Jeff Thompson

The mastermind behind five years of illicit District campaigning headed to the federal courthouse Monday to show his work.

And what a job he’d done—Jeff Thompson detailed how he spent more than two million dollars on off-the-books campaigns and disguised campaign contributions to politicians across the country in attempts to secure lucrative contracts for his companies. In 2010 alone, Thompson admitted to spending $834,400 on phantom efforts to elect District politicians, including $668,800 to put Vince Gray in the mayor’s office.

On Monday, though, Thompson’s streak came to an end when he pleaded guilty to two counts of conspiracy to break election laws. The man whom friends called “the Governor” and Gray called “Uncle Earl” now stood in court mumbling to a judge about his crimes.

Gray says it’s all lies, except for the Uncle Earl part. After three years of investigating, U.S. Attorney Ron Machen has finally caught the man behind it all, but he promises that this is just “the tip of the iceberg.” Here’s what might lie beneath.

Do They Have It on Paper?

Machen has flipped Gray advisor Vernon Hawkins, Thompson crony Jeanne Clarke Harris, and now Thompson himself. Between the three of them, if Gray did anything wrong, they can tell a jury about it. But what jury would believe people so accomplished at lying that they duped a whole city?

Rather than relying on Thompson’s credibility and his obvious interest in the cushy six-month sentence he’s been promised for crimes that could otherwise earn him five years in prison, Machen might try to use documents to prove that Gray knew about the illicit campaign.

Thompson’s statement of offense offers one possible clue where Machen could head. The document describes Gray delivering a one-page, $425,000 shadow-campaign budget to Thompson in an August 2010 meeting at Harris’ apartment. After already putting up more than $100,000 for Gray’s run, Thompson had demanded the meeting with Gray before he paid more. Maybe that meeting will be what secures Thompson his short jail term.

Machen declined to comment Monday on whether investigators have the budget. If Machen doesn’t have that piece of paper, though, he has more waiting for him. After the feds raided Thompson’s house and office in March 2012, they came away with 23 million pages worth of electronic and paper files.

Thompson hired top attorney Brendan V. Sullivan (who didn’t respond to LL’s requests for comment) and tied up the document review with legal challenges. Last October, Sullivan even asked the Supreme Court to protect his client’s records.

As part of the plea deal, Thompson has to drop his attempts to keep those records secret. The U.S. Attorney’s Office should buy some new filing cabinets.

How Fast Will Machen Move?

By putting so much detail in Thompson’s statement of offense, Machen isn’t leaving Gray or anyone else wondering what he’s looking at. And it’s not just Gray’s alleged campaign misdeeds—Thompson is described in court papers as footing the bill for a driver and luxury SUV to cart Gray around, $40,000 in various benefits for a “close personal friend” of the mayor, $10,000 in cash for a Gray relative to pay off post-primary campaign expenses, and $10,000 to sway what appears to be the Washington Teacher’s Union election on Gray’s behalf.

But will it matter to Gray supporters? Even after years of Gray friends pleading guilty, the mayor still had 28 percent in a pre–Thompson plea poll—and thanks to a large field of candidates, that was enough to lead the race. Will the voters still loyal to Gray through all the earlier disclosures about the shadow campaign really desert him now? When Gray asked the audience at Tuesday’s State of the District address whether they believed him or Thompson, the crowd, shouting “four more years!” didn’t leave any question.

Machen says he doesn’t operate with a timeline, the publicity-friendly timing of the Thompson deal aside. If he doesn’t make his move before the primary, Gray could win—and early voting for the primary starts on Monday.

Is Vincent Orange the Next Target?

Aside from Gray, At-Large Councilmember and mayoral competitor Vincent Orange is the only currently elected official who matches descriptions in court paper of beneficiaries of Thompson’s criminal conspiracy. Once Machen’s done with Gray, is he coming for a slice of Orange?

Orange, who didn’t respond to LL’s requests for comment but told the Post he didn’t know what Thompson was up to, has looked like one of Uncle Earl’s favorite nephews since 2012, when money orders from Thompson network members to Orange’s 2011 at-large bid were discovered to be obviously fraudulent. Hawkins’ position as a semi-official advisor to Orange’s 2011 campaign didn’t exactly make it look more legitimate.

If Orange’s 2011 bid looked tainted before, though, Thompson’s plea deal leaves no question. Before meeting with Orange at his accounting firm’s office in March of that year, Thompson swore in court, he purchased the consecutive, clumsily forged money orders.

Then, court papers say, Thompson installed a politician whose description matches that of Orange, but who isn’t named in the statement of offense, in an office so he could call donors. In a scene that’s begging to be set to the Benny Hill music, filings say Thompson sat in another office setting up straw donations to disguise his own help for Orange at the same time.

Thompson’s plea deal says Thompson “understood” that Orange knew about the illicit help that totaled $148,146. If LL was kicking in nearly $150,000 and risking a potential prison term, he’d certainly hope that the guy he was doing it for knew about it, too.

But Thompson suggested otherwise in court Monday, describing Orange and former D.C. Council chairwoman Linda Cropp, who matches the description in papers of the beneficiary of a 2006 mayoral shadow campaign, as the only pols he backed who might not have known about his illegal help.

Orange has always said he’s innocent. Maybe he really is.

Will Any Candidates Drop Out?

With Machen clearly gunning for Gray and Gray showing no sign of stepping down, the District faces at least the possibility of a Democratic primary winner being indicted by the feds after he’s nominated. With early voting starting on Monday, Gray’s many rivals may wonder whether they should drop out to stop that from happening.

The most obvious candidates to step aside look like Ward 6 Councilmember Tommy Wells and Ward 2 Councilmember Jack Evans, who had 12 and 13 percent of the vote, respectively, in a poll conducted prior to the Thompson plea. That could make them spoilers for Ward 4 Councilmember Muriel Bowser’s bid, which has pulled out ahead of her rivals and is almost within the margin of error of Gray. Nearly three out of every four Democrats polled recently wants someone besides Gray to represent the party; could that percentage weigh heavier on Wells and Evans than their own support does?

Probably not. It’s hard to imagine Evans and Wells overcoming their enmity with Bowser and their loyalty to their own backers. Wells has another reason not to quit: As the only elected official in the race who never took Thompson network money, he’s finally been proven right.

Their campaigns aren’t interested in LL’s scenario. Evans spokesman Jermaine House tells LL that Evans won’t be dropping out of the race since he plans to win it, while Wells campaign manager Chebon Marshall doubts his boss’s votes would go to someone with Bowser’s “thin record” or Evans, “the corporate candidate from Wall Street.”

No one seems more concerned about the effects on the city’s reputation of having an alleged crook in the mayoral suite than Evans, who’s spent years polishing the city’s bond rating as head of the Council’s finance committee. In a statement Monday, Evans told Gray to “do what’s in the best interest of the city” if he’s charged. If Gray decides not to take his advice, though, Wells and Evans may have to consider what’s in the city’s best interest themselves.

What Does This Mean for November?

With Thompson’s plea deal just hours old Monday night, independent At-Large Councilmember David Catania decided to make his own mayoral run official. Catania, who launched a mayoral exploratory committee last year, likely watched Thompson’s plea news with more glee than most: His unlikely path to victory was finally becoming clear.

Nothing about the District’s 41-year-old history under Home Rule suggests that Catania will become