Flash Harry: The outrageous world of Britain's premier punter

Booming, boorish, bombastic – Harry Findlay is the famous,larger-than-life gambler whose legendary wagers have made (and lost) him several fortunes. At Cheltenham this week, he faces the punt of a lifetime. Chris McGrath checks out his form
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Harry Findlay is distraught. After a couple of ales, he wants a proper meal. But the restaurants are all closed, and he is stuck with the burger van behind Bath Abbey. The stained-glass windows are disappearing into gloomy eddies of mist. As he waits, Findlay rings one of his betting partners. "Any wickets yet?" He listens, and swears with casual awe. "And what price now? Better have another 20 on then." The girl preparing his midnight feast probably reckons she knows all about Harry, this big, loud, coarse-grained bloke. Until she sees the size of her tip.

Findlay squeezes into a taxi back to his sumptuous house high over the River Avon, and settles down before the five giant screens on the wall of his office. A grin spreads across his face as Paul Collingwood repeatedly clubs a cricket ball into a grandstand on the other side of the world. It looks like being an exceptional night. He had only gone into town after teasing some £180,000 out of his computer when Liverpool beat Inter Milan in the Champions League; now, having topped up his bet with that £20,000, he has as much again at stake on England's cricketers beating New Zealand in a one-day international. England finish up with 340. There is surely no way back for New Zealand now.

Life is good. Life with Findlay is never dull, but just now he is perhaps at an unprecedented pitch of his existence. With his scathing contempt for the comforts of religion, Findlay is all about the here and now and – for all the daily excitements of his career as a professional gambler – no time, no place, can possibly promise more excitement and stimulation than Cheltenham racecourse, this coming Friday.

In an oddball partnership with a Somerset dairy farmer named Paul Barber, Findlay owns Denman, the audacious challenger to Kauto Star in National Hunt racing's biggest showdown for years. At the 2007 Festival, when Denman won the novices' championship, Findlay backed him to win, to the tune of £1m. From that moment on, he has been gunning for Kauto Star, the champion steeplechaser – and potentially the greatest jump horse of modern times – who will be defending the Totesport Cheltenham Gold Cup on Friday.

Both horses are trained by Barber's tenant Paul Nicholls, but the whole story has been refreshed by the incongruous, exuberant presence of Findlay. It is hard to imagine what other walk of sporting life might ever have brought these men together, the tweedy countryman and the picaresque adventurer. But Findlay has just extracted a commitment from Barber that he will join him in the Kop for the potential forthcoming Champions League quarter-final. "And if he don't give it 100 out of 100, I'll shoot him," he booms cheerfully.

Kauto Star and Denman will be squaring up with a symmetry seldom permitted by the capricious fortunes of jump racing. They are even housed in adjacent stables, and can observe each other in privacy through a grille in the wall. Kauto Star has shown himself unquestionably the best steeplechaser in many years, certainly since Desert Orchid, perhaps since Arkle himself, back in the Sixties. Yet Nicholls and his staff cannot be adamant that he is even the best horse in their care. Kauto Star has already shown just how good he is. But in his rapid journey through the ranks, no horse has even taken Denman anywhere near the limits of his potential.

"The great thing is, they are what they are," Findlay says. "Their personalities, as horses, are very similar to their characters on the course. They were taking pictures of the pair of them the other day and Kauto was all charismatic, flamboyant, looking like the athlete, the superstar he is. And Denman was there, head down, looking like a black bull, snorting, 'Come on! Come and get me!'"

It is precisely the contrast in their styles that emboldens Findlay to believe that Denman can beat Kauto Star. With a steep final ascent to the winning post, after three and a quarter miles, the Gold Cup tends to prove a punishing test of stamina. But last year a slow early pace placed an unusual emphasis on speed in the finish, and Kauto Star barely came "off the bridle" (that is, he needed little encouragement from his jockey). By having his horse ridden aggressively, Findlay believes that Denman can disclose the Achilles heel in Kauto Star – especially, but not only, if the ground this week were to be soft.

