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David Wilmot and Jeff Thompson have long been two of the most influential men in District politics. Wilmot is one of the top-paid lobbyists in town, able to command monthly retainers of up to $10,000 from blue-chip clients like Walmart, AT&T, United Healthcare, and the pharmaceutical industry. He’s a near-constant presence at the Wilson Building and can be seen hanging out in the back of mayoral press conferences or testifying before lawmakers for whom he’s helped raise money.

Until recently, Thompson’s empire used to include one of the biggest minority-owned accounting firms in the country as well as a Medicaid managed-care organization that had a city contract worth $350 million a year. Associates say he likes being called “governor,” a nod to his outsized political power. Thompson used to be the go-to guy for pols in need of campaign cash, but his behind-the-scenes star power crashed to earth last year when the FBI raided his home and office and a close associate pleaded guilty to felony campaign finance fraud.

Now, new records obtained by Washington City Paper offer a glimpse at a highly unusual financial relationship between these two power brokers.

Documents stemming from a 2006 lawsuit show Thompson routed funds through Wilmot’s bank accounts to current and former city officials for unspecified consulting work. Although the records include a handful of copies of checks dated 2005 and 2006, the practice may have gone on for decades, according to testimony from the case. “I’ve known Jeff for 40 years,” Wilmot said in a deposition, “and these directives have gone on for as long as I’ve known Jeff.”

Court and campaign finance records also suggest Thompson may have influenced political donations made by entities he paid through Wilmot. Two companies made donations to a Thompson-backed candidate within weeks of receiving payments via Wilmot’s bank account.

What’s more, one of the officials whom Thompson paid—former Ward 8 Councilmember Sandy Allen, who was serving on the D.C. Taxicab Commission in 2006—did not publicly disclose those payments as city law requires, city records show. But Allen says she never worked for Thompson or Wilmot and doesn’t remember being paid by them, though court records include $33,200 worth of checks made out to Allen that appear to be endorsed by her.

The lawsuit containing these records involves a hostile takeover of Independence Federal Savings Bank that Wilmot, who was on the bank’s board of directors, tried to stop. That effort didn’t go well, with Wilmot failing to prevent businessman Morton Bender from controlling the bank and a federal judge mocking Wilmot by calling him part of “the most incurious group of persons in the world,” saying his testimony was “not to be credited,” and finding that Wilmot had violated securities law.

On top of that, Wilmot was ordered to repay the bank nearly $100,000 in legal fees. Because Thompson purchased several bank shares, and sought to buy more prior to Bender’s takeover, details of Thompson and Wilmot’s financial relationship became part of the case’s record.

In depositions, Wilmot testified that Thompson had used bank accounts belonging to David W. Wilmot and Associates, which held Wilmot’s own money and were completely separate from a trust account belonging to Wilmot’s law firm, to make payments to various individuals.

The payments were purportedly for business consulting, according to the testimony given in depositions. But why Thompson, who controlled the checkbook of several companies he owned, didn’t pay these individuals or their companies directly is never explained in the depositions. Neither Thompson nor Wilmot returned requests for comment.

In their depositions, Wilmot and his assistant said Thompson made payments through Wilmot’s accounts to numerous individuals, usually without first getting Wilmot’s permission. “It’s Jeff’s money,” Wilmot said.

The peculiar arrangement caused problems for both men. One time, Thompson began “spazzing” when Wilmot wasn’t around to sign off on a check Thompson wanted, Wilmot’s assistant testified. And Wilmot says he was “very, very upset and very disappointed” after learning that Thompson had drawn a $163,000 check in Wilmot’s name without his knowledge.

The nature of their relationship is further muddied by inconsistent testimony. For instance, both Thompson and Wilmot’s assistant testified in depositions that Wilmot is Thompson’s lawyer. But Wilmot said in the 2006 deposition that he hadn’t been Thompson’s lawyer for several years because he had a conflict of interest. Wilmot has long been a lobbyist for the D.C. Association of Health Plans, an industry group to which Thompson’s healthcare companies belong.

Neither Wilmot nor Thompson discuss in detail in their depositions why Thompson made payments to Allen, the former councilmember who helmed the Council’s health committee that had oversight of Thompson’s health care companies until she left office in January 2005. Court records include copies of four checks of $8,300 each made out to Allen from an account belonging to Wilmot dating from December 2005 to April 2006. Wilmot and his associate testified that those payments were made with Thompson’s money on his behalf. The memos on some of the checks say “consultant fee.”

But Allen says she has no memory of ever doing consulting work for Thompson or Wilmot.

