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Home » Air of brilliance! Meet the Cheltenham Festival jockey who’s also a pilot… and takes off in the field at the back of his house
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Air of brilliance! Meet the Cheltenham Festival jockey who’s also a pilot… and takes off in the field at the back of his house

By uk-times.com11 March 2026No Comments5 Mins Read
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Air of brilliance! Meet the Cheltenham Festival jockey who’s also a pilot… and takes off in the field at the back of his house
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It’s Cheltenham week, so you will not be surprised to hear this narrative involves a jockey talking animatedly about a flying machine.

There is, however, a genuine and remarkable difference to the usual tone. Sean Flanagan knows all about top-quality horses that float up the gallops but he also knows what it takes to get airborne: apart from being one of the weighing room’s most respected riders, he is also a qualified pilot.

So here we are, on a rainy day in Thurles, one of Ireland’s provincial racecourses, discussing great adventures and big ideas. The venue for the meeting is heavy with symbolism, which we will discuss further in due course, but before that we can get ready for take-off.

‘I have a two-seater plane and I take off in the field at the back of my house, just outside Kells near Dublin,’ says Flanagan, with a nonchalance that makes it sound like he is jumping on a bicycle. ‘I’ve always thought outside the box and I got a present, way back when I was 16, for a flying lesson.

‘I never got it out of my head. Fast forward a few years and I was ill one evening, up in the middle of the night. I was sitting up on the computer and a flying lesson advertisement popped up. 

‘So I said to myself: “Ah, this will put me in good form!”; one lesson a month became two and away we went!

‘I fly myself around the country to meetings. I could fly 100 hours a year, give or take. It’s just brilliant; I’ve landed in plenty of the racecourses. I’ve done Roscommon, Naas, Cork; Gowran Park, Killarney… we’re getting through a few of them.’

Had he not had so much gear to carry with him this week, Flanagan, a father of three who also owns the jockeys’ valeting business, would have taken his own direct route to Cheltenham and he has even flown a six-seater aircraft to give some of his colleagues lifts in the past.

Sean Flanagan wins the Champion Chase on Marine Nationale at Cheltenham last year

One day in the future, when he hangs up his saddle, he could even graduate to flying passenger planes. There would be more exams to pass but, at 37, he is ready to start his studies — a jockey’s career is finite — and the idea of becoming a captain intrigues him.

‘I flew to Cheltenham two years ago,’ he confirms. ‘I flew to Aintree 12 months ago. That was class. Liverpool is so handy, up and over the water, ride your horse and back home in the evening in an hour. 

‘I rode at Ayr last season and that was just fantastic, flying into there. The scenery was unreal.

‘If I go to Donegal, that’s one of the most scenic landings in the world. You’re just up there, watching the world go by. You can be in a real bad mood, in bad form, but then you are up there and it just calms you down. It’s a privilege, like, a total escape from racing.’

Privilege is a marvellous word and you can see he means it. Flanagan should have been preparing today for his spin on an equine aeroplane but Marine Nationale was ruled of the Queen Mother Champion Chase, the race he won 12 months ago, with a freak injury.

There are still good opportunities for him on the card: Vanillier is quietly fancied to run well in the Cross Country Chase, while Release The Beast is well-tuned up for a good crack at the fiendishly competitive Johnny Henderson Grand Annual Chase.

But jockeys put in those painstaking yards, day after day, to have an association with a horse that can take them to a different realm.

So often you hear about the horses lining up and the excitement they bring that it is almost striking to hear about the ones that are not part of the cast list. ‘I got a phone call at 9am last Tuesday morning from Barry (Connell, Marine Nationale’s trainer) and, jeez, it was hard,’ he says with a grimace.

Flanagan leads the field on Sober Glory in Tuesday's Supreme Novices' Hurdle, eventually won by Old Park Star

Flanagan leads the field on Sober Glory in Tuesday’s Supreme Novices’ Hurdle, eventually won by Old Park Star

‘I was on my way down to Naas to ride a favourite and he was ruled out, too, when I got there. Then I fell off my other ride! Those are the days you remember!

‘All you can do is move on. The injury to Marine is nothing serious and he’ll run at Punchestown. You’ve seen him in the flesh, haven’t you? He’s gorgeous. He’s a champion, every inch of him. He’s a once-in-a-lifetime horse, I’ve spent 20 years looking for one as good as him.

‘My kids are at an age now when they are wondering why I’m away so often but they kind of understand that it’s for a horse like him.

‘It would have been a great race with Majborough but we had last year, didn’t we? I will never forget that day, as it was such a surreal rollercoaster of emotions. You reach the top of the straight and you think: “Wow, I’ve just won the Champion Chase” but then it all hits you…’

What made last year’s Champion Chase so exceptionally poignant was the fact Marine Nationale’s former rider, Michael O’Sullivan, had died a month earlier, following a fall at Thurles. A fine young man, with so much to give, his passing had a profound effect.

‘We are standing 50 yards from where the accident happened,’ Flanagan says quietly. ‘I was one of the four riders who had the prospect of being there with Michael, as I fell alongside him. I was the first one to fall at that fence in the incident in that race.

‘Michael spoke to me a lot after I’d got the job with Barry and I got to know him so well in the build up to that. It was a very tough time. Of course, I’m disappointed not to be riding Marine Nationale but you know what is important in life.’

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