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Of local or minority business contracting in general, Mr. Peebles said the idea is to afford opportunities to those who are hindered from competing in their areas of expertise.

“That doesn’t mean an accountant gets to run a hospital, or a developer gets to run a tech company in the health care field,” he said.

“Minority business requirements sound good,” Mr. Peebles said. “But they too often end up being a gift to politically connected people. A victory at the election box becomes a victory for a connected friend.”

Some council members ducked The Washington Times’ questions about minority contracting or Mr. Wilmot this week, as the council convened at the Washington Convention Center for its annual retreat.

Muriel Bowser, Ward 4 Democrat who also had a fundraiser held for her at Mr. Wilmot’s house this year, refused to stop to answer a reporter’s questions.

Ward 7 Democrat Yvette M. Alexander, who receives fundraising support from Mr. Wilmot and has been represented by him in two separate ethics challenges in the past year, didn’t answer calls, emails or text messages seeking her input.

Old guard/new guard

The issue of local — or minority — contractors has faced new public scrutiny after controversy involving the D.C. Lottery. Although Mr. Wilmot has denied any “role or interest” in the lottery, numerous factors suggest he is far from disinterested.

Sources familiar with the matter say Mr. Wilmot surfaced as an interested party in 2008, when he escorted prominent local businessmen Robert Washington and Robert Johnson to see Ward 2 Democrat Jack Evans, chairman of the Committee on Finance and Revenue, which oversees the lottery, as the contract went out for bid for the first time in decades.

An internal memo obtained by The Times that was distributed among advisers to Greek gaming firm Intralot, which along with a local partner won the 2008 lottery contract, shows the firm was convinced that Mr. Wilmot also was working behind the scenes trying to “influence” city officials to rebid the contract because of objections to Intralot’s local partner.

Among the Intralot team’s theories at the time, the memo states, is that Mr. Wilmot succeeded in brokering a deal calling for the rebid of the lottery contract. Then, after Intralot won a second lottery procurement, the firm was told that the council would not approve their contract without a new local minority partner.

The message was delivered by Mr. Barry, and the local firm Intralot selected, Veterans Services Corp. (VSC), was founded by Maryland businessman Emmanuel S. Bailey.

While it is unclear if Mr. Wilmot has any business agreements with Mr. Bailey, they are friends, occasional golf partners and frequent political contributors who often favor the same candidates and appear to employ similar business strategies.

Mr. Wilmot, when he is not lobbying for Fortune 500 companies or representing D.C. officials facing ethics challenges, pursues parking contracts and development deals as a disadvantaged local businessman with little staff, no parking lot license and no real business address other than his home or a sub-basement office in a residential condominium.

Mr. Bailey, who, according to the D.C. inspector general, had no lottery experience, operated out of his mother’s home in Southeast, and was appended to the deal after the lottery had been competitively awarded, pursues construction, high-tech and cleaning contracts subject to set-aside requirements at the federal and local levels — that is, when he is not controlling a 51 percent share of Intralot’s lottery contract.

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