If you were to ask him yourself, that is, if you could find him in Cuba or Antigua or wherever he's fanning himself with a fistful of $100 bills, Calvin Ayre would want you to know that he is not a fugitive, that no matter what the media or the U.S. government thinks of him, he has broken no laws and thus is not in any way an outlaw, or even a scofflaw. He would tell you this with a straight face, or perhaps an indignant one. But, you know, if you happened to hear that Bodog, the Internet-based gambling juggernaut that he birthed and then nurtured in his image, has been operating in violation of U.S. law, and that the 47-year-old Canadian billionaire could be arrested if he set foot on American soil, and that he lives like some sort of fugitive international playboy ... well, that's okay too.
So which is it? Good question. I hoped to find the answer by meeting Ayre in Macau, where, his publicist said, he would be exploring expansion opportunities for his company. It was late February, a mild month on the South China Sea. Like Hong Kong, Macau is a Special Administrative Region of China, and what makes it most special is gambling. If you like Las Vegas but wish it were smokier and more Chinese, then Macau is your place. In 2006, the city surpassed Vegas to become the world's number-one gaming destination, as measured by dollars wagered. And, says Ayre, "it's just lifting off."
Ayre slipped on a pair of wraparound Ray-Bans as he stepped out of a drab office building near the MGM Grand Macau, a tricolored monument to legalized vice that, from a distance, looks like a glass sculpture you might have found in Liberace's foyer. A silver knot dangled from a chain on Ayre's neck, and his shirt collar lay open to reveal a sizable expanse of hairless chest. He wore a diamond-encrusted Cartier watch and a thick, silver ring on his right thumb — "so I can use my hand in photos and people will know it's me. I learned that from Michael Jackson."
A black Mercedes pulled up and out slinked aspiring actress Zara Taylor, a tall brunette in a tight black dress, designer sunglasses, and 3-inch heels. She kissed Ayre on the cheek in a way that was personal but not intimate. "Feel free to take lots of pictures of her," he said to a photographer. "For your private collection." As he often does, Ayre then laughed at his joke. It's a laugh that comes fast and lingers long, sometimes uncomfortably so.
"I don't actually have a girlfriend," Ayre clarified, as we pointed the Benz toward lunch. (Taylor had been relegated to a second car.) "That's a hassle. It's the same reason you don't pack your car in the suitcase." Translation: Why would you? Have you ever arrived at a destination and found it to be lacking in cars?
Ostensibly, Ayre had come to Macau for the sixth annual Asian i-Gaming Congress and Expo, which was being held at the new Venetian hotel, the second-largest building on earth. The idea was that he would size up the competition, nibble some canapés, and attempt to get a handle on just how Bodog was going to infiltrate the emerging Asian market.
Between slurps of shark-fin soup at the Grand Waldo Hotel, a Chinese casino near the Cotai Strip, Ayre chuckled at my aversion to a dumpling that resembled a tiny deep-fried hedgehog. He said that I should try partially gestated duck egg, which I assumed was a joke but in fact was not — it's something he eats whenever he's in Bangkok. From here, conversation ponged around like his life: to Bodog headquarters in Antigua, where Ayre has a house; to Costa Rica, where Bodog formerly had its headquarters; to Russia, where he staged some fund-raisers to combat bear-bile farming, a pet cause of his charity, and then threw a massive mixed-martial-arts event that drew both Vladimir Putin and Silvio Berlusconi (as well as Jean-Claude Van Damme); to England, where he recently launched Bodog U.K., and where he went wing-walking, which involves being strapped to a post atop a 1932 biplane flying at speeds up to 150 miles per hour.
Ayre painted a picture of a single man's dream life — all women and wine and limitless cash, where the entire planet was his playground. He was going to take Bodog global by partying from pole to pole, hurdling legal obstacles without spilling his martini.
Or so it seemed. Two months later he'd be gone.
