Calvin Ayre: Entrepreneur and Criminal?

Calvin Ayre is an entrepreneur billionaire best known for founding the successful Bodog gambling brand. He cultivates a bad boy/playboy image, but he's a serious business owner with an MBA in management finance from City University of Seattle.

He has been featured on the front page of Forbes, was named one of People Magazine's "Hottest Bachelors," and was named one of Star Magazine's "Most Eligible Bachelors." He's also one of the US Immigrations and Customs Enforcement (ICE) most wanted criminals. Calvin Ayre holds an interesting variety of distinctions, and it doesn't look like he's planning on slowing down any time soon.

Early Life

Calvin Ayre was born in 1961 on a farm in Saskatchewan, Canada. As a child, he got his first taste of entrepreneurship when his father allowed him to raise his own pigs, take them to the market, and keep the proceeds earned from selling them off. He often cites his father as one of his greatest inspirations for success.

When he reached college age, Calvin Ayre attended the University of Waterloo and earned his bachelor's degree in general sciences. He then went on to the City University of Seattle where he earned his MBA in management finance.

He finished his degree and then went to work for Bicer Medical Systems (a heart-valve manufacturer) in 1990. It was during his time at Bicer that he first ran afoul of the law. He was accused of selling 300,000 shares in the company without releasing a prospectus and moving millions of shares around between accounts without filing insider trading reports.

To this day, Calvin doesn't deny those allegations. He says that he knew what he was doing was illegal, but also that he had to do it to keep the company alive. Official charges were never filed against Calvin, but he later settled in 1996. He was fined $10,000 and barred from running a listed company on the Vancouver Exchange for 20 years.

In an interview with the Vancouver Sun, Calvin had this to say:

"I clearly made some mistakes, but it was not a criminal issue and nobody got hurt from anything I did."

And in an interview with Forbes, he said:

"I knew I wasn't following all the rules. But I also knew I had to do it to keep the budget alive."

No problem. Bicer Medical was just a stepping stone for the future billionaire. He later taught himself network design by borrowing Cisco training manuals. He attempted several internet ventures in the early 1990s, but none of those panned out.

The Birth of Bodog

Calvin has mentioned in several interviews that the inspiration for what would later become "Bodog" hit him in 1992. He read a newspaper story about a US bookmaker who had set up shop in the Dominican Republic taking sports bets over the phone from US customers. The bookie, Ronald Sacco, had so far managed to avoid facing charges in the US since he resided out of the States and was operating a legal business where he lived.

Ronald Sacco was later arrested and imprisoned in the US, but the story stuck with Calvin. He said later that he instantly realized how well sports betting and the internet meshed together. Calvin then took $10,000 and put his computer networking knowledge to work and designed software for offshore gambling companies.

Several gambling sites licensed his software, but Calvin knew the big money would be in running his own operation. Calvin Ayre went to Costa Rica in 1996 to get more closely involved in the emerging online gambling business. While there, he saw firsthand the potential in the online bookmaking business. He also saw opportunities to improve on the existing business models of the time.

In 2000, Calvin Ayre was ready to start his own online sportsbook. He landed on the name "Bodog" after deciding that he wanted a memorable, short, and unique name. His sportsbook accepted small wagers from casual bettors and maximum bets as high as $5,000. Payments to and from players were all made electronically through a clever system of banking that routed payments from US accounts to Bodog-owned accounts in the UK.

Bodog started out as a pure sportsbooks, and then later expanded into online poker and casino games. Calvin also carefully cultivated his brand image. He plastered his face all over advertising and welcomed media attention. This accomplished two goals:

1. It lent credibility to the Bodog brand. People knew who ran Bodog and tended to trust Bodog more than other betting sites that were run by people who didn't want their names out there at all. At the time, online gambling was seen as being even shadier than it is now. He wanted to connect with potential customers on a personal level.

2. His image as a kind of playboy always living it up and partying with beautiful women targeted the demographic of the typical 18-49 year old American sports bettor.

