“I remember handing over a thruppence to a bookie, thinking this is just the best thing you can possibly do!” It’s a crisp autumn afternoon in central London and Chris Giles is reflecting on his racing adventures from the terrace of an exclusive members’ club in the heart of Mayfair.

That early introduction to horses – and betting, more of which later – came at Bogside in Giles’s native Scotland, watching point-to-pointers as a young child with his grandmother at the now defunct racecourse.

Over fifty years later and Giles’s pink and purple silks are among the best known in jump racing, associated with a plethora of top-class horses, from four-time Grade 1 winner Zarkandar and dual King George VI Chase hero Silviniaco Conti through to current stars Greaneteen and Stay Away Fay.

“The racing bug came from my mother’s side of the family, who were Italian immigrants from Tuscany,” he explains. “I’d go to my Gran’s to walk her dog and end up watching the racing on TV.

“When I was older I went to Ayr races. It’s a great racecourse although I’ve had fewer winners there than at a lot of the southern courses. When Rubaud won the Scottish Champion Hurdle in April it was a very proud and happy moment.”

Despite his Scottish roots, Giles was in fact born in Cheltenham, a quirk of fate related to his father’s job with the Road Transport & General Insurance Company. When Giles was two, his family made the move back to Scotland, where dad Michael started Giles Insurance Brokers in 1967.

After boarding school in Edinburgh and having studied English at Oxford University, Giles joined the family business in 1988. With his brother, he led a family buyout in 1995 and turned Giles Insurance Brokers from a partnership into a limited company.

Private equity houses Gresham and then Charterhouse came on board as investors in the noughties and in 2013 the business was sold to American brokerage firm Arthur J Gallagher for £233 million.

Giles explains: “We were a regional company. When I joined in 1988, we had three offices and 20 staff. When it sold to Gallagher, we had had 42 offices and about 2,000 employees.”

Success in the insurance world enabled Giles to indulge his passion for horses, initially north of the border with Lucinda Russell – “I don’t think we had a winner with Lucinda” – before a chance meeting led him to the stable of 14-times champion trainer Paul Nicholls.

‘the good horses find you’

Giles explains: “When I came down south, I met a guy called Mark Tincknell. He was involved in a social housing business called Connaught, which eventually came unstuck. But he was friendly with Paul Nicholls and so we had a few horses together, such as Takeroc and Tchico Polos.”

He continues: “Being in Ditcheat, there is a pecking order, as there is in every yard. A horse called Tricky Trickster came up for sale and I knew he would be expensive, coming from Million In Mind. I bought him – I paid a lot more than I wanted to – but it gave me some status in the yard, and I’ve never really looked back after that.

“Paul has this saying, ‘the good horses find you’. Take Stay Away Fay, for instance. We were all in Harry’s Bar in the west end, celebrating after Greaneteen won the Tingle Creek Chase. We’d had a few drinks when Tom Malone rings, saying ‘I’ve found this horse and you’ve got to buy it’ – it turns into the most expensive evening ever, but that horse found me. I was in the right place at the right time.

“Of course, you can never buy them all because you’d be bankrupt! But I do think that you make your own luck in those situations.”

Stay Away Fay is the latest superstar for Giles, winner of the Grade 1 Albert Bartlett Novices’ Hurdle at the Cheltenham Festival in March, and who made an impressive start to his chasing career when scoring at Exeter last month.

His Festival target this season is the Brown Advisory Novices’ Chase – the six-year-old is unlikely to step out of novice company after his owner was burned in the past from being overly-ambitious with young horses.

Constitution Hill can’t run in them all, can he?

“We made that mistake with Hinterland and Ptit Zig, running against the big boys, and I regretted both,” Giles says. “Hinterland was brought down in the Champion Chase and was never the same horse again, and Ptit Zig fell in the Ascot Chase.

“I leave it to Paul. You’d be a fool to say that Paul and Clifford [Baker] don’t know what they’re doing. We’re also keeping Rubaud over hurdles this year. Constitution Hill can’t run in them all, can he? There’s plenty of good prize-money on offer.”

Despite their abundant talent and promise, Stay Away Fay and Rubaud have some way to go to match the exploits of Silviniaco Conti, winner of two King Georges, two Aintree Bowls, two Betfair Chases and an Ascot Chase during a career that yielded over £1.1 million in prize-money.

Giles owned Silviniaco Conti in partnership with Jared Sullivan. The two later fell out and sold their shared bloodstock interests, which included a Grade 1-winning hurdler stabled with Nicky Henderson, Buveur D’Air. He went on to win a further seven times at the top level, including two Champion Hurdles, in the colours of JP McManus.

Giles says: “Why did we sell Buveur D’Air? Jared ran a very successful recruitment business called Potensis. He had a deal on the table, then Brexit happened – and Brexit was a surprise, of course. That was enough of a change to give the private equity community a fright, so they all downed tools.

“Jared felt he had a lot of bloodstock, so had a dispersal and Buveur D’Air was one of those horses sold, though I bought back Topofthegame.

the one I love the most is Greaneteen

“You want to win the big pots – I think my record now is 22 Grade 1s, including one with Buveur D’Air before we foolishly sold him. JP is a great supporter and I’m delighted the horse did so well for him. But it does hurt a bit when you see a horse you’ve sold win two Champion Hurdles.

“Topofthegame was 100% mine, but I was in the middle of my divorce and the lawyers were telling me not to spend too much money. Paul Barber loved Topofthegame and said to Paul [Nicholls] I’ll give Chris x amount for the horse – that money allowed me to buy Greaneteen. He was the only horse I bought in 2017 because the divorce was pending.

