Calvin Ayre is a self-made man. He has had an entrepreneurial spirit since the day he was born in 1961. From his humble beginnings in Lloydminster, Saskatchewan, Canada, he was allowed to raise his own pigs on his family farm. He would take them to market and keep the proceeds he earned once he sold them.

This love of business carried him through university, where he attained a bachelor of general sciences degree from Waterloo and an MBA in management finance at the City University of Seattle. He moved along to work for Bicer Medical Systems in 1990. He had a spate of unfortunate dealings during his time there. He allegedly sold 300,000 shares in the company without releasing a prospectus and moved millions of shares between accounts without filing insider trading reports.

Ayre doesn’t deny these allegations, and is quoted as saying “I clearly made some mistakes, but it was not a criminal issue, and nobody got hurt from what I did.” His time at Bicer was just a stepping stone for Ayre, as he would move in and out of different ventures throughout the 90s.

During the 90s, Ayre also became fairly proficient at computer networking. He taught himself using borrowed Cisco training manuals. This knowledge would open the door to his soon to be an empire.

In 1992, Ayre was reading a newspaper story about a US bookmaker who had an outfit in the Dominican Republic taking sports bets over the phone for customers in the US. The bookie was later imprisoned for his actions, but his operation stuck with Ayre nonetheless. He traveled to Costa Rica to get some first-hand experience in the emerging world of online gambling. During his time there, he was able to see how the operations worked and where improvements might be made.

In 2000, Ayre was ready to launch his legacy business, Bodog. The online sportsbook accepted small wagers from the casual bettors and maximum bets as high as $5,000. All payments were made electronically through a clever banking system that routed from US accounts to Bodog-owned accounts in the UK.

Bodog began as a simple sportsbook but soon became a many-headed beast, reaching areas like online poker and casino gaming. They are also the sponsor of a mixed martial art fighting circuit. They have even sprouted a music arm to their arsenal, which has signed artists such as DMX and the Wu-Tang Clan.

Ayre unabashedly promoted the site and was more than willing to be the face of the company. He welcomed media attention with open arms. This helped Bodog immensely. Knowing who exactly ran Bodog lent credibility to the company, and made people more trusting of the site. His entourage of young and beautiful women encouraged the male audience he was seeking to get involved in the site.

Ayre was truly a promotional tool. He was featured on the front page of Forbes, was named one of People Magazine’s “Hottest Bachelors,” and was also named one of Star Magazine’s “Most Eligible Bachelors”. He would continue to cultivate his image through shameless promotion, purchasing tv spots and advertising during the Lingerie Bowl.

The years 2000 to 2006 were amazing for Bodog. The company was booming, and they seemingly had the industry cornered. Bodog became a household name, and the advertisements wouldn’t allow you to forget that name. They became ubiquitous, and it was all thanks to Calvin Ayre.

The halcyon days would come to an end for them, however. In 2006, Congress passed the Unlawful Internet Gambling Enforcement Act, which targeted gambling sites and banking institutions that aided those sites. To avoid getting caught, Ayre moved his license over to the Morris Mohawk Gaming Group based out of the Kahnawake reserve near Montreal.

This distanced Ayre just far enough for him to safely avoid prosecution. His customers would continue to be served as they always had been, and he simply moved laterally through the business structure. He would continue to own the Bodog Brand but ceased his involvement with the gambling side of the operation.

By staying in Costa Rica, the United States had no means by which to prosecute him for his dealings with Bodog. Ayre can’t be extradited since he isn’t an American citizen either. The US government has its hands tied when it comes to trying Ayre for his alleged crimes.

Ayre, in an interview with Forbes, put it plainly. “We run a business that can’t actually be described as gambling in each country we operate in. But when you put it all together, it’s internet gambling.” Ayre knows full well that he owns and operates a gambling giant. Unfortunately for the US government, they can’t pin him down for running one.

Ayre is accused by the ICE division of Homeland Security of playing a role in an online gambling conspiracy and money laundering scheme. He is also accused of running an illegal gambling business from 2005 to 2012 in contradiction of Maryland law. He is one of Homeland Security’s Top 10 Most Wanted criminals for that reason. He has been photographed with drug kingpins, international spies, child pornographers, and members of major criminal organizations.

Recently, an indictment has been unsealed against Ayre and three other Canadians for operating an illegal gambling business involving sports betting and conspiring to commit money laundering. His company is also under indictment, and the domain name was seized by federal prosecutors.

The government has been cracking down on all online gambling sites for similar reasons. U.S. operations of PokerStars and Full Tilt Poker were shut down in 2011, and their owners were indicted for operating illegal online gambling businesses.

Specifically, regarding Ayre, he is alleged to have conspired to direct at least $100 million in sports gambling winnings by wire and by check to gamblers, working with payment processors located both in the U.S. and elsewhere. The prosecutors also claim that Bodog caused an unnamed media broker to launch a $42 million advertising campaign between 2005 and 2008 to attract gamblers in the U.S. to the Bodog.com website.

Ayre is defiantly fighting these allegations. In a statement, he made his position very clear on the matter:
“These documents were filed in Forbes magazine before they were filed anywhere else and were drafted with the consumption of the media as a primary objective. 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 charitable projects through my foundation.”

Ayre is, indeed, quite the philanthropist. He has donated significant money and time to different charity projects around the world. These projects include helping fund animal shelters, holding a Hurricane Katrina relief auction, fighting against illegal bear bile farming, helping kids around the world receive a quality education, and many more. The Calvin Ayre Foundation was started in 2005 to go around the world and donate resources, time, and money to good causes.