With a slick betting interface and excellent marketing campaign, Bodog quickly grew to become one of the most successful online betting sites at the time. By 2005, Bodog was processing more than a million bets per day.

Calvin Ayre didn't stop there. He continued to cultivate his image, bought advertisements in the US, hosted wild events such as the Lingerie Bowl and expanded the Bodog brand into other businesses. He hosted major MMA fights via Bodog Fights and started the Bodog Music record label that signed artists such as DMX and the Wu Tang Clan. He courted celebrities and paid them to attend Bodog-themed events.

It was around this time that Calvin Ayre was featured in numerous major US publications. He was named the hottest or most eligible bachelor by Star Magazine and People Magazine. He made the front cover of Forbes. Calvin later said that this kind of publicity was fun and all, but he really valued it for his business image.

The years 2000 through 2006 were the boom years for Bodog. It became a household name and you could see advertisements for it everywhere. Bodog was hosting fights, producing TV shows, and sponsoring sporting events. Life was good for the people at Bodog.

Bodog hit its first bump in 2006. The United States passed the Unlawful Internet Gambling Enforcement Act (UIGEA) which targeted gambling sites and banking institutions that aided gambling sites. Calvin Ayre decided to withdraw from the US market by licensing his brand name to the Morris Mohawk Gaming Group based out of the Kahnawake reserve in Canada.

Nothing really changed from its customers' point of view, but this move effectively distanced Calvin Ayre from the legally perilous US gaming market. Calvin Ayre later announced his retirement from gaming.

He still kept control of his branding organization, Bodog Brand ( He licensed the name out to other gaming organizations, but Calvin himself was out of the gambling business. The US Department of Justice took an interest in prosecuting Calvin Ayre, but he has so far managed to stay out of trouble due to him not being a US citizen and that he is staying off US soil.

A part of Calvin's strategy has been to carefully segment his business across different countries in order to take advantage of favorable laws. For example, he ran his main headquarters out of Costa Rica where there are no laws against online gambling. He ran call centers in Canada but didn't offer gambling to Canadian citizens. Most of his customers, meanwhile, came from the United States where he didn't have a physical presence at all.

This fractured approach has made it difficult for any one country to bring Calvin in on criminal charges. Here's how Calvin Ayre put it once in an interview with Forbes:

"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."

In 2009, Calvin Ayre announced that he was coming back from retirement. He launched the insider news site and brought back Bodog as a licensing business. He has since licensed the Bodog name to gambling sites in Europe and to products as diverse as coffee and "battle of the bands" contests.

Calvin Ayre: Homeland Security Most Wanted Criminal

It would be funny if it wasn't true. Yes, Calvin Ayre is considered one of Homeland Security's 10 most wanted criminals. The ICE division considers him a criminal for his role in an online gambling conspiracy and money laundering scheme.

Calvin Ayre Most Wanted List

You can see him above (second from left, top row) pictured alongside drug kingpins, international spies, child pornographers, and members of major criminal organizations. The Canadian who started the now-venerable Bodog organization that employs hundreds of people around the globe actually has a spot in the list of the most wanted criminals in the world.

His spot in this list is a result of the efforts of US Attorney Rod Rosenstein from Baltimore. In the February 2012 indictment, Calvin Ayre is accused of running an illegal gambling business from 2005 to 2012 in contradiction to Maryland law.

Calvin Ayre is still a free man and should remain so unless the US suddenly becomes more aggressive in its approach to online gambling. It's a difficult crime to prosecute, because Calvin hasn't violated laws in any of his home countries, and he doesn't actually break US law while being in the US. Things can always change of course, but Calvin Ayre will remain a free man for the time being.


Calvin Ayre is an active philanthropist and has donated significant money and time to projects around the world. He started the Calvin Ayre Foundation in 2005 to go around the world and donate resources, time, and money to good causes.

Some of the projects include helping fund animal shelters, holding a hurricane Katrina relief auction, fighting against illegal bear bile farming, helping kids around the world get educations, and much more. You can read more about CAF's work .