Online gambling high-flier Calvin Ayre has been on the run from the US government for the better part of a decade. His defiance even landed him on the cover of Forbes magazine once, the lengthy profile inside tauntingly titled “Catch Me If You Can”.
And they will, if they can. For the chase is still on.

Federal prosecutors continue to pursue the Bodog founder’s extradition two years after he and three others—all are Canadian nationals—were indicted by a federal grand jury in the state of Maryland on illegal gambling and money laundering charges in connection with their association with and Bodog Entertainment Group, which also was named in the indictment.
The indictment alleges the company moved at least US$100 million from offshore accounts in Switzerland, England, Malta and Canada to bettors in Maryland and elsewhere, while paying $42 million for advertising to attract US gamblers. The charges landed Ayre on the US Immigration and Customs Enforcement’s “Most Wanted” list, and in a recent filing in US District Court in Maryland, federal prosecutors requested the case be put on administrative hold while they attempt to track him down.
He is believed to be in Canada or Antigua, they said.
Providing gambling over the Internet is a federal crime in the United States under the 1961 Wire Act, which was updated and formalized for the digital age when Congress passed the Unlawful Internet Gaming Enforcement Act in 2006, the year Ayre made the cover of Forbes.
He has denied any wrongdoing and claims to have retired from Bodog and transferred the brand to the Morris Mohawk Gaming Group, an online gaming operation located on the Kahnawake Indian reservation near Montreal. Yet he has reveled in the notoriety and his response to the indictment was to post a video of himself and a fashion model shopping in London’s Savile Row.
The video has since been taken down, according to The Baltimore Sun, which reported on the new District Court filing. 

The Long Arm of the Law 
Prior to UIGEA, the only significant prosecution for illegal online gambling in the US involved an American, Jay Cohen, a financier who started the now-defunct World Sports Exchange in Antigua and was convicted in 2000 and sentenced to 21 months in prison.
That all changed in the summer of 2006 under George W. Bush’s Justice Department when David Carruthers, a British national and former Ladbrokes executive who headed AIM-listed BetonSports, was arrested by federal marshals at the Dallas airport en route to Costa Rica, where BetonSports was based. He later was sentenced to 33 months in prison as part of a plea agreement on charges stemming from BetonSports’ high-profile online gambling presence in the US.
A year after his arrest, BetonSports founder Gary Kaplan, a US citizen, was tracked down in the Dominican Republic, extradited and sentenced to 51 months after pleading guilty to charges that included racketeering.
BetonSports, a company that had raised £54.6 million in its 2004 London IPO and employed 2,000 at its peak, booked US$20.1 million in profit for the 2006 financial year on $1.77 billion in bets. Eight months later, it was out of business. Carruthers was permitted to return to the UK in 2011. The BetonSports domain name was sold last year for $4,900.
The dominoes were falling quickly in the interim, and some of the biggest names in the global online gambling tumbled, including then-London-listed, Gibraltar-based Party Gaming (since merged with bwin), which would shut down its lucrative US poker operation and forfeit heavy fines to avoid prosecution. Payment processors suffered a similar fate, notably NETeller, whose founders, two Canadian nationals, were arrested in New York in 2007 and subsequently freed in the course of negotiations that resulted in a financial settlement with federal prosecutors that nearly sank the company.
The crackdown gathered steam under the Obama administration, culminating in the spring of 2011 with the so-called “Black Friday” indictments of the offshore companies behind PokerStars, Full Tilt Poker and Absolute Poker/Ultimate Bet and their principals on a raft of charges, including racketeering, bank fraud and money laundering.
Absolute/Ultimate Bet and Full Tilt collapsed, the latter forfeiting all its assets to the government, and founder Ray Bitar was arrested. He managed to resolve charges of violating UIGEA and conspiracy to commit bank fraud and wire fraud with a guilty plea that could’ve put him in prison for 35 years. He was fined $40 million but escaped jail because of ill health.
Full Tilt and Absolute subsequently were acquired by PokerStars as part of a $731 million settlement of the criminal and civil charges hanging over it. PokerStars itself was bought earlier this year by Canada-based Amaya Gaming for a whopping $4.9 billion in hopes of restoring it, shorn of its previous management, to the good graces of the regulated US market. So far, to no avail. But it did survive and remains the biggest player in the sector with an estimated 54 percent of the world’s online poker traffic. 
A Deal in the Works?
Bodog, founded in Costa Rica in 2000, was at one point handling upwards of US$7 billion in annual wagers, according to Forbes. Ayre, the son of Saskatchewan farmers, was estimated at the time to be worth at least $1 billion. Along with the Forbes coverage he appeared on People magazine’s “Hottest Bachelors” list and was marketing himself, in Forbes’ words, “as a kind of Hugh Hefner of online gambling”.
But the company was in the cross-hairs of US tax authorities and had been since 2003. Immigration and Customs officials joined the probe in 2006. The company’s moved its US site to a European domain shortly after the “Black Friday” indictments, according to the Sun, and later moved it again. The US domain was seized by federal prosecutors after the 2012 indictment.
In the District Court filing, an assistant US attorney said negotiations were under way with attorneys for the elusive Ayre to resolve the charges, and it appeared this summer that a settlement was close. But that’s been difficult to verify as the feds aren’t talking and no defense attorneys are actually listed in court records. The Sun resorted to gambling industry sites that say high-profile New York lawyers Barry and Stuart Slotnick are representing him. Barry Slotnick declined to comment, according to the Sun.
Last November, Ayre’s personal web site reported that police had raided Bodog Asia’s offices in the Philippines in connection with an investigation into dummy local companies allegedly organized by Ayre to “relocate the base of his world-wide illegal gambling operations,” according to a Philippine news site. Ayre’s site blamed the raid on the former head of the Asia operation, who the site claimed provided false information to authorities after misappropriating company funds.