Panama Papers: On the Run with Fugitive Gambling Czar Calvin Ayre

Update: Ayre pleaded guilty in July 2017 to a single federal misdemeanor, accessory after the fact to a violation of the Wire Act. He was sentenced to one year of unsupervised probation and a $500,000 fine. Prosecutors dropped all other charges. He also paid $100,000 to reacquire the domain name, which had been seized by prosecutors.

Calvin Ayre poses with women in Antigua in an image posted to his Facebook page

Calvin Ayre poses with women in Antigua in an image posted to his Facebook page

Ayre made the cover of Forbes magazine as the first billionaire impresario of the online gambling world, landed on People magazine’s “Hottest Bachelors” list and took “MTV Cribs” on a long, televised tour of his over-the-top, $3.5 million estate in Costa Rica. Playboy covered his massive birthday bash in Prague in 2010 and called it “a surreal party with a bizarre mix of … European models, midgets and live pigs.”

Click Here to Search the ICIJ's Database

He is always surrounded by fawning women in bikinis, servants offering champagne and caviar, and has armed bodyguards and bulletproof limos at the ready, at least according to his own torrent of promotional videos, news releases and social media that tout his “Play Hard” lifestyle.

"Long Weekend, Antigua Style"

In 2012, Ayre achieved a different kind of notoriety when the U.S. government indicted him and three alleged associates on charges of conspiracy to launder money and illegal gambling, since most on-line gaming is illegal in the U.S. and a huge chunk of Bodog’s customers were American. Suddenly, there was a new photo of Ayre on-line, as one of the Department of Homeland Security’s 10 Most Wanted fugitives.

Four years later, Ayre, 54, is still eluding his pursuers from the Justice Department and the IRS, moving himself and, authorities believe, large sums of ill-gotten gains, from one exotic tax haven to another – and documenting his travels on social media.

“Long weekend, Antigua style,” he wrote in one beach-side May 2 Facebook post with a winking smiley face emoji, two bikinied and beer-drinking women on his lap, his tongue thrust out and both hands raised with the two-finger victory salute. “Opted for some extra leg room on the flight home,” he said on another post last month, with photos of a private jet with red carpet rolled out, and Ayre seated with another beauty on his lap.

In the searchable version of the massive Panama Papers database made public today, Americans won’t find U.S. links to the same kind of bold-face names –- top politicians, athletes and entertainers –- that have surfaced overseas as secret owners of offshore companies used to stash millions in ill-gotten gains, commit crimes or evade taxes.

What they will find is a lively assortment of con artists, scammers and alleged criminals like Ayre who have had accounts at the now-notorious Panamanian law Mossack Fonseca while allegedly engaging in nefarious activities in the U.S.

A review of the law firm’s internal files by the International Consortium of Investigative Journalists and other media partners, including NBC News, has identified companies tied to at least 36 Americans accused of fraud or other serious financial misconduct. Some have been convicted of fraud or other crimes, while others have been sued in civil cases launched by securities regulators or private plaintiffs.

Authorities have put many of the perpetrators out of commission. Some are in prison, or already out after serving their time. Others, like Ayre, are still in the wind, though unlike him they aren’t sending virtual postcards to their pursuers via Facebook.

Over the years, the feds believe they have come close to catching Ayre on several occasions. They have even pursued a negotiated settlement with his lawyer, since Ayre is a Canadian citizen and the Canadian government has made it clear that it won’t extradite him, according to a U.S. law enforcement official familiar with the long-running investigation. A Canadian law enforcement official told NBC News that per government policy, she could not discuss any ongoing investigation into a Canadian citizen including whether authorities have received or can act on a request for arrest or extradition.

Authorities also believe that Ayre and his associates have successfully used layers of offshore companies to hide potentially hundreds of millions of dollars in illicit earnings from them. They are still trying to get their hands on that loot, on top of the $68 million they say they’ve already seized.

And they believe that information from the massive trove of leaked offshore company documents known as the Panama Papers can help them accomplish that. In all, a still-unidentified person obtained 11.5 million documents that comprise the entire client files of one of the world’s largest “offshoring” companies – the Panamanian law firm Mossack Fonseca – and leaked them to the German newspaper Süddeutsche Zeitung, which in turn shared them with ICIJ.

Calvin Ayre's YouTube channel featured an "Ask Calvin" series where viewers submitted questions online to Calvin.

Calvin Ayre's YouTube channel featured an "Ask Calvin" series where viewers submitted questions online to Calvin.

In reams of court documents and seizure orders, U.S. authorities have made it clear that they know a lot about the complex web of offshore companies used by Ayre and associates over many years. The 2012 indictment accuses four of them of moving $100 million from accounts in Canada, Malta, England, Switzerland and elsewhere into U.S. accounts to pay illegal winnings to American bettors, and another $42 million to pay for advertising.

