Record-breaking jockey Saffie Osborne relives the ‘shock’ win that’s ‘changed her life’

This won’t change Joseph’s life, but it’s changed mine,” said Saffie Osborne, moments after her record-breaking St Leger win.

Saffie didn’t even have a ride in the St Leger on the Monday before the race. Less than a week later, she piloted the Joseph O’Brien-trained Highwayman into the history books at Doncaster, becoming the first woman to win a British Classic.

Outwardly her life is the same, albeit much busier than she has ever been with media commitments, trying to say “yes” to as many as she feasibly can. The racing wheel keeps on turning and Saffie goes to work – Sandown, Ayr, Ffos Las, Goodwood, Newmarket, back to Wales – riding five to eight horses a day. Even on her one day off, Saffie was on a horse, showjumping at the Newmarket open day.

“I think maybe people took what I said and thought that I meant from an outer perspective,” she says. “For me it changed my life because I grew up as a very competitive person, and I think that fear of failure always drove me.

“After the win, it was the first time that I’ve been able to sit back and relax because I was always terrified of my career finishing and feeling like I failed and I didn’t achieve what I wanted to.

“I feel now like this weight has been lifted off my shoulders and I can actually enjoy it. I’ve achieved one of the biggest things I’ve always wanted to, and hopefully I’ll achieve so much more. But this is one thing that I can always look back on in my career and think, ‘I did that.’

“So rather than what it’s done for my life from an outside perspective, it’s more a case of what it’s done for me.

“I’m competing against some of the best jockeys in the world, and you’re constantly trying not to compare yourself. To have such a big one ticked off, to have won a British Classic, which we all know how hard they are to win, has changed my mindset.”

“Like I’d been chucked in a tornado and spat out”

In the hectic days that followed, there were few chances to stop and let it sink in. Saffie emphasises how kind it is of all those who messaged her, and making sure she gets back to everyone is on her mind. Among them was a phone call from Sir Michael Stoute, for whom Saffie rode during his last couple of years training.

“That was really special,” she says. “It kind of felt like I’d been sort of chucked into a tornado and spat out. It was funny, I woke up the next day and I think I’d had such an adrenaline high that I had the worst headache on Sunday morning. I hadn’t even had a drink and felt hungover from the whole rush.”

Saffie’s mother, equine artist Katie O’Sullivan, was at Cornbury Horse Trials with Saffie’s aunt and Jayne McGivern, while her father, trainer Jamie Osborne, was at Bath racecourse. Saffie laughs as she pictures how they described their reactions, screaming in excitement against the genteel backdrops of eventing showjumping and a pleasant family raceday.

“I remember walking into the parade ring for the next race and I felt like I’d just done a 24-hour gym session, my whole body was shaking,” she says.

“When Dad rang me, he just said: ‘This is my proudest day on earth,’ and that really got to me.

“I’ve had little moments where it’s really sunk in, and you’re like, ‘Oh my God, that did actually happen?’ I did that. I wasn’t dreaming – because I do have dreams about things like that, then wake up and think, ‘Damn it!’

“I think I was too overwhelmed the day after to take it all in. I remember when Rachael Blackmore won the Grand National and said, ‘I can’t believe I’m Rachael Blackmore.’ There was always going to be a woman who would win a first Classic. It was always going to happen at some point, I can’t believe that was me.”

To win a British Classic is an achievement that most jockeys will never reach in their careers. It’s a milestone moment for women in sport too.

“The reality is, if you’re good enough, you’ll get opportunities. Enough people have proved that at this point,” says Saffie, adding that the likes of famous female jockeys Hayley Turner and Hollie Doyle have paved the way to a point where she is not viewed differently in terms of ability by being a woman.

“Yes, hopefully it might encourage more women to get into racing or little girls to want to be jockeys. But I don’t think it changes the opportunities you get, you get those off merit.”

Winning St Leger was “a complete shock”

Highwayman, 3.35pm Doncaster, trainer Joseph O’Brien. The defining moment of Saffie’s career to date appeared unremarkably as a line of text in the booked rides section on her online racing admin account.

“That’s the amazing thing about this game,” she says. “You never know when the next
big opportunity is going to come, so you have to make sure you’re always ready for it.”

Saffie adds that even though she had spent the week dreaming about winning, when
that moment came, she was in “complete shock”.

“When I crossed the line I just couldn’t believe it. In my interview, I said, ‘I’m speechless. I don’t think I’ve ever been speechless in my life’ – and I haven’t! But I also think that because racing is so turbulent, I’ve devised this way of staying in the middle,” she says.

