I just sat there and felt ‘when it this going to go right for me?’ and you kind of have that seed of doubt in the back of your mind of ‘am I good enough?’ or are people looking at me and thinking 'she can't produce at the top level', stuff like that.
“But I think fear of failure has always driven me. I’ve always wanted to, whatever I was doing, try and be the best at it and I think ever since starting racing, back to what Dad said about this isn’t going to be forever, I was always terrified of retiring one day and feeling like I didn’t achieve what I wanted to.
“Trust me, a British Classic was very high up on that list!
"So I feel almost a sense of relief, firstly that I can’t believe that it's happened, but secondly, this sense of relief that whatever happens for the rest of my career, I can always look back on that day and feel like I achieved a childhood dream."
That dream began at a tender age for Osborne, who as well as spending a lot of time learning from her father, went on to gain work experience with the likes of Aidan O’Brien at his legendary Ballydoyle base, plus Ciaron Maher and Gai Waterhouse in Australia.
“I was riding out for Dad from the ages of about 12 or 13,” she said. "I was riding out four lots for Dad every morning and then going and riding all the eventers as well.
“I think as soon as I started riding out, I thought this is what I want to do. I kind of owed it to myself and owned it to Lord and Lady Blyth, who owned the horses that I rode when eventing, to continue to do it for a while and I also loved it, I got great satisfaction and joy out of producing and riding these horses to a top level. So I don’t think there was a lightbulb moment because it was always what I was going to do from when I started riding out.
“I went to Ballydoyle and spent a season there which was incredible, I learnt so much and rode some amazing horses. It was like a kid walking into a candy-shop. I went from riding out for Dad and then walking in and every horse having their name on their saddle cloths and you’re looking at the likes of Kew Gardens and Japan and all these incredible horses that you’re in total awe of.
“That was amazing and I spent the winter in Australia with Ciaron Maher who told me I’d had too much fun so he sent me to Gai Waterhouse for a month! Which was amazing.
“That’s the one benefit, when people say your Dad’s a trainer, I’ve grown up in racing and really understand the full picture. I’ve grown up being obsessed with it and going to Aidan’s and then Australia stood me in good stead, I got a really good overview of the industry.”
Osborne was injured in the run-up to the Ayr Gold Cup Festival 12 months ago but, after booting home a Thursday double on Wild Thoughts and Ice Cube, looks to keep the ball rolling and continue her strong association with the Richard Spencer stable in Saturday’s feature handicap north of the border.
She’s declared to ride the in-form seven-year-old Twilight Calls for owner Phil Cunningham and hopes are high the veteran sprinter can produce another bold show after his narrow second at Doncaster last weekend.
“I was quite frustrated after the Portland, I was probably drawn on the wrong side but he’s not a horse who does a huge amount when he hits the front and I didn’t really have a horse to take me into the race and had to progress through the race when I did. He probably got a little bit lonely and could have done with something to follow," said Osborne.
"The benefit of that is that he goes into Ayr without a penalty, he sneaks in at the bottom of the weights, and he’s just thrived. He hasn’t been out of the first two all year. He’s a great horse to ride, he’s like a motorbike when you’re trying to pick your way through the whole pack and he really suits these big (field) races.
"He was a very good horse in his day and he still retains a huge amount of that ability, he just needs everything to go right for him."
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