Perhaps you know Bodog because you play online poker or place sports bets, or because you've been bludgeoned by its gonzo marketing, such as the Lingerie Bowl, which counter-programmed the 2006 Super Bowl halftime. It is one of the few major i-gaming companies based in the Americas to have survived, let alone thrived, following a series of legal roadblocks erected by the U.S. government in the past seven years (more on that later).
The company's history has become something of an industry legend. Calvin Ayre, son of a Saskatchewan farmer, who showed up at school "with pig shit on my shoes," was kicking around Vancouver in the mid-1990s, going from one failed Internet startup to another, when he read a story about a bookie named Ronald Sacco (aka the Cigar). The Cigar had done an end run around the law by setting up shop in the Dominican Republic, where he was taking bets by phone. The story served as Ayre's epiphany, as it did for many in the industry after the Cigar bragged of his lush life on 60 Minutes (an excess of candor that would later lead to his arrest). Ayre recognized that the nascent offshore betting scene was gravitating to the Web, and he saw an opportunity. He invested $10,000 to buy an existing software platform, then moved to Costa Rica in 1995 and began supplying software solutions to bookmakers before realizing he could make more money taking bets himself.
Ayre hung out his own shingle in 2000 and began building what would become one of the world's best-known online-gambling sites on the back of a ridiculous name: Bodog. What does it mean? Nothing, actually. Ayre just wanted a name that was easy to remember, fewer than six letters, and vague enough that it didn't suggest a specific product or industry. He says he knew from the start that Bodog would expand beyond gambling, and that to name his company something simple and clear like his competitors — Sportsbook.com, say, or BetonSports — would constrain the sweep of his vision.
Ayre saw his business as an e-commerce venture that sold gambling, rather than a gambling operation that just happened to be online. Internet casinos typically license software and then cough up 10% to 25% of profits to the developers, but Bodog's proprietary platform allowed for higher margins and thus more attractive odds for bettors. Ayre also emphasized customer service and swift processing of payments, neither of which was exactly a strength of the bookies-in-exile who made up much of his early competition.
But what Ayre did best was marketing. Instead of lying low and counting his dollars quietly, he plastered his face all over Bodog's Web sites and tied the brand to his own lifestyle. Collaborating with his friend Christopher Costigan of Gambling911.com, a popular industry news site, he created a public alter ego, Cole Turner the CEO, and faked elaborate adventures that Bodog users could follow online. There was a 2003 party excursion to Cambodia pitched to the Web audience as an expedition gone awry, involving hookers, terrorists, opium smugglers, and, ultimately, Turner's kidnapping. Ayre dressed hotel employees as gun-toting rebels and posted the photos. At least one concerned customer phoned to plead for the release of Bodog's beloved faux CEO.
"I said, 'Man, it's kind of embarrassing, but I'll do it,' " Costigan recalls. "I remember people asking if it's really happening. I'm like, 'Are you kidding me? You actually believe this stuff?' "
In 2004, Ayre outed Turner, then picked up the old boy's fedora himself, flaunting a playboy lifestyle under his own name and modeling himself after his two idols, Hugh Hefner and Richard Branson — hiding nothing while exaggerating everything. "There is no personal in my life," he told me.
Ayre posted photos, videos, and blog entries from his bachelor pad in Costa Rica, where he threw wild parties overstuffed with bikini-clad women who jiggled around in the pool. He bragged of a bulletproof Hummer and a team of "snipers" assigned to protect him.
"[My customers] don't dream of being boring — that's not who they want to be," Ayre explained. "I think of it like James Bond. You're soaking up a little of it. You're a voyeur. There's a bunch of people who know they'll never be me — but that doesn't mean they don't dream about it."
Business boomed. Bodog showed 100% growth its first two years. By 2005, according to Ayre, the company was processing more than $7 billion a year in wagers, pulling revenue in excess of $200 million.
