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He moved to Antigua specifically to get away from the U.S. anti-gambling laws, created the World Sports Exchange, which became a very successful company selling gambling services to Americans, primarily.
NPR: U.S. Slow to Change Internet Gaming Laws
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President Bush wants a new and positive relationship between the American people and the people of Iran a beneficial relationship of increased contacts in education, cultural exchange, sports, travel, trade, and investment.
NPR: In Policy Shift, U.S. May Meet with Iranians
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For starters, professional sports leagues would have to be convinced that a team owner using the exchange in that manner wasn't in effect betting against his own team.
FORBES: Magazine Article
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Betfair, an online-betting exchange based in London, has been called the eBay of sports betting (see article), and the vast majority of the websites that allow people to play poker and other games of chance or skill for real money are based in Europe.
ECONOMIST: Online gambling in Europe