But authorities confirmed that they were not aware of another offshore company that Ayre created in the tax haven of Tortola in the British Virgin Islands, and controlled from 2007 to early 2013. They believe that company and others revealed by the Panama Papers could help them connect the dots between Ayre and potentially dozens of other associates as he expanded his gambling, betting and alleged money-laundering operations to the Caribbean, Europe and Asia and even a Canadian Indian reservation a short drive from the U.S. border.

“Let’s just say we are very eager to see what’s in the documents,” the U.S. law enforcement official said, speaking on the condition of anonymity because of the ongoing investigation. “Any information that would help us … locate accounts, or funds or investments of any kind, is something (authorities) would be interested in.”

“When you look back at the files, you see that [the U.S.] seized a lot of money,” the official said. Asked if he believed Ayre and his associates had stashed significantly more money that is still out there, he said, “Yes.”

NBC’s research suggests that the amount of money could be substantial based on how much money was making from Americans betting on everything from sporting events to card games and even U.S. elections.

$24 Billion in Bets

Ayre himself, always eager to stay in the public limelight, boasted to reporters that his personal net profit was about $55 million just in 2005 alone, based on $214 million in revenue that took in that year. The next year, when Forbes put Ayre on the cover of its annual “Billionaires” edition, he boasted of even bigger earnings. He said Bodog’s business was tripling in volume every year, and that he wasn’t paying personal or corporate U.S. income tax on any of it.

By 2007, as online gambling exploded in popularity in the United States, Ayre stated that Bodog handled almost $24 billion in bets and earned $640 million in revenues, which would mean $160 million in profits based on earlier ratios. He declined to say how much of that was from U.S. bettors. He also boasted that he’d begun snapping up other online gambling-related companies at fire sale prices, including $9 million for a U.S.-focused business, Betcorp. And Ayre had expanded the business into Bodog Entertainment, adding a TV unit, music label, conferences and contests and even a charitable foundation.

The documents shared with NBC News show that many of those individuals in the Panama Papers with a U.S. connection have been accused, indicted or convicted of various kinds of fraud or serious financial misconduct. The documents open a window on how some of these individuals used offshore entities to engage in, or hide a variety of criminal activities, while others used them to move money around clandestinely.

The documents also contain information about how at least two other significant operators in the online gambling world were using offshore companies, although –- as in Ayre’s case –- they do not suggest any kind of illegal or improper activity.

One is Gary Stephen Kaplan, the founder of a rival site called, who pleaded guilty in 2009 to charges related to illegal gambling and racketeering, forfeited more than $43 million and was sentenced to four years in prison. Another is Michael Flynn III, also known as Mickey Richardson, an American who oversaw the sprawling BetCRIS offshore sports gambling operation. He was indicted in April 2010 along with 27 other people in a wide-ranging enforcement action, and was last seen in Costa Rica. Like Ayre, he remains a fugitive.

Efforts to reach both men or lawyers for them were unsuccessful.

In his manifesto last Friday, the leaker said one major reason that he or she leaked the Panama Papers was because so much of the offshore activity “is legal and allowed in this system. What is allowed is indeed scandalous and must be changed.”

The ICIJ has said it has no plans to share the files with law enforcement agencies, providing access to the documents only to specially selected media organizations around the world so they can investigate abuses of offshore entities in their home countries.

But in a much anticipated move, ICIJ today is publicly uploading a searchable version of the Panama Papers database. It will not include the underlying documentation reviewed by NBC News and other ICIJ partners, including company records and emails and other communications. But it will contain basic information such as the secret owners of the more than 214,000 offshore entities found in Mossack Fonseca’s files for investigators, victims, jilted associates and family members and others to search.

And in his manifesto, the leaker announced that he “would be willing to cooperate with law enforcement to the extent that I am able.”

“In the end, thousands of prosecutions could stem from the Panama Papers,” the leaker said, “if only law enforcement could access and evaluate the actual documents.”

Reached through his U.S. lawyer Barry Boss, Ayre had no comment about his dealings with Mossack Fonseca, or the cat and mouse game he has played with the feds all these years. “I think we are going to decline your request for an interview at this time,” Boss told NBC News.

Mossack Fonseca also has strenuously denied any wrongdoing, saying it relies on middlemen that it refers to as its “clients” – bankers, lawyers and other operatives that feed it business – to make sure that people who get offshore companies through the law firm aren’t involved in criminal activity.

Building an Offshore Empire

By the time Ayre entered the online gambling scene in the early 1990s, he had already been banned from the Canadian stock exchange for 20 years for stock-trading offenses, and was also linked to a brazen marijuana smuggling operation that snared his father and other acquaintances.