“I suppose when I was eventing and it was weekend to weekend, your good result lasted longer. Whereas it changes so quickly in racing. I think the St Leger was like the first time that I’ve let myself feel everything.”

To look at Saffie’s career in cold hard numbers, it’s a constant upward trajectory. Riding out her claim, tick, first Group and domestic Group winners, tick, tick, and now a British Classic victory.

Damned statistics never tell the full truth.

At Royal Ascot this year, Saffie came home with a handful of placings. On paper it sounds tidy. For the most part, it was, and for those, Saffie wouldn’t have done anything different: the horses ran well, finishing second is part of sport.

But context is everything when defining whether second is a celebration or a sting, and Touleen’s bridesmaid position in the Group One Coronation Stakes after being boxed in, a hard luck story of the royal meeting, was “painful” to swallow.

“Touleen really hurt, as it felt like there were a lot of eyes on her,” says Saffie. “She’d been a very good two-year-old and it was one of those moments where you just want to curl up into a ball and not come out.

“We’re employed to do a job, if you mess that job up, you know they’re probably going to get someone else. I don’t have a big job, so when you get those opportunities and something doesn’t go to plan, you don’t know when that next big opportunity is going to come along.”

She adds: “After Touleen got beat, Dad and I had a few conversations. I got into a rut, and even though I was riding lots of winners after Ascot, it was that one thing that just sticks with you. You have that doubt in your mind, that moment of feeling, am I good enough? Is everyone looking at me thinking she’s not able to produce at the top level?

“It does eventually get to you when you convince yourself people are thinking that.

“I went into Dad’s office on the morning of King George Day and told him I was struggling mentally, that I’d not enjoyed the last month since Ascot, and it was just getting me down, probably feeling a bit sorry for myself.

“He said, ‘Well, if it’s not making you happy, go and do something else.’ That
was that.

Then he sent me a very long message, basically saying, ‘Just remember, you can do whatever makes you happy for the rest of your life, but now is the only time you can do this. You need to enjoy it now because you don’t want to look back in 10 years and feel like you didn’t enjoy it.

“‘Concentrate on yourself, don’t worry about others, and just remember, you’ll always be happy if you can look back on it and know you enjoyed it.’

“That changed my mindset. I thought, ‘Why am I so worried about all the outside noise and constantly putting this pressure on myself that I’m not achieving what I felt like I should be?’ He then followed up after I rode the treble that day and said, ‘You’re an idiot,’ in typical Dad fashion!”

She smiles, reflecting on that memory.

“He’s a deep thinker, but he’s very funny as well,” she says.

“I’ve had lots of interviews where people ask what I would like to win. And the first thing I’ve always said is that I want to be able to look back and know that I enjoyed every second of it. So that’s first and foremost, but there’s obviously a whole list of races everyone wants to win.”

A British Classic was high up on that list, which also includes as many Group Ones as possible as well as the champion jockey title.

“I always knew I liked winning. I’ve got three older brothers, I didn’t get to win much as a child,” she says.

Looking back... and forward

Saffie was the only one of her siblings to go down the equestrian route, and her desire to learn to ride was self-driven. She loves winning, yes, but her love of horses is her why.

“Everyone at Dad’s yard jokes that I’m the chief pony patter. I love being around them; they’re incredible animals. The life that they’ve given not only me, but my family too…,” she says.

“I think children having ponies and horses is amazing; it teaches them how to care for something that’s not just themselves.

“And even if I was never going to be a jockey or an event rider, competing teaches this amazing mental strength.”

She recalls competing in working hunter qualifiers for major shows and jumping last for team and individual gold at the pony eventing Europeans, reflecting on how she learnt to feel pressure and understand her own response to it.

“I now know that doing my job, where I’m being employed to ride unbelievably expensive horses by trainers and owners and there’s so much resting on every result, that there’s no doubt in my mind that I can deal with it all,” she says. “I embrace pressure; I feel it, but it makes me better.”

In the immediate future, horses will take Saffie to Hong Kong, one of only four European jockeys to be granted a licence there this winter. Australia and the US are on the table, and stints in Dubai next year.

“I feel so lucky. I’m 24 and I’ve been able to travel the world riding horses. If you’d told me that as a kid, I’d have said that’s the dream life,” she says. “This is all I’ve ever dreamed of, and I get to live it.”

• For more exclusive insights into top riders and their horses, subscribe to the Horse & Hound website