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By the time the city government finally sought the council’s approval nearly five years after the contract was first approved, the city already had paid out about $6 million.

It was one of several contracts at the time, including several with no ties to Mr. Thompson, in which city officials said they paid vendors too much money without getting the required approvals.

In a request by Mr. Williams‘ office to approve the payments retroactively, city officials explained, “Due to an oversight in administration, option year one was not exercised and the contract expired on March 14, 2001,” records reviewed by The Times state. “After the contract expired, the [Office of Contracting and Procurement] mistakenly awarded task orders to [Thompson Cobb Bazilio and Associations] in the total amount of $6,830,127.27, and TCBA continued to work without a written contract until March 14, 2005.”

Revolving door

After the disclosure that the health care clinic wasn’t open 24 hours a day, seven days a week, several D.C. Council members, past and current, raised questions about the deal, including Mrs. Schwartz. But Mr. Thompson never publicly addressed the criticism, relying instead on longtime associate John L. Ray, an at-large Democrat on the council from 1979 to 1997 and now a lobbyist, to explain things.

Mr. Ray is just one of a number of people who have spun through the revolving door between the city government and businesses tied to Mr. Thompson over the years.

Francis Smith is another. He was the executive director of the financial control board and signed off on the preliminary clinic contract with Mr. Thompson just before the control board suspended its operations after six years overseeing the city’s budget and spending as mandated by Congress. Later, Mr. Smith went to work for Mr. Thompson’s health care company. He denied any conflict of interest when the deal surfaced years later.

James Christian, who was chief operating officer at the city-funded D.C. Healthcare Alliance, also later went to work for Mr. Thompson at D.C. Chartered.

Karen Dale, a spokeswoman for D.C. Chartered, said Tuesday that Mr. Christian and Mr. Smith “have both added significant value to the operations of Chartered and the members we serve.”

In the wake of the federal raid, Mr. Thompson has left both the accounting firm and the health plan, and D.C. Chartered is seeking buyers.