Ayre began diversifying. He filmed his own poker tournaments, and Calvin Ayre Wild Card Poker debuted in 2006 on Fox Sports Network and Bodog TV, his Web-based channel. He added a sports and entertainment Webzine; a music label that distributes artists such as the rapper DMX and the platinum-selling punk act Bif Naked; a million-dollar Battle of the Bands competition that drew more than 7,000 bands in its first season; and an international mixed-martial-arts series called Bodog Fight that is staged in arenas, broadcast on cable in the United States, Canada, and Russia, and sold on DVD. The entertainment properties may never turn a profit, but even as loss leaders, they amplify the brand. "All roads," Ayre told me, "lead to Rome."
Last year, the company claims, Bodog processed $12 billion in wagers and drew revenue of $320 million. Forty percent of the business was casino games; 30% poker; 20% sports betting; and 10% the various entertainment properties. As of March of this year, a company rep told me, Bodog employed several hundred people, including 15 bookmakers, at its Antigua headquarters (where it relocated in 2006), plus a few dozen in the U.K. and between 100 and 300 in Vancouver. The Ayre I met in Macau was feeling bullish. "I sell to people like me, who like what I like," he told me. "If I like it, there's a whole bunch of other people out there who like it too."
A real-world casino is by its very nature perspective-altering; it is engineered to make its patrons forget space and time. By even the grandest of Las Vegas standards, the Venetian Macao is a monster. Forget the gaming floor and hotel; we struggled to navigate the convention center, a labyrinth of oriental-carpet-lined halls that could easily accommodate freight trains. "I want a golf cart," said Ayre, as we made another wrong turn.
Bodog's biggest international move so far was the soft launch of Bodog U.K. in December, which was intended as a wedge into the mainland European market. But Bodog wasn't yet in Asia — a tougher nut to crack, given its more restrictive governments, alien alphabets, and significant cultural hurdles, not the least of which is a prevalent distrust of machines among the Chinese, according to Macom, a Macau-based consulting firm hired by Bodog.
"What we're really focused on right now is Europe," Ayre said. It's an odd thing to say in front of an i-gaming expo in Macau. But it was slowly dawning on me that maybe Ayre didn't really care about the conference, or even Asia; for him, it was just a colorful setting for this story. Once we finally located the expo, with a hundred or so attendees clumped about talking shop, Ayre almost immediately looked bored.
"You'll see three things at a show like this," he said, as he returned from the bar with a glass of white wine for each of us. "Software providers, payment solutions, and licensing jurisdictions." Licensing jurisdictions — countries and territories that permit online-gaming companies to set up shop on their turf — are crucial to the debate about the legality of i-gaming in the United States. Uncle Sam maintains that foreign businesses must pay taxes on business conducted here. Online-gambling operators insist that their business is being conducted not in America's living rooms but on the companies' servers, wherever they may be. If a poker game has a player in Australia, a player in Spain, and a player in Cleveland, and the game is running on a server humming away in a climate-controlled closet in Malta, for example, who has legal jurisdiction? In Bodog's case, the licensing jurisdictions are Antigua and Kahnawake, a Mohawk Indian reservation just outside Montreal that holds the servers of Bodog North America, under an agreement with the Morris Mohawk Gaming Group, a tribal company run by a former Olympic-gold-medal-winning kayaker named Alwyn Morris.
The U.S. government remained mostly quiet during i-gaming's formative years, and operators based outside of the country happily did business with American customers, taking their money, via credit cards, wire transfers, and online services such as PayPal, without paying taxes. But as the industry grew and became more visible — and as a number of companies went public in England starting in the late 1990s — the Department of Justice grew agitated. Citing the 1961 Federal Wire Act (a relic of Bobby Kennedy's anti-Mob crusade that forbids anyone from taking bets over the phone), the DOJ began to pursue online-gaming shops.
The first major conviction was of Jay Cohen, of Antigua-based World Sports Exchange, in 2000. In 2002, Eliot Spitzer, then — attorney general of New York, went after PayPal, which paid a fine and ceased servicing sites in the United States. Next up were publishers who carried online-gaming ads. Sporting News had to fork over $7.2 million, and Esquire was served a subpoena in 2005 over a Bodog-branded ad.
