Last summer, Jeffrey Thompson, a politically connected accountant whose Medicaid-managed care firm holds one of the District’s largest contracts, had a short meeting with a councilmember up for re-election.

After some chit-chat, the two talked turkey.

“He said, ‘How much do you need,’ and I came up with a number, and he said he would raise it,” says the councilmember, who asked to remain anonymous while discussing private conversations about political contributions. “Campaign fundraising is messy.”

Not in this case. A week or so later, the money arrived all at once in a bundle of checks, the councilmember said. Each donation was for the maximum $1,000. The donations mostly came from various LLCs owned by Thompson, as well as from some employees of his accounting firm, Thompson, Cobb, Bazilio & Associates Inc.

Judging from campaign records of the last decade, Thompson’s conversation with the councilmember was not a rare occurrence.

A review of campaign records shows that Thompson, his companies, employees at his companies, companies that do business with companies he owns, and others with some sort of link to Thompson have given about $630,000 in direct campaign contributions over the last 10 years. Add in contributions from Thompson and his companies to political action committees and elected officials’ constituent services funds, and the total shoots past $730,000.

That money puts Thompson in a rarified world of the District’s top political donors, with a good chance of being the top individual money man. (Thompson didn’t respond to multiple requests for comment from LL.) Over the time Thompson has been pumping cash into politicians’ campaigns, he’s enjoyed a type of most-favored contractor status with the District. His various companies have lengthy and large city contracts, including a more than $320 million-a-year deal for his Medicaid-managed care provider, DC Chartered Health Plan Inc.

Thompson’s campaign donations are worth a closer look not simply because he makes a lot of money off District taxpayers, but also because no one else seems to be looking. There’s no good-government watchdog group in D.C. keeping close tabs on who is funneling large amounts of money to District pols, in part because it’s not easy. It took a lot of detective work to track the perfectly legal ways Thompson directs money to campaigns, and even more hours of tedious data entry by LL and his interns to compile the Thompson money list.

Before we peer inside the Thompson money network, a quick word on methodology: LL only went back to 2000 because that’s how far back the Office of Campaign Finance’s online records go. LL might not have found all the donors with connections to Thompson, and some donations LL counted may have had nothing to do with him; employees of companies connected to him might have contributed without knowing he was giving, for instance. But LL found more than 50 people or companies that seem tied to Thompson, most following a similar giving pattern: the maximum allowable contribution, to the same candidates, at roughly the same time.

Some links in the Thompson network are direct: Thompson’s personal donations total more than $30,000, and money from his well-known companies, like the accounting firm Thompson, Cobb, Bazilio or Chartered Health, adds up to about $110,000.

But LL also found a handful of LLCs that have no presence on the Internet and no listing in phone books, though they use the same address as Thompson’s accounting firm to make campaign contributions. The LLCs, which include “Bright Star Entertainment” and “JT Real Estate Holdings,” also share a pattern of giving maximum contributions to Thompson-backed candidates at the same time as other Thompson entities send money. LLCs like these gave about $43,000 to various campaigns.

Then there are employees at Thompson’s companies who largely follow the same pattern. All told, LL counted about $226,000 from that group. Moving a bit farther from Thompson are donors who live at the same address as his employees, who give to the same Thompson-backed candidates. They account for about $78,000.

Next up are a handful of contractors who work for Thompson’s companies. For instance, there’s Insuraty, a Bowie, Md.-based employee benefits firm that contracts with Thompson’s accounting firm and Chartered. The company (which Maryland records show currently has its business license forfeited) and its president, Chris Lawson, have given nearly $40,000 to various D.C. politicians.

Insuraty’s director of marketing, Michelle Haywood, and a company she is linked with, DivaGifts Inc., gave an additional $24,000. In all, records show contractors with Thompson’s companies, and those linked to contractors, have given about $94,000.

There are also some links to Thompson that appear to be just coincidental. Carrietta Butts is a customer service specialist in the career services department at Georgia State University in Atlanta, who has given $7,500 to Thompson-backed candidates. Butts tells LL she’s never lived in the D.C. area but regularly visits family here. She says she and two Georgia-based relatives (who have kicked in an additional $8,000 to campaigns in the last two years) rely on their District relatives for guidance in political giving. “We’re very old friends,” Butts says of Thompson, but adds that her donations were in no way influenced by him. When LL calls Butts a second time, she says she’s more of an acquaintance than a friend of Thompson’s.

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As for where all this money goes, the Thompson network is wide as it deep. Thompson or companies or people connected to him has given to every sitting councilmember except Ward 6’s Tommy Wells.

On the high end is At-Large Councilmember Vincent Orange, who has gotten at least $100,000 during the last decade. Records show Thompson’s network is responsible for at least $43,000 of what Orange raised for April’s special election, or about 14 percent of his massive $317,000 haul. Orange did not respond to multiple requests for comment.

Like any political donor, Thompson likes to reward winning. Former Mayor Adrian Fenty’s re-election campaign pulled in more than $50,000 worth of donations from the Thompson network, most of it in early 2009. In June 2010, as it was becoming increasingly clear that Vince Gray stood a chance of winning, the Thompson network sent him more than $25,000. By the end of the election, Gray’s total tally from the Thompson network was about $74,000.

The exception to the rule: Wells, who didn’t get anything after creaming Thompson-backed Kelvin Robinson (who pulled in $500 donations from at least 27 donors in the Thompson network for a total of $13,500).

So has all the money Thompson directs to the District’s politicians paid off? That’s tough to measure, but it does seem like few politicians are eager to take too close a look Thompson’s city contracts. An outside audit of Chartered Health’s books in 2005, ordered by the D.C. Council, led to the District suing Thompson and accusing him of fraud. The case was quietly settled with Chartered agreeing to pay $12 million (with no admission of wrongdoing), according to documents obtained by Washington City Paper, and didn’t seem to an affect on Chartered’s continued business with the District. (Even more recently, The Washington Post reported this week that the District will pay Chartered $10.2 million to settle a different contract dispute.)

In any event, the bigger issue in LL’s mind is how difficult it is to keep track of the Thompson network and others like it. The Office of Campaign Finance has lax requirements about donors reporting who their employers are, and doesn’t make it easy to sort large amounts of campaign data in ways that would show connections between donors.

Wells has proposed legislation aimed at ending the legal practice of bundling, or using multiple LLCs to give to the same candidate. Given the variety of ways Thompson has directed money to campaign coffers, the proposal seems unlikely to have much of an effect on overall campaign giving.

The real focus of campaign-finance reforms needs to be on making contributions more transparent. After all, LL only has so many interns.

With additional reporting by Nick DeSantis and Jess Mahanes.

Graphic by Brooke Hatfield, photos by Darrow Montgomery

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