Playboy Calvin Ayre is The Original Dan Bilzerian

When one thinks of famous playboys of the gambling world, chances are Dan Bilzerian comes to mind first - but he could not be considered the “OG” of that genre by any stretch. That title belongs to 56-year-old Canadian-Antiguan online gambling magnate Calvin Ayre.

Calvin Ayre recently tweeted this picture of himself - as we can learn from his Twitter feed, he visited the ICE gaming conference in London earlier, that is where he returned from to his residence in Antigua and Barbuda where the photo of him in the company of three swimsuit-clad black women was taken.

Looking at that photo one might think it was inspired by Dan Bilzerian’s Instagram account - but in reality, it might as well be the other way around. 

Ayre’s playboy persona developed during the early 2000’s when he regularly held beauty contests under his online gambling company brand Bodog - long before Bilzerian opened his Instagram account. 

The reality show-style competition was popular, gave the Bodog brand a boost and gave Ayre plenty of opportunities to pose with groups of attractive women around him. He was no stranger to celebrity women either: he was seen spending time with Paris Hilton and Shannon Elizabeth in his heyday. In 2007, he made Star Magazine’s "Most Eligible Billionaire Bachelors” list.

An American bookie operating from the Dominican Republic, Ronald Sacco inspired Ayre to get into the gambling business. The Canadian businessman started off in the brand new industry of online sports betting in the 90’s by designing networks for the very first sportsbooks on the web.

"I was pioneering a new industry" - he later said about his early career in a Forbes article.

Bodog, Ayre’s own online gambling site was launched in April 2000 and is still operating to this day. Although it’s not among the most popular sports betting sites, the fact that you can still place bets there is impressive on its own, considering that in February 2012 Ayre was indicted for illegal gambling and money laundering. Ultimately Ayre got away with only a misdemeanor charge for transmitting gambling information for which he was punished by a year-long unsupervised probation and a $500,000 fine. Evidently, the online gambling pioneer was aware of the legal troubles his service can get into in the US, so it was a not a choice of convenience when he set up his company headquarters and personal residence in the small Caribbean nation of Antigua and Barbuda - that, and his Canadian citizenship helped a great deal for him in the criminal case against him.

Recently Ayre has delved into the new world of cryptocurrencies. This is another thing him and Bilzerian have in common, besides the habit of taking pictures with groups of barely dressed women around them - you can find posts about crypto on the Twitter feed of both gambling playboys.

However, Ayre took in Bitcoin advice to the next level: he was appointed Economic Envoy for Technology Development of Antigua and Barbuda, entrusted with the task of finding the best ways of utilizing the new digital currencies for the island nation.