Federal agents raided the home and office of Jeffrey Thompson, among the largest contributors to D.C. political campaigns, on Friday, prompting Wilson Building observers to murmur excitedly throughout the weekend. But Thompson keeps a pretty low profile, for a guy whose companies and employees have given hundreds of thousands of dollars to politicians.

So LL wrote up a little guide to the perplexed on why the raid shocked insiders so much.

Q: Just how big a deal is this raid?

A: In the world of District politics, it is a very, very big deal. Thompson has poured a ton of money into local campaigns and— surprise!—has won District contracts worth huge amounts.

Q: Who is this Thompson guy?

A: He’s an accountant, a proud UDC alum (go Firebirds!), a big philanthropist, and a major player in District politics since Anthony Williams was mayor.

Q: If he’s so important, why don’t you have a picture of him?

A: He’s media shy.

Q: Tell me more about Thompson’s business activities!

A: Thompson’s accounting firm, Thompson, Cobb, Bazilio and Associates, is one of the largest minority-owned firms in the country. According to Uncle Sam’s count, the firm has won 136 federal contracts worth more than $16 million since 2001. TCBA also regularly does business with the District as well.

But the real money maker for Thompson is his healthcare companies. His Medicaid managed care organization, D.C. Chartered Health Plan Inc., has one of the District’s biggest single contracts, worth more than $300 million a year. LL’s unaware of any other city contract that surpasses that amount.

Q: That’s a lot of money. The District must be paying close attention to the type of work his firms do, right?

A:Well, maybe not. Last summer, LL unearthed a 2005 audit showing that Thompson-owned health care companies were overcharging other Thompson-owned health care companies, with the District picking up the extra costs. The audit led a to a lawsuit, which Thompson paid $12 million to settle (like most settlements, there was no admission of guilt). The little-noted brouhaha did little to crimp Thompson’s earning potential, as his companies have continued to win lucrative city contracts.

Q: What might account for the lack of scrutiny of Thompson’s organizations?

A: If you spend several hours putting together a spreadsheet of how much Thompson, his companies, his employees, his employees’ families, his contractors, his contractors’ employees, his contractor’s employees’ families, and some old friends have given, you can find at least $730,000 in campaign contributions to local campaigns in the last decade that have a link to Thompson. That puts Thompson up there as one of the biggest money men, if not the biggest, in local campaigns. (Also, keep in mind that LL did not include several other donors whose contributions matched the rest perfectly in terms of the amounts, dates, and candidates given to. LL could not find a clear link between those donors and Thompson, so he kept their donations out of the final count.)

Last year, the Thompson network gave almost $80,000 to Maryland Gov. Martin O’ Malley‘s re-election campaign in a single day, campaign records show. Thompson’s also a regular donor to Democrats and Republicans in federal races.

Q: Why are the feds all up in Thompson’s business?

A: LL’s not 100 percent sure why Thompson’s home and offices were raided. If you forced the Wilson Building wags to speculate, they’d probably guess the raid was connected to the ongoing federal investigation of Mayor Vince Gray‘s 2010 campaign, of which the Thompson network gave at least $73,000 by LL’s count.

Another possible connection between Thompson and Gray: Howard Brooks, the mystery Gray campaign aide accused of giving former minor mayoral candidate Sulaimon Brown cash-filled envelopes, may have Thompson ties. One of Brooks’ companies, Techmar, once did transportation work for Chartered, according to Brooks’ resume. It’s unclear if Thompson owned the company at that time.** Brown, whose spectacular flameout got this whole party started, used to work for Thompson’s accounting firm.*

Q: Who else might be sweating the raid?

The Thompson raid has already provided fodder in the at-large D.C. Council race. Challengers Sekou Biddle and Peter Shapiro have both started attacking Councilmember Vincent Orange over the fact that the Thompson network has contributed at least $100,000 to Orange’s political campaigns. More than $40,000 was given to Orange’s at-large bid last year alone.

“Councilmember Orange has a lot to answer for before he can ask the public to return him to office,” says Shapiro in a statement.

LL ran into Orange on Saturday as Democrats were elected their delegates and tried to ask him about Thompson’s past donations. Orange didn’t have much to say except to note that he hasn’t received any money from Thompson for his current campaign (neither has anyone else).

When LL pressed Orange on specific donations from the Thompson network, Orange fired off a series of “no comments” and scampering away like a frightened squirrel. (Ward 8 Councilmember Marion Barry, who observed the exchange, laughed and said “Keep trying, Alan.”)

Orange’s campaign last year accepted several thousands of dollars from the Thompson network in the form of $1,000 money orders. Even corporate donations from Thompson-owned companies gave money orders. Why do we care? Well, The Washington Post has previously raised questions about how Gray’s campaign had an “unusual practice of accepting cash donations and turning the cash into money orders.” Several donors with ties to Thompson are listed in Gray’s campaign finance reports as having given large money orders, the Post noted.

Q: Are other people sweating?

A: Yes, lots, but LL will get to that later.

*This post has been updated.

** An earlier post said Brooks contracted with Thompson. As the updated post notes, it’s unclear if that’s true.

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