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He recalled hiring Mr. Brooks 20 years ago, but said his brother-in-law soon left to work with Bruce Bereano, a powerful Maryland lobbyist and longtime friend of the mayor who was at the time a consultant for lottery firm GTECH.

Mr. Brooks later subcontracted with GTECH in Georgia on a venture that ended in a judgment against his company for $1.4 million, according to news reports.

While working in the lottery business, Mr. Manning said his brother-in-law met Lorraine Green, who then headed the D.C. Lottery Commission, and who more recently partnered with GTECH to bid on the D.C. Lottery. He was brought in as an adviser by Ms. Green in 2009 during GTECH’s failed bid, though GTECH officials vehemently denied ever engaging directly with Mr. Brooks.

Ms. Green, a close confidante of Mr. Gray’s who has been involved in his political campaigns, discussed with D.C. Council members during a hearing on the Gray administration’s hiring practices her “close, personal relationship” with Mr. Brooks.

But asked during the hearing about conversations she had with Mr. Brooks about Mr. Brown’s allegations, Ms. Green declined to answer, citing the ongoing investigation.

One source who knows the Brooks family said they saw Mr. Brooks and Ms. Green coming out of a Northwest restaurant as recently as August, as the region braced for Hurricane Irene.

Howard looked like he’d gained weight, he looked stressed out and tired,” the source said, noting that Mr. Brooks was carrying a case of wine.

Ms. Green’s attorney, Thomas C. Green, declined to comment.

Mr. Manning said he had also seen Mr. Brooks working closely with Reuben Charles, director of operations for the Gray campaign and director of Mr. Gray’s transition team.

Howard was always with Vince at the fundraisers I attended in 2010,” he added.

A number of other D.C. politicos reported multiple sightings of Mr. Gray and Mr. Brooks, sometimes in the company of Mr. Brown and Ms. Green, during the 2010 campaign.

One elected official who requested anonymity because of the sensitivity of the ongoing investigation said he saw Mr. Brooks and Mr. Gray together at least a dozen times, and that they were joined by Ms. Green on three or four of those occasions.

Multiple sources told The Washington Times that after a fundraiser during the 2010 campaign season they saw Mr. Gray accompanied by Mr. Brown, Ms. Green and Mr. Brooks at Ben’s Next Door, adjacent to Ben’s Chili Bowl on U Street in Northwest.

Tom Lindenfeld, a government consultant who worked with Ms. Green on GTECH’s failed lottery bid, said he has never seen Mr. Brooks when he wasn’t accompanied by Ms. Green.

Of Mr. Gray’s purported distance from Mr. Brooks, Mr. Lindenfeld said, “That doesn’t sound right.”

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