Calvin Ayre has come a long way from a pig farm in Saskatchewan to a billionaire playboy life spent partying with rap artists and bikini-clad women in the Caribbean. The son of a convicted marijuana smuggler, he runs Bodog, one of the largest online gambling operations in the world. According to the authorities, the site continues to accept wagers from America where it is illegal to do so. He is in London preparing to target British and European customers.
Within five minutes of welcoming us into his Mayfair hotel suite, Ayre picks three oranges from a fruit bowl and starts juggling, inexpertly. "Did you get that?" he asks the photographer, retrieving an orange from the carpet. "No? Let me try again."
Other wealthy online gambling pioneers prefer anonymity or are fiercely private, on the advice of their lawyers. Many have quickly sold out of the businesses they founded; one or two are languishing in US jails. Ayre, who remains firmly at the helm, believes his showmanship is central to the success of Bodog, one of the largest online bookmakers, with considerable poker and casino operations as well.
It is an approach to business, he explains, inspired by the likes of Sir Richard Branson, Hugh Hefner and even Paris Hilton. "People can make fun of her, but she knows what she's doing when it comes to branding - she has made the Paris Hilton brand."
Ayre's public profile is designed to showcase the trappings of a jackpot-winning lifestyle that could appeal to "people who think like 18- to 40-year-old males". He hosts lavish, well publicised parties in Costa Rica and Antigua for the big-spending customers, with bikini-clad Bodog Girls and armed bodyguards in attendance.
It's a world away from the long, bitter winters of Ayre's childhood on a pig and grain farm in north central Saskatchewan. He talks in near disbelief about his quiet small-town upbringing.
"All through my life it was get up in the morning, go feed the pigs, go to school and come back. It was dark when you left, and dark when you came back. There would be snowdrifts. We would skate on the road where the snow had been packed and frozen. We lived miles out of town so it was completely secluded. At the time, we considered that completely normal. Now, to me, it seems like almost a bizarre existence."
Today a perma-tanned Ayre is the Caribbean-based showman, the most prominent figure in a shady industry. Judging televised pay-per-view lingerie contests during the Super Bowl interval and signing rap artists Wu-Tang Clan to his own recording label are among the many stunts he has pulled. Even his own personal fortune has been on parade, bolstering the image. Two years ago, he was interviewed in a cover story for Forbes magazine under the headline Cyber bookie Calvin Ayre Sticks it to Uncle Sam: Catch Me if You Can.
At the time Ayre - who has since said he was unhappy with those headlines - was riding high, in common with rivals such as London stockmarket-listed PartyGaming, Sportingbet and BetonSports. Bodog handled $7.3bn (£3.7bn) in wagers in 2005, tripling volumes from the previous year. Soaring sales, overwhelmingly from the US, had reached $210m, leading Forbes to estimate Ayre's net worth to be "at least $1bn".
Six months later, the industry was in turmoil. The US authorities had always said unsanctioned online gambling was illegal - a breach of the 1961 federal wire act. In October 2006, new legislation was passed that barred banks from internet wager-related fund transfers. Up to this point, without assets in the US, offshore firms had been able to evade prosecutors, but targeting the payment process transformed the legal landscape.
Overnight, there was an exodus of London-listed firms from their largest, most profitable market. Leading poker group PartyGaming lost 75% of its business while Sportingbet was forced to sell Sportsbook.com, the largest online bookmaker in the world, for $1.
Ayre admits his business shrank for a while, but Bodog did not abandon its US customers. In fact, with many rivals out of the way, the new legislation has allowed Ayre and a few other rogue operators to increase their grip on US punters. "The US government has made it extremely difficult to start operating in that market, chased out most of the well capitalised public companies and created a protected environment for the few privately structured companies, like Bodog and Pokerstars, that had some brand traction already. What's the word for it in economics? - An oligopoly. That's effectively what's going on now."
Last year, Ayre says, Bodog handled £12bn of bets and revenues rose to £320m, though he is coy about how much of this is from US customers. As public companies retreated from America there were opportunities to pick up assets at knock-down prices. "We bought a lot of stuff, some of it confidential so I can't mention it," says Ayre. One of the few disclosed deals was Bodog's $9m acquisition of the entire operations of Aim-listed online bookmaker Betcorp, another US-focused business.
"I was on record, at least three years before the US changed its rules, saying the low-hanging fruit in our industry is the public companies, and if the US government wants to make a statement all they have to do is rattle the bush and the public companies are going to fall out ... Exactly what I said happened. That is why we would never go public."
Ask him how Bodog's activities in America can be viewed as anything other than criminal and the carefully rehearsed answers struggle for clarity under the weight of legal advice that informs them. He admits, before October 2006, Bodog "directly offered services to the US market". On the other hand, he insists: "Our position has always been that we are operating legally in all of the jurisdictions that we are in. And we don't operate in the US."
In response to the passing of tougher US legislation, Bodog struck a "brand licensing" deal with a Canadian Mohawk group based on the Kahnawá:ke reserve in Quebec, already well established as a hub for online gambling targeted at the US. "It's an indigenous group that feel that they've got indigenous [gambling] rights ... They take the Bodog brand and target US customers," explains Ayre.
"My lawyers in the US say I've got no problems, that there's no legal reason why I couldn't go to the US if I wanted to." That said, he makes it very clear he has no intention of testing this advice.
Staying one step ahead of US rules and regulations has been a central preoccupation of Ayre ever since he started up Bodog. The business, which did not truly take off until 2000, was born out of a Vancouver-based dotcom seed capital group owned by Ayre. He fell into the tech world almost by chance after his managed office business became a hub for internet-focused companies.
Before founding Bodog, Ayre was most notable in Canadian business circles for his involvement in a share-trading scandal at Vancouver firm Bicer Medical Systems, which made heart valves. The episode ended in Ayre, who was Bicer's president, being barred from acting as a director of a public company in British Columbia until 2016.
"Some of the stuff I did I didn't even know was a violation of anything, but there were a few things that I knew weren't done exactly right but I was being advised that it was OK to do it that way," he recalls. "Definitely my career since then has been exemplified by attention to detail."
It is not the first time Ayre has come to the attention of the authorities. In 1987, police broke a smuggling operation involved in the importing of 750lb of marijuana from Jamaica to Canada. Ayre's father Ken was sentenced to four years in jail and Calvin was referred to in court by the trial judge as an unindicted co-conspirator who "undoubtedly played a part in this whole scheme or was part of the whole arrangement".
Ayre, who was 22 at the time, emphasises that he was never charged in relation to the episode and had no opportunity to refute remarks made about him at trial by police and the judge.
Ayre concedes that offshore gambling services, targeted at US customers, have historically been exploited by organised crime groups.
But, he suggests, the word "mafia" has been too loosely bandied about, particularly linked to rivals who accept US bets on credit. Bodog has never been involved in such credit betting and has no links to organised crime.
There can be no doubt, however, that Ayre's brazen self-promotion will have raised hackles within the US department of justice and the internal revenue service. He has become an obvious target for federal prosecutors who have in recent years shown their determination to pursue industry leaders. In 2006 there were four high-profile arrests in the US of executives or big investors in London-listed online gaming groups. Since then, no one from the industry has dared set foot on American soil.
The CV
Born Lloydminster, Saskatchewan. May 1961
Education University of Western Ontario, BS General Sciences, 1984; City University of Seattle, MBA 1988
Career 1988-91 Bicer Medical Systems and estate agent, Vancouver; 1991-94 Built and ran HQ Vancouver; 1994 Began work that led to Bodog
Family Named one of "world's hottest bachelors" by People magazine
Hobbies Wakeboarding, hockey, rugby, piloting planes, scuba diving