The son of grain and pig farmers, Ayre (pronounced AIR) launched in 2000, and built the brand aggressively on the carefully cultivated image of him as the embodiment of the flamboyant “billionaire bad boy.”

From the beginning, Ayre also seemed to market himself as something else – a renegade who picked fights with the authorities who were already cracking down on online gambling as fast as its U.S. business was expanding.

Ayre would later tell a reporter his inspiration for an online gambling empire came from a newspaper story about Ronald “the Cigar” Sacco, the U.S. bookie and reputed mob affiliate who set up a similar operation in the Dominican Republic to avoid felony charges in the U.S.

By 1994, Sacco had moved his operation to Costa Rica and pleaded guilty to money-laundering charges that ultimately sent him to prison. Undeterred, Ayre set up shop there too in 1996, working on some of the first online gambling efforts before launching He started with sports betting and then casino games and online poker, taking bets via credit cards and online checks.

In its March 2006 cover story, Forbes opened with the scene of Ayre lounging poolside at his then-new Costa Rica estate, hung over and in a bathrobe, surrounded by servants. By then, his defiance of U.S. law enforcement was already so much a part of the narrative that the piece was titled, “Catch Me If You Can: Calvin Ayre has gotten very rich by taking illegal bets over the Internet.”

Ayre said that what he was doing was legal because of a complex series of financial transactions using advertisers, money transmitters and payment processors on three different continents.

"We run a business that cannot actually be described as gambling in each country we operate in,” he said. “But when you add it all together, it's Internet gambling."

Authorities had a different opinion, a Justice Department official told Forbes: “Online gambling, whether it is located offshore or not, is illegal when it comes to the United States and its citizens.”

But because Ayre –- and his assets –- were safely offshore, Forbes said, “It remains to be seen whether IRS agents could make Ayre pay, assuming they could get their mitts on either him or his money.”

The night after the Forbes article was published, Costa Rican authorities raided his mansion during one of many parties there. Six months later, Congress passed legislation that targeted enterprises like Bodog. It barred U.S. banks and credit card companies from processing payments to online gambling businesses outside the country.

Before that, online gambling proponents like Ayre said they had some leeway because the existing law barring it -- the 1961 federal wire act –- was too vague. The new law prompted some operators to shut down or seek clients outside the U.S., and some big players were even arrested, including one when his plane en route to Costa Rica had a layover in Los Angeles.

Ayre continued to promote Bodog, and even appeared to be doubling down on its stateside business, according to his comments and media reports at the time. "Our position has always been that we are operating legally in all of the jurisdictions that we are in,” he said. “And we don't operate in the U.S."

Just to be safe, Ayre stopped traveling to the United States, as evidence mounted that the feds were targeting him. In 2008, the same year MTV showcased his Costa Rica mansion, the IRS seized more than $24 million from several of Bodog’s alleged payment processors in three separate enforcement actions.

Ayre denied the processors were directly linked to Bodog, but by then, he’d already shifted at least some operations to the gambling-friendly island of Antigua. He publicly announced that he had retired from his position as CEO of Bodog. And he said he’d transferred ownership of Bodog’s North American operation to the Morris Mohawk Gaming Group, which was based at the Kahnawake Mohawk reserve just south of Montreal and ran the new business under the name

But authorities say they think Ayre stayed in the game, and was busy expanding Bodog’s gambling operations into Asia and Europe. At the time, they believe, he and his associates created more and more offshore companies, and moved money in and out of them.

Elegant Step

The documents in Mossack Fonseca’s database pertain to only one of many dozens of offshore entities that authorities say Ayre set up over the years through a complicated web of transactions. They don’t show any wrongdoing by Ayre, as it is not necessarily illegal to have offshore companies.

But authorities who were provided details about the company by NBC News said they raise additional questions about whether Ayre has benefited improperly from offshore tax strategies and whether his interests have been fully disclosed.

“He was setting up [offshore] companies, and he’d set them up and change them quite frequently,” said the U.S. official familiar with the long-running Bodog investigation.

When U.S. authorities seized some Bodog bank accounts in Switzerland and the Cayman Islands, the official said, Ayre and associates moved the money elsewhere.

“There are places like Liechtenstein and Tortola [in the British Virgin Islands] that have secrecy laws and regulations that can protect peoples’ interest in things,” the official said. “People like Calvin have criminal exposure and use these because they want to hide something.”

The Mossack Fonseca documents show that Elegant Step Group Limited was created on Nov. 26, 2007 by Calvin Wilson and Anita Rose Ayre. U.S. authorities confirmed to NBC News that Wilson was a known alias of Ayre, and that Anita Rose Ayre is his sister.

In the documents, Calvin Wilson gave a passport number saying he was a national of St. Kitts but that he resided in the Philippines. Anita Rose Ayre gave a Costa Rica address. They declared that the company itself was based in Phuket, Thailand, even though it was technically an offshore entity with a registered office in Tortola. In an email, one intermediary told another it was designed for real estate purchases in Thailand.