The death knell for many operators was the 2006 Unlawful Internet Gambling Enforcement Act (UIGEA), which punished financial institutions for processing online-gambling transactions. The UIGEA scared away the credit cards, as well as the public i-gaming companies, most of which were traded on the London Exchange. But it turned out to be something of a boon for Ayre, who had decided to keep Bodog private, and thus less transparent.
The year before the UIGEA was passed, the online "gross gaming yield" — what the customer loses — was $14.6 billion, according to the U.K.-based Global Betting and Gaming Consultants (GBGC). Their 2007 estimate was $15.2 billion. In other words, major sites vanished, but the overall volume of play was barely affected. "Some of the really big independent sites such as Bodog and PokerStars boomed after UIGEA because they stepped into the shoes of those who turned their back on the U.S. market," says Warwick Bartlett, a partner at GBGC.
The UIGEA did come at a cost to Ayre's personal life, however. Once a fixture in the clubs of Los Angeles and Miami, he hasn't been back to the United States since the law turned up the heat. His lawyers advised against it, particularly after the arrests of David Carruthers and Peter Dicks, British executives for the public firms BetonSports and Sportingbet, respectively, both picked up at U.S. airports during stopovers in the summer of 2006.
"Everyone in the industry assumes that they could be on some kind of federal wanted list," says Sue Schneider, founder and publisher of Interactive Gaming News. "Calvin Ayre is on a list somewhere," says Frank Catania, the former director of the New Jersey Division of Gaming Enforcement and now a prominent industry consultant. "If he traveled in the U.S., he'd be picked up."
Ayre the optimist, of course, insists otherwise. He told me in Macau that there's no reason he can't come back to the United States, that his company is entirely legal, that he simply refocused overseas. "We voluntarily left that market. Remember, I'm not American. I don't do any business there. There are a lot of countries I don't go back to. I haven't been to Mongolia in the last two years. I haven't been to Chile in the last two years."
But the United States is, after all, more than half of the global online-gambling market. I wanted to hear him say it bothers him, that he misses the United States — the place that made Calvin Ayre into CALVIN AYRE!
"The U.S. is really just not something that we're focusing on right now," he said, "because we don't see that as our future. We licensed the brand rights to an indigenous group [Morris Mohawk]. To us that was, like, a masterstroke. We can walk away operationally but still have an income stream from the brand penetrations that we put in place."
While Ayre insisted Bodog hasn't broken any laws, he also has embraced his fugitive reputation. "It really amps up my bad-boy billionaire stature," he told me. "It gives me street cred."
We lasted maybe a half hour at the Macau convention, not moving more than a few feet from where our entourage first stalled, alongside a booth advertising a mah-jongg site. "I don't actually run anything anymore," he said as he drained his glass of wine. "I'm just high-level direction at this point. You have to let go of stuff, right? Otherwise, you'll die."
It was 7 p.m. at the MGM hotel's Caviar Bar, and Ayre had declared it too early for champagne. Anticipating a long night, he also thought it too early for vodka, so he insisted we should chase our caviar with chardonnay. The marble-floored, gold-walled room was ours alone, but to note that is deceiving. Present were a photographer, a cameraman, a publicist, an assistant, and a stunt girlfriend. It was like a film production of a night out.
Ayre, wearing a satiny white button-down, plopped some caviar on a blini and topped it with sour cream. "Work, work, work, work ..." he said for the first but not the last time.
Caviar was followed by Cantonese food served by beautiful Chinese women (in a private dining room, of course), after which we made a short hop to Cubic, a private club atop an already exclusive club atop an office tower across from the Grand Emperor, a Chinese casino with a giant flashing neon crown.