“I loved Conti – he was just a beautiful horse who relished flat tracks – but the one I love the most is Greaneteen, because I always wanted to win the Tingle Creek.

“Sandown was my home course when I lived in Cobham. I used to look at the famous board with the names of the winning horses and owners and say to myself, ‘I have to get on that board’. It’s sentimental; I bought him in the middle of my divorce after Paul Barber’s payment for half of Topofthegame. I have a strange emotional affection for him.”

He continues: “I enjoyed owning with Jared and we had a lot of success together, but it’s inevitable that you have these situations where you don’t agree on everything. Jared is a very forthright guy with strong opinions. Was there a falling out? Yes. We argued about Silviniaco Conti one summer – it was something fairly trivial – but we fell back in again and Crambo is shared.”

Mention of Crambo, trained by Fergal O’Brien, recalls a famous double for his owner at Sandown in March. After the six-year-old had taken the novices’ handicap hurdle, the Nicholls-trained Iceo struck in the next race, the Imperial Cup. Not only did Giles collect a hefty chunk of prize-money, but he had also backed the pair in a double to win a huge sum.

Yet Ladbrokes seemed unimpressed by Giles’s nous in backing his own horses – he’d also had multiple ante-post bets on Stay Away Fay for Cheltenham – and restricted access to his account.

“Ladbrokes did their damnedest to stop me betting,” says Giles. “They wouldn’t let me access the site and kept bouncing me around. I would call it intentional obfuscation.

“I do think that some bookies are using the affordability checks as a battering ram with customers who clearly know what they’re doing.

“I’ve been asked for three years of tax returns and six months of bank statements. People don’t want to provide that – it’s information for your auditor or accountant only. Some bookmakers have been using the guidance to protect themselves.”

He continues: “Betting is a huge part of my interest in racing. I like to bet on my horses, unlike someone like Simon Munir, who told me there’s enough excitement already.

“For me it’s a very important part of the ownership experience and adds to the enjoyment. To a degree we’re back in a nanny state. Smoking’s been banned; I’m not a smoker, but it’s a civil right. This is another example. I’m an entrepreneur, so the less red tape the better.”

Giles is a National Hunt man through and through but has also enjoyed some high-profile successes on the Flat, notably as one of the owners of Tiggy Wiggy, one of the best juveniles of 2014 who captured the Group 1 Cheveley Park Stakes and was later bought by Coolmore for 2.1 million guineas. Yet even that triumph couldn’t entice the owner to invest further.

We went to the winner’s enclosure, but it all felt quite sterile

“I’ve exited the Flat because I found it frustrating,” Giles says. “We have a place in Lisbon where we like to spend the summer, so I’m not in Britain for those months.

“When Tiggy Wiggy won the Cheveley Park, Jared and I were there at Newmarket. We went to the winner’s enclosure, but it all felt quite sterile. There are a lot of people in there but there’s no real warmth, whereas in National Hunt there is. Everyone knows each other, everyone congratulates each other, it’s a nicer community.

“A winner at Cheltenham is just unbelievable. I think the biggest buzz you can get is walking into that winner’s enclosure and seeing those banks of people overlooking the parade ring, cheering, shouting. It’s hairs on the back of your neck stuff.

“I’ve had three winners at the Festival – Zarkandar, Topofthegame and of course Stay Away Fay. I have a small shrine at home with the trophies. Each one was amazing.”

The breeding game has yet to excite Giles although he does have one broodmare, albeit not by design.

“Paul [Nicholls] persuaded me to buy a horse called Jenny Wyse, who hacked up in her point-to-point,” Giles explains. “I told Paul he hadn’t won any Grade 1s with mares, which made him a bit grumpy.

“Anyway, she got a leg, so she’s in foal to Walk In The Park. The idea is to sell if it’s a filly and keep if it’s a colt before gelding and taking the store horse route.

“Jenny Wyse wasn’t cheap – she cost €360,000 – and I wasn’t best pleased [when she got injured] but disappointment is part of the game.”

There have been other disappointments along the way; duo Skatman and Huflower cost £370,000 between them but didn’t work out. He had planned to give them a second lease of life with his son-in-law Tom’s Ronnie Racing syndicate but both pickied up injuries before being retired and rehomed

Among his current 17-horse strong, Giles has high hopes for Jetronic, a £200,000 buy from France through Anthony Bromley, but the four-year-old Reliable Man gelding has not set the world alight in his two runs so far this campaign.

In an industry built on behind-the-scenes trading and private purchases, Giles is refreshingly open about what he pays for bloodstock – “people will find out eventually” – as he looks to find the next runner capable of taking him to the top level.

Giles says he did “very well” when the broker PIB, which he founded in 2014, sold from The Carlyle Group to Apax in 2021. “That’s really what’s fuelled a lot of my recent horse purchases and now I feel I have a pretty decent string.”

The insurance entrepreneur, 59, is still an investor in PIB and works with private equity, but he doesn’t take a salary for these roles, “which means prize-money from horseracing is my only regular income – last season I made about £400,0000, and you don’t get taxed on it”.

Having not worked a 9-5 day for a decade, he has more time to watch horses like Iceo make their chasing debut at Newton Abbot, although with two small children aged five and two – he has three children in their twenties from his first marriage – duties at his Kensington home with Brazilian wife Debora are also important.

The Rangers and Arsenal fan is excited by what lies ahead for the rest of the season, in a sport that has captivated him ever since he saw those first horses point-to-pointing at Bogside in the 1960s.

“There’s so many nice things about the National Hunt scene, from the grooms to the trainers to the people who go racing,” he says. “I take a lot of happiness from this sport. Of course, we’d all like more prize-money, but it’s a great industry.”