“I can’t see any reason why anybody would write me a check for $8,300,” says Allen, who recently managed Ward 8 Councilmember Marion Barry’s 2012 re-election campaign. The checks are signed “Sandra C. Allen” on the back, but Allen says that while it looks like her signature, someone could have forged it.

Allen joined the D.C. Taxicab Commission in 2006 and was required to file a financial disclosure form indicating any payments of more than $1,000 she’d received from any city contractor. Her form did not disclose any payments from Thompson, who has long been one of the city’s biggest individual contractors.

Court records also show that Thompson paid, through Wilmot’s account, two companies with ties to former city officials whose political giving fits the donation pattern of several other Thompson associates.

Thompson’s political giving has been a hot topic in District politics since last summer, when longtime associate Jeanne Clarke Harris pleaded guilty to felony campaign fraud violations. Harris testified that she and an unnamed co-conspirator (who several people familiar with the case say is Thompson) tried to conceal illegal campaign finance activities—including making numerous straw donations and funneling money into a “shadow campaign” to help Gray win the mayoral race in 2010—by pretending the co-conspirator’s companies were paying Harris for consulting work. Thompson has not been charged with any crime.

Court records from the Independence case include a April 6, 2006 check for $8,000 from Wilmot to a company called Integrated Urban Solutions. The company is owned by Dawn Kum, who was married to Dr. Ivan Walks at the time of the payment. Before he left his post as head of the city’s health department in 2002, Walks played a key role in setting up a program to provide healthcare for the poor that increased Chartered Health’s market share. According to a 2002 Washington Business Journal article, Walks said he set up Integrated Urban Solutions as a nonprofit to do charity work as a side-project to a running a consulting firm that bears his name. Walks said he once did consulting work with Thompson’s former accounting firm, but does not remember receiving payment through Wilmot’s firm to Integrated Urban Solutions.

Kum, who runs programs for special-needs students, says via email that she’s done consulting work for numerous individuals, including Thompson, but did not specify if that work was done through Integrated Urban Solutions. She said she did not know why Thompson would have paid Integrated Urban Solutions through Wilmot’s account.

Court records also show a January 27, 2006 check for $15,000 and a March 6, 2006 check for $5,250 to Emerge D.C., a consulting firm owned by Kelvin Robinson. A former chief of staff to Mayor Tony Williams, who was a close ally of Thompson, Robinson resigned in 2004 after the U.S. Office of Special Counsel investigated allegations Robinson had improperly asked his subordinates to work or volunteer on Williams’ re-election campaign.

Integrated Urban Solutions and Emerge D.C. not only received money from Thompson via Wilmot’s bank account, but also gave money to a Thompson-backed candidate around the time they received their checks.

On March 9, 2006, three days after the $5,250 check for Emerge D.C. was cut from Wilmot’s account, Robinson’s company gave $2,000 to former D.C. Council Chair Linda Cropp’s mayoral campaign, campaign records show. Also, Integrated Urban Solutions and Kum gave $2,000 checks on March 9, campaign records show. Walks gave a $1,000 check on the same day, records show. On April 6, Wilmot’s account issued the $8,000 check for the company. Kum and Walks say Thompson has never given them money to donate to campaigns. Asked whether Thompson had ever solicited a donation from her, Kum replied that she’s “made political donations at many fundraisers hosted by a variety of individuals across the nation.”

More than a dozen of Thompson’s associates also gave checks to Cropp’s campaign on March 9, including his longtime hairdresser, Ian Thorne, and his Los Angeles–based personal assistant, Proteus Spann. One business associate of Thompson who also wrote a check for Cropp on March 9, who asked not to be named discussing matters that could be related to the ongoing criminal investigation, said Thompson asked him to bring several donations to a fundraiser and hand them personally to Thompson.

While the court records are silent as to whether the payments from Thompson to Emerge D.C. and Integrated Urban Solutions continued past 2006, campaign finance records show a consistent link between donations made by those companies and donations made to the same candidates, at the same time, in the same amounts by several Thompson associates through 2011.

As for Wilmot, he’s also played a role in Thompson’s more recent political giving. According to a campaign aide in a council race who was not authorized to speak on the record, at a fundraiser in 2010, Thompson’s assistant delivered several checks to Wilmot, who in turn handed them over to the campaign staffer. Asked to provide copies of the checks, the aide produced several checks from Thompson associates, including three checks from Harris-controlled companies as well as a donation from her personal account.

It turns out the city’s top-paid lobbyist wasn’t just writing checks on the governor’s behalf, but helping deliver them as well.

Illustration by Carey Jordan.