"The last party was so good that I woke up across the bottom of the bed with no clothes on," Ayre told me. "Alone!" For all of his flaunting of women, Ayre appeared to spend each of his nights in Macau alone. Zara Taylor played the part of the girlfriend, but was actually sharing a room with Fawn Labrie, Ayre's personal assistant and Taylor's childhood best friend. That isn't to suggest that Ayre has any problems with the ladies — one story at Gambling911.com claims he has bedded 8,000 women — but rather that not everything you see in James Bond movies actually happens.
Scattered around the room at Cubic was a smattering of industry friends. Hip-hop boomed from the sound system, and booty-shaking music videos filled the flat-screen TVs on the walls. Objecting to a lack of females in the room, Ayre yelled, "Where the dancing girls at?" as he poured glass after glass of Dom Pérignon for anyone whose glass was even half empty.
At 11:30, they arrived — a line of Chinese models.
"Hello, sexy girls!"
Ayre told me that he had instructed Labrie, who passed the buck to a local contact, to find models who spoke English, because at the last party he threw here — two nights earlier — it was hard to do much more than smile in awkward silence. I told him that before I'd arrived, his publicist had told me, via email, that one of Labrie's skills was the ability "to pull hot girls out of her ass anywhere in the world."
"Fawn gets it," he said. "It isn't sexist. Guys will be guys. How much would this party suck without girls?"
Then, for the better part of four hours, Ayre smiled, danced, smoked the occasional cigarette, and drank champagne. He was in his element, building the Bodog brand. Was he having fun or acting? Is there even a difference?
And that was the last time I saw Calvin Ayre, an apparently happy man about to jet off for Thailand and planning to invade Cannes for the film festival in May with a string of flashy publicity stunts. Two months later, I received the following email from Susan Mainzer, his publicist:
As of 5 p.m. today, I am no longer with Bodog. Be psyched, you probably got the last ever Calvin Ayre interview, see attached.
The accompanying press release, dated April 18, read like a sample letter from the Textbook of Lawyerly Obfuscation:
Calvin Ayre, the internationally noted billionaire playboy founder of Bodog, will be retiring from his largely ceremonial role as the face of Bodog. Additionally, he will no longer be involved in Bodog operationally. In mid-2007, he successfully transferred ownership of the Bodog brand in North America to the Morris Mohawk Gaming Group... . Ayre will be taking some time to himself in his home in Antigua and will continue to support charitable opportunities through the Calvin Ayre Foundation.
One thing that stood out was the phrasing of Bodog's ownership change. Up to this point, Ayre had always explained the association with Morris Mohawk as a "licensing" arrangement, but his farewell missive stated that he had "transferred ownership."
When I checked back with Bodog's Web site, the links to Ayre's blog and foundation had vanished from the top of the home page. But if you backdoor your way in — by typing calvinayrelife.com — you can still see his final blog post: "You've likely heard the rumblings and rumors...I'm packing it in!"
It's an appealing exit story, especially if you're a member of the cult of Ayre. You go, bro! Take the money and run! Yet only a few weeks prior, for April Fools', Ayre had put up a trailer for his "upcoming" reality show, Calvin's Heir (in which nine women supposedly impregnated by the mogul compete to deliver his successor). Why continue to pull stunts like that if his retirement was imminent? And why would he have dragged me to Macau to create a story about him leading Bodog's charge abroad? Surely he would have preferred to exit in grand style. A bungee jump from the Eiffel Tower, say, followed by a party at which 8,000 naked Brazilian girls assemble to form the Bodog logo, visible from space.
I dialed Mainzer's cell phone, and it forwarded to the desk of Greg Godden, the director of PR for Morris Mohawk, in Kahnawake. "All I know is what's in the press release," he said. Ayre would be unreachable from this moment forward, he added, and Alwyn Morris was also unavailable.
When I finally reached Mainzer, Bodog's publicist confirmed that this was no hoax — even she'd been blindsided. "We were planning our next adventures in Cannes," she said.
Mainzer suggested the abrupt change might have been related to some difficulties Bodog had been having with its English gaming license. The implication: Ayre's high profile was giving the British Gaming Commission pause in the application process.
