
‘Racing's big spender' went from uni dropout on £7.40-an-hour at Toyota to giving tours of his Ferrari collection
The Kentucky-based American has only been in the game for a couple of years but has certainly arrived in style.
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Inspired by Ballydoyle's unique Derby gallop that replicates the contours of Epsom, Stewart is in the process of putting together his very own Ascot at his new 300 acre training centre.
'I don't do anything by halves,' he laughs. You quickly get that impression.
When he's not flying around the world on his private jet or adding to his supercar collection, Stewart, 55, runs Resolute Racing — his burgeoning empire.
This week he will don the top hat and tails and jet into Berkshire with his fiancee Chelsey Stone in search of their first Royal winner.
He owns King Charles III favourite Believing in tandem with powerhouse Coolmore and has snapped up Paddy Twomey's juvenile Rogue Legend to run in his own black and blue silks.
It's a hell of a long way from his roots.
He dropped out of college before becoming a factory worker making cars for Toyota.
Years later he would make his fortune in private equity after a spell working in London.
Racing has always been a passion of his and he is making the most of his moment in the limelight.
Stewart said: 'The purses are crap at Ascot but the trophies are awesome!
'Who doesn't want The King to be handing them a trophy?'
The high-flying owner was one of the stars of Netflix's 'Race For The Crown', a series focused on the Triple Crown in America.
New to the scene, he has certainly ruffled some feathers with his opinions and upset some of the more traditional forces.
Off the track he's not shy of getting out the chequebook and the past weeks have been no different.
His team have been scouring Europe for horses that Stewart can run at Ascot.
So what is it that year after year keeps bringing back the Yanks to Ascot?
Stewart said: 'In Europe there is a lot of tradition, that's what a lot of it rests on.
'Who doesn't want to compete at Royal Ascot? It's one of the biggest events around the world, not just in horse racing.
'This will be my second Ascot, I've got all my kit — the top hat is ready to fly over with me.
'And last year I got really bored of Aidan O'Brien and Ryan Moore winning all the cups. Give me a chance to beat Coolmore and I'm there. I'm friends with those guys and I took them to the Superbowl but I wanna' beat them more than anything.
'It's such a great atmosphere at the place that I just couldn't miss out.
'The homebreds are not quite there yet so I needed to top up my team with some ready made talent.
'Last year was my first Ascot and I really got a taste of what it is. I only had a couple of runners and they weren't really contenders.
'But these horses are hard to come by. People joke that I pay too much, they call it a 'Sheikh-like price' but I don't mind! What choice do I have?'
Plenty of flashy new owners make a splash when they enter the game but few go on to achieve the success they dream of early on.
Stewart says he will buck that trend and his empire is growing at a rate of knots.
He added: 'One of the things I wanted to do is build a mile uphill gallop.
'It will be an exact replica of the contours of the straight mile at Ascot. I want to train my horses on that.
'You can't just bring a horse that runs in America on the turning tracks and turn up at Ascot, it doesn't work.
'The horses hit that hill and think 'what the hell is going on?'
'That's how serious I am. People think I will spend some money but then disappear but it's a long-term thing.
'I've loved it for 30 years and started out as a horseplayer like everyone but now I have the means to compete at a high level and I'm trying to build something that's going to be here a long-time.
'I'm trying to promote the industry with every chance I get too. I'm a fan first and foremost and it's surreal for me what I am now doing.'
Stewart is happy to trash talk before a big race too. He often gets into trouble with those close to him for his posts on X but he's drawing in new fans and is that such a bad thing?
You can even sign up for a tour of Stewart's Kentucky farm complete with a glimpse of his supercar shed full of Lamborghinis, Ferraris and Porsches.
He adds: 'I think it is good for the sport to ruffle some feathers. If you don't like the way things are done but you stay quiet you will get nowhere.
'For the average race fan, owners, jockeys, the horses, the trainers . . . they all seem inaccessible.
'They make out they are a special group and if you're not in my group, 'don't hang around me.'
'We don't exist without the horseplayers. The gamblers are the most important part of the sport.
'I've opened up my farm so that people can come and visit and I give as much access as I can.
'I have five or six times the followers on social media than any other owner in America and the majority of my posts are just positive things about the sport and updates on my horses and fans are embracing that approach.
'I seem more like one of them than the rest of the stuffy owners.
'It's an older generation sport and we need to do something about that.'
Whether it's too soon or not for a Stewart winner at Ascot, you'll certainly hear him coming.
So get ready Ascot — the Stewart show is in town.
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