An Entertaining History of In fact, you can get reasonably optimistic odds that online gambling being legalized under Obama. Not since Dick Cheney accidentally drilled a fellow hunter has there gamblihg so much focus on a vice president and a shotgun.roulette secrets uncovered VIRGIN FREE ROULETTE The Obama administration has cleared the way for states to legalize online poker and other forms of virtual gambling with the release of a new. Betting on American presidential politics - and Obama in particular - has spurred an avalanche of online wagers. Since such gambling is illegal. WASHINGTON (Reuters) - The Obama administration cleared the way for U.S. states to legalize Internet poker and certain other online betting.