Over the next few years, the documents show, Ayre and his sister would issue various shares in the company, and withdraw or invalidate others.

On May 3, 2008, the company held a shareholders meeting at Portcullis TrustNet in Tortola. According to minutes of the meeting, contained in the Panama Papers, it was attended by the company’s two principals, Calvin Ayre and his sister Anita, and a witness. The meeting had one agenda item: electing Calvin as chairman so that Anita could resign as a company director and transfer her stake in the company – described as one share –- “to the remaining shareholder,” Calvin Wilson.

According to the minutes, “the chairman made a closing statement” and the documents were signed. All told, the meeting lasted 30 minutes.

Shares of Elegant Step were also moved from one entity to another, according to the Panama Papers. In August and October of 2011, all shares of the company were issued to an entity known as Trustco Trust, which in turn was the registered trustee of another entity, the Del Rey Trust. In November 2012, all shares were shifted again to Incom Trustees Limited, which itself was a trustee of a New Zealand trust called Adaman Trust, the documents show.

By then, Ayre had been replaced with employees of the controlling trust. Then, in January 2013, Elegant Step was transferred again, this time to Mossack Fonseca’s British Virgin Islands subsidiary.

NBC News could not reach representatives of Elegant Step or Anita Rose Ayre for comment, but she has been listed in filings and social media as an associate of Ayre’s, including the Calvin Ayre Foundation. She has not been accused of any wrongdoing.

The U.S. official familiar with the Bodog investigation said that kind of shifting of funds was a common practice of Ayre and his associates to stay one step ahead of the law, and the taxman.

They were able to do so, in part, the official said, because the Justice Department and IRS would have to get permission from authorities in the host country in order to seize Bodog accounts –- and the information would always seem to leak out.

“Whenever we got close, and were about to seize something, they would go dark and move the money so we couldn’t seize it,” said the official. “When we forced them to take one [entity] down, they would have two or three other sets of bank accounts that they just would move their money into. For them it was like flipping a switch.”

In one case, authorities traveled to Switzerland to seize a particular set of Bodog funds.

“By the time we got to Switzerland, it moved to Panama and then to the British Isles. But we finally did catch up with [that set of funds]."

In many other cases, the official said, Ayre and his associates moved the funds around so much that the Justice Department and IRS have no idea where some of the cash is, or how much might be stashed away. “He kept things, and operated, in places that were out of our reach,” he said.

Closing In

The IRS Criminal Investigation division began interviewing people associated with Ayre back in 2003, and by 2006 at least one undercover federal agent had opened accounts to place bets at Bodog to understand how it was using various third-party firms to camouflage its U.S. activities, IRS Special Agent Randall Carrow said in an affidavit.

In January 2009, IRS investigators filed more court documents, this time alleging that Bodog used companies on the island of Malta to circumvent U.S. regulations barring payouts to American players.

By then, Ayre was reportedly residing “in various countries in Africa and Asia that do not have extradition treaties with the U.S,” one newspaper reported at the time.

After the 2012 indictment, Ayre denounced the charges via his website as politically motivated, and an "abuse of the U.S. criminal justice system for the commercial gain of large U.S. corporations."

“We will all look at this and discuss the future with our advisors, but it will not stop my many business interests globally that are unrelated to anything in the U.S. and it will not stop my many charity projects through my foundation,” Ayre added.

He has also denied playing any role in any Bodog-related successor firms engaged in illegal gambling, but authorities believe he is still somehow involved.

That’s especially the case due to all of the new variations of the Bodog domain name –- including Bovada –- that have popped up, and the different locations where they’ve been registered, including Europe and Asia.

Philippine authorities raided a Manila location that they said was part of Ayre’s expanding Bodog Asia operation in November 2013. One police official told reporters that authorities thought Ayre would be there, and that the call center was taking illegal bets from international clients linked to the Bovada address.

“Aside from the fact that Calvin Ayre A.K.A. Wilson is one of the most wanted persons in the U.S., we have also gathered substantial proofs that he has been living in Manila for several years now,” the official told reporters. “Local police are now working with the FBI, to get to the bottom of Calvin’s illegal operations.”

In 2014, more than two years after indicting Ayre, federal prosecutors filed papers saying they continued to pursue extradition, but asking for the case to be administratively closed while those proceedings play out.

Meanwhile, Ayre and the three other Canadians indicted with him remain at large. All are believed to be in Canada, at least some of the time. Ayre continues to travel the world, using, his Facebook page and Twitter feed to comment on all things online gambling related.

After the Panama Papers stories were published, one of his frequent contributors to the site gave Ayre’s followers some advice: “Diversify Your Legal Representation” and “Optimize your Risk Management Strategies.”