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Neither Ms. Green nor Mr. Gray returned calls for this article.

The Gray insider who put out the word about Mr. Gray’s preference for Ms. Green on the lottery deal reportedly was superlobbyist David W. Wilmot, a fixture in local business and politics for the past 30 years and a former attorney for Mr. Barry. Mr. Wilmot had other friends interested in the lottery.

In December 2008, as Mr. Gray held up a vote on the lottery contract awarded to the local company he did not want and after Mr. Gray had met privately with Mr. Bailey and Intralot’s lobbyist, Mr. Wilmot and Mr. Bailey were among a group of D.C. businessmen on a holiday golf retreat in Hilton Head, S.C.

Multiple sources familiar with the retreat and documents obtained by The Times show that Mr. Bailey made representations at that time to others that he was in a position to bring the lottery to a vote with Mr. Gray’s support.

Mr. Wilmot denies any involvement with the lottery. He confirmed being in Hilton Head in December 2008 but denied meeting with Mr. Bailey, whom he called “a friend.”

A longtime political adviser to Mr. Gray, he co-hosted the council chairman’s first mayoral fundraiser in April. He also hosted a fundraiser for Mr. Fenty in October - the same month the city sued his nonprofit organization, Individual Development Inc.

Individual Development drew fire last year when the city sought to put two of its homes for developmentally disabled people into receivership. The Post revealed that Mr. Wilmot and fellow organization board members Frederick D. Cooke Jr. - also an attorney for Mr. Barry - and A. Scott Bolden - a Barry fundraiser and former head of the D.C. Democratic Party - approved loans to other board members and that Mr. Wilmot drew a lavish salary that raised eyebrows in the nonprofit sector.

Three residents of the homes died in recent years as the city halted referrals as a result of “systemic” problems, The Post reported. Individual Development is under a third-party monitoring arrangement through 2010.

Another D.C. fixture with a mixed track record, former council member H.R. Crawford, also could have the mayor’s ear if Mr. Gray is elected.

Mr. Crawford, one of the more frequent visitors to Mr. Gray’s office, according to the chairman’s desk calendar, has wielded power in the District for more than 30 years, serving as a council member from Ward 7 for 12 years. He also was Mr. Gray’s pick to head the Metropolitan Washington Airports Authority.

A politician turned developer, he has defended gentrification as an opportunity to expand the city’s tax base for the benefit of lower-income residents. But as The Post said in a 2008 article, he has been accused of taking government money to build condominiums that drove out lower-income residents who couldn’t afford the housing.

Between 2003 and 2008, The Post said, Mr. Crawford’s company received $8 million from the city and tens of millions more after he partnered with larger developers without completing any of the development projects.

HUD also accused him of using the money to finance his own property-management firm while collecting millions of dollars in developer fees, a practice officials described as double billing.

In the process, the report said, Mr. Crawford gave out contracts to companies with ties to the government and sold refurbished properties to city officials, employees, relatives and real estate investors known as “flippers.”

Mr. Crawford was fired from HUD in the 1970s for seeking contracts from housing agencies that received money from the department. He was investigated by a federal grand jury when, as a council member, he was suspected of misusing city funds. One of his aides pleaded guilty. Mr. Crawford was not indicted.

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