RightChange.com’s blitz of anti-Obama ads has been bankrolled mainly with more than $5 million from pharmaceutical executive Fred Eshelman. But this month the 527 organization diversified: it put out a new ad (below) supporting Republican Sen. Elizabeth Dole in its home state of North Carolina. And it reported receiving $100,000 from a controversial businessman named R. Craig Estey.

In trying to figure out who Estey is, we found some interesting background. Estey runs a chain of gambling parlors in Nevada called Dotty’s. He also operated one of the biggest video gambling operations in Oregon until the state lottery ran him out of town.

In December 2006, Oregon Lottery Director Dale Penn wrote Estey to terminate his state lottery contract because “you do not satisfy the requirements of good character, honesty, and integrity that apply to all Lottery Retailers.”

It all started with a domestic dispute Estey had in 2005, when he allegedly held a gun to his then-wife’s head and threatened her life.

Gaming officials from Nevada looked into it. The Gaming Control Board said that Estey initially lied to its investigators before admitting his wife’s version of events. He eventually agreed to a $200,000 fine from the Nevada Gaming Commission.

The Oregon State Lottery eventually found out about the case from a newspaper columnist. Because of the incident, the lying and the fact that Estey didn’t notify Oregon officials of his problems, Penn wrote that “your continued association with the Oregon Lottery poses a threat to the actual or apparent integrity, fairness and security of the Lottery and is not consistent with the public interest, convenience and trust in keeping with the sensitive nature of the Lottery.”

We tried to contact Estey through his lawyer on Wednesday but Estey hasn’t responded. He sold his Oregon company last year but is still operating in Nevada. And now, Estey is venturing into the not-quite-ended 2008 campaign.

View ads from RightChange here.

This originally appeared on The Secret Money Project Blog, a joint project of CIR and National Public Radio tracking the hidden cash in the 2008 election.

Will Evans is a senior reporter and producer for Reveal, covering labor and tech. His reporting has prompted government investigations, legislation, reforms and prosecutions. A series on working conditions at Amazon warehouses was a finalist for a Pulitzer Prize and won a Gerald Loeb Award. His work has also won multiple Investigative Reporters and Editors Awards, including for a series on safety problems at Tesla. Other investigations have exposed secret spying at Uber, illegal discrimination in the temp industry and rampant fraud in California's drug rehab system for the poor. Prior to joining The Center for Investigative Reporting in 2005, Evans was a reporter at The Sacramento Bee. He is based in Reveal's Emeryville, California, office.