"I've said all along that over three and a quarter miles there'll be no excuses from us, even on good ground," he declares. "Over three miles, I think Kauto would be a good thing, even round Cheltenham. But I think there's still a doubt about him truly staying in the Gold Cup. If Kauto comes off the bridle at any stage, we've won. If you're behind us, and you come off the bridle, you're done for!"

Such theatrical exclamations have, admittedly, made some world-weary folk on the racing circuit tire of the Denman circus. But Charles Dickens would not be so prudish. He would sit down, go back over his oeuvre, and ask himself whether he ever stretched a character quite so tautly between reality and caricature.

Findlay was born in 1962 and brought up in High Wycombe. He left school at 16 to work in greyhound kennels for £18 a week. None of his first five jobs lasted beyond a fortnight. "I remember people explaining to me how mortgages work, how pensions work, and thinking the whole world was completely crazy," he says. "I realised overnight how normal people get screwed to the ground. Both my parents were nurses. I looked at their finances, and realised I would never, ever have a mortgage."

The dogs were his first love. He would go every night: Slough, White City, Harringay, Hackney. Retired greyhounds still lope about his house. "I was surviving, without thieving, up until I was 20," he said. "That was no mean feat, especially knowing what I do now, about the injuries greyhounds carry. But I look back in amazement, and wonder just what the bookmakers thought they were going to get out of this teenager?"

None of them proved humane enough to take the lad in hand. In due course Findlay strayed, imprisoned for credit-card fraud. Typically, he now views that experience as an advantage. "In Brixton nick, you don't get too many of the old Pouilly Fuissé, I'm afraid," he says wryly. "I got arrested in the members' bar at Wentworth, stood right next to Nick Faldo and Greg Norman after they'd won the semi-finals of the 1983 World Matchplay."

His life took a new turn 20 years ago, with an £80 treble linking a racehorse, Holland in the European Championships and Stefan Edberg at Wimbledon. He won £11,000, and was on his way. It has been a bumpy ride, however – and always will be. Last year, he lost more than £2.5m on the All Blacks in the Rugby World Cup. Halfway between those two bets came the 1998 football World Cup, when Findlay discovered "a licence to print money" in a new form of football betting, called Asian handicaps.

"I was penniless, 200 grand in debt," he remembers. "I sold the deeds of the house in Sheffield, sold Kay's car. I had about 90 grand to bet with. After five matches, I was 70, 80 grand behind, near enough down to the last bet I could have. But Mum's house was waiting to go next, because I knew I would win. And by the end of the World Cup I had won £2m."

What did Kay, the mother of his two daughters, make of all this? "She's never moaned once in 19 years," he insists. "She comes from the real tough part of Sheffield. I'd met her when I was at the Crucible for the snooker. She served me dinner. I was with Angus Loughran [the BBC pundit], and said to him, 'What price I marry that bird I've never even spoken to?' We didn't get married, because I fell out with the vicar. But we've been together for 19 years. So what a call that was."

No matter how violently the boat lurches, Findlay always seems convinced that he will ultimately reach dry land. "I know I'm going to win," he says. "Gambling's all about knowing what the right price is. If you're consistently getting massively over the odds, you're going to win. Liverpool could have been beaten tonight and it wouldn't matter, because over a lifetime of those bets you are going to win.

"Everyone knows Arsenal are favourite to beat Rochdale. But what price are they? You're a fishmonger, you go to fish market at Aberdeen at seven in the morning, and you're the world's best judge in monkfish, sea bass, squid, and when it comes in you say, 'Right, we'll have two boxes of that squid, two of that monkfish, two of that sea bass, they're the best I've ever seen in my life.' Yeah, great. Right. Now what are they worth? If you don't know what they're worth, your judgement isn't worth a tanner. It's exactly the same with gambling."

Betting without the draw, for instance, he had assessed Liverpool's chance as between 0.65 to 1 and 0.69 to 1. And he was able to back them at 0.9 to 1 (that is, winning 90p for every pound staked). "There's no profit margin like that in copper or any of these other clever things where people make money," he observes. "They're clever – but they ain't as clever as that."

In a way, it is no different from the Stock Exchange. "And my parents would have thought I was a lovely lad, getting on the train into London every morning," he says. "But I would have had my morals ripped out of me. There's no morals in the City." He invokes a well-known betting firm. "They will take your house, they will take you to court, they will destroy everything you stand for. But if you happen to be my next-door neighbour, and I educate you how to bet and you start winning, they will close your account within three weeks. That is morally wrong. And that is what the City teaches you.

"Nowadays, some casinos even have two zeroes on the roulette wheel. Anyone playing them should be certified. But gambling on a Champions League match, a Premier League match, you can win." This, he explains, is because modern betting exchanges take a far lower proportion of their punters' stakes in profit. "There is no margin, it's about 2 per cent.

"If I were leaving school now, the chances of ending up behind bars are the same as me skiing for Britain in the London Olympics. It only happened because of all the lies and kidology that used to go on with betting. Nobody can get [bets] on with bookmakers, because when you win you get closed down. Now it's all up front. We're now living in the real world. Press that button on Betfair and let's see how good you are. Simple. There's no myths or lies any more, it's all fact."

He also believes that direct, accountable trading via the internet betting exchanges is taking the carpet up on the cheats, and he colourfully repaints some of the turf's most honoured names as arrant frauds. "At the end of the day, it don't matter how big your house is," he says. "Nurses and teachers working for nothing, they're the real legends. If you cheat, what kind of buzz is there, conning all that lot?"

A mass betting market can only be sustained by trust, and that is why these are boom years in football betting. "Its honesty and integrity puts the Premier League on a sporting level almost beyond compare, globally," he says. "Everyone knows that if Bolton play Fulham on a Monday night, it's going to be 100 per cent straight. They know that in Indonesia, Thailand, Japan, China, places with a better understanding of mathematics in relation to gaming. And it puts every Premier League game on a par only with the Euros, the World Cup, or the later stages of the Champions League."

And big markets are crucial to Findlay's system, which he succinctly describes as "glory or the bullet". Among the high priests of betting, he is a lone voice in preaching the value in backing favourites.

"The real money is in the short prices," he says. "I know I'm never going to make more than 4 per cent [on turnover] so if I don't bet in tens of thousands, I'm not going to make much of a living. And the only way you can bet real big, in terms of getting on, is on the short prices.

"There are three things people have to understand: a) you can get on; b) you get value; c) you get confidence. And no matter what you do in life, confidence is the number one. Say one fellow bets 20-1 shots. After 20 losers, he backs a winner, and he's level. Another fellow's betting evens. After 10 winners and 10 losers, he's level. They've both got the same money, but he's been right 10 times. Who's going to have more confidence? But nobody talks about confidence, the mental instabilities involved in gambling. And that's what it's all about. It's all about how you perform under pressure, how you perform when it all goes wrong.

"Sometimes it is crushing. That last-minute goal. Good friends have a very small share in what I do, so you know they're hurting too. People trivialise gambling. But to someone else, 20 quid can be just as big a bet as some of these I'm having. Remember, I've done it from both ends. Gamblers lend each other money, we'll do anything for each other. I have read a lot of the great philosophers, and gambling is a very good parody of life. A lot of the rules come out the same."

Later that night, Findlay goes to bed disgusted. England's cricketers have somehow thrown it away, with wayward bowling that allows New Zealand's batsman to ease towards their total. With a few balls to go, he gives up waiting for a miracle and goes to bed, having lost the best part of £200,000.

In the morning, he wakes up astonished to discover that the Kiwis managed to lose their nerve. The game finished tied, and all bets are refunded. Findlay is ecstatic. "I thought I'd done my absolute orchestras," he exclaims. (Orchestra halls. You work it out.) "It's like I've just found 180 grand on the floor. I can't believe it."

I return to his house. There is no stopping him now. One of his many phones is ringing. A friend wants to talk about tonight's football. "There's no one knows Barcelona better than me," he announces. "And there ain't no clue there, 'cause they ain't doing it, they ain't done it for 16 months. I am the greatest judge of football on the planet. I served my apprenticeship, mate. Every ground in Europe. I am in the mind of the Catalans, and it ain't happening. Rijkaard has simply had enough, and the genius, Messi, is clearly unsound."

Findlay is always braced for disaster. Only last week he was scalded when Australia, chasing 222, found a way of losing to Sri Lanka from 107 for 0. And he will never forget South Africa chasing down Australia's 434 in Johannesburg two years ago. "They do get beat, the certainties," he says. "Steve Davis and Joe Johnson. After four frames, Johnson was red in the face, Davis was four-nil up, looking as arrogant and evil as usual. At that stage I'd have bet my life on Davis. I would. 'Davis wins, you get 100 grand; he gets beat, you're dead.' I'd have taken the bet straight away."

There will be no certainties on Friday, albeit that Findlay backed Denman when he was available at bigger odds than now. But nobody on the turf could possibly have a keener sense of the experience, and the privilege. Only its smallest minds could begrudge the big man. "Look at the other top owners in racing," he muses. "No matter how good I am, there isn't anything like enough money in what I do for me to have anything like what they've got. Not that it bothers me. But my money, it's real money. That's why I'm so passionate, because it bloody means a lot."

Harry's holy sporting trinity

Jimmy White

"I was mates with him for 15 years on the snooker tour. Jimmy's the straightest man in the world, a proper, 100 per cent geezer, an absolute diamond. Someone like Rafa [Nadal] can walk about and hardly get noticed, but go and see a movie with Jimmy, at four in the afternoon, and people will come up to him in the pitch black and ask for his autograph. It's like he has an aura. He may not have A-level English, but you go into a bar anywhere, and he knows everyone and everything that's going on. He'll say, 'Come on, let's get out of here, there's gonna be trouble in a minute.' And you say, 'Don't be daft.' He'll make you go, and as you're going out the door, crash. Without question, my saddest moment in any sporting arena was after Jimmy lost the final frame to Stephen Hendry. He probably knew then he'd never win the world championships. I never cry over sport, but I was so cut up as he hugged his daughters."

Roger Federer

"I cottoned on to him very early, the day he played Xavier Malisse on Court No 2 at Wimbledon. But it's luck as well, not just judgement. He beat Sampras in the fourth round – I backed him at 4-1 – but the next day Henman beat him in the quarter-final. Then the next year he got knocked out in the first round, by the big-serving Mario Ancic, so the bookmakers thought he'd gone backwards. The following year he got knocked out in the first round in Paris by Luis Horna – and that's when I knew he was going to win Wimbledon, because he would have the whole two weeks off before Halle. He was 10-1 and I made him about 2-1. So it was the all-time coup."

Tiger Woods

"I've never met Tiger, but I know him better than anyone else on the planet. I spoke to his mum when he was a youngster, and she told me all you could need to know. He's so easy to read, that's the great thing about him – and Federer. Not only are they the best of all time, they speak with the greatest clarity, and the greatest honesty. There's never any ulterior motive. I'm not even sure Tiger's human. Forget what he does on the golf course. At Augusta, they wouldn't let women or black men even up the drive for 50 years. Tiger Woods wins the Masters by 15 strokes and doesn't throw that green jacket in the fire? He's from somewhere else, Tiger – must be. He's the greatest human being on earth. He has never said a single thing wrong. And then you listen to that poncey commentator, Ewen Murray, on the television... The moment Tiger shows any kind of aggression, he says: 'Now, now Tiger.' If Tiger spits, Murray reacts as if he's raped someone."