Christopher Costigan of Gambling911.com, Ayre's coconspirator in the days of Cole Turner, was equally surprised. Ayre had called him from Cuba, Costigan said, to break the "retirement" news. Bodog's marketing department, too, had called — in the middle of the night — with a demand that he remove a section of his site devoted to Ayre because it gave the appearance that Ayre wasn't really quitting. "I don't know what to think of it," Costigan told me. "Something must have happened. I didn't see this coming. I'm not buying it." Costigan said that he could only speculate, that maybe Ayre "got tipped off" that some sort of legal action was afoot. He explained that industry insiders were reeling over a recent incident that did not make the news: A well-known i-gaming bookmaker named Rick — there is only a first name — had gotten arrested in Panama while attempting to renew his U.S. passport. Costigan said that Ayre mentioned that it had "nothing to do with Rick," which of course made him think that maybe it had a lot to do with Rick. "I think there's a concern that they can get you just about anywhere," Costigan told me.
I called I. Nelson Rose, one of the preeminent experts on gaming law, who has advised Ayre in the past, and floated a theory: Maybe Ayre was taking one for the proverbial team, allowing Bodog to move forward in the U.K. and beyond by sacrificing himself.
"That's very, very possible," Rose said. "And probably makes more sense than any other theory."
Regulatory change is gaining momentum in the United States. California is moving toward approving intrastate online poker, which would set a powerful precedent. And on April 26, Representatives Ron Paul and Barney Frank proposed a bill to roll back enforcement of the UIGEA and eventually institute a national policy of regulated online gaming. "Although I personally believe gambling to be a dumb waste of money," Paul said, "American citizens should be just as free to spend their money playing online poker as they should be to buy a used car."
If Bodog were ever to hope to participate freely in a regulated U.S. market, it would almost certainly have to do so without Ayre in the picture. Two comparable sites, PartyGaming and 888.com, are known to be negotiating with the United States, the idea being that they will pay huge fines to clear their names. In those cases, the founders have already stepped away.
The industry's market size has grown from zero in 1990 to somewhere in the neighborhood of $15 billion in annual revenue. By 2010, says Martin Owens Jr., another prominent industry lawyer, it will be "at least $20 billion, and that's not including cell phones," which could be i-gaming's killer app. Internet gaming is legal in the U.K. and Australia and chunks of Asia. The E.U. and the WTO both support widespread regulation. The United States, eventually, will get in line, which would open the doors to not only the casino giants — your MGMs and Harrahs — but also the giants of the Web.
I thought back to something Ayre had said — in jest, I thought — in Macau: "Can you imagine how much moneywould make if they rolled out their industry-leading suite of casino games? Or You wanna give me a nightmare? Just tell me that's going to happen. I will retire tomorrow. I'll be a full-time partyer. I'm gonna go pro."
Maybe he is partying full time, or really will resurface soon to focus on his foundation, building schools and combating bear-bile farming from his Caribbean compound. Whatever the case, he's doing it quietly for now. Peter Gold, the general manager of the handicapping site VegasInsider.com and a close friend of Ayre, relayed a message to Ayre in mid-May that I had been asking around. Ayre's blithe reply: that he had been planning to leave "for years" and that he was just "hanging out, chilling." And that he'd be back — but "not for a couple of years."
Sue Schneider, of Interactive Gaming News, who has known Ayre since the mid-1990s, sees a grimmer future. "The DOJ continues to go after founders, even those who are out of the business," she told me. Leaving the picture "is not going to insulate him — at all." (A DOJ spokesperson wouldn't confirm that or comment on Ayre, except to point me to existing case law.)
I reminded Schneider that until the end, Ayre was swearing he'd broken no laws, and that he was living happily ever after.
"That attitude is a little passé. He can think he's safe," she said. "But he's not."
Josh Dean is a freelance writer and infrequent gambler based in New York. This is his first Fast Company feature.
A version of this article appeared in the July/August 2008 issue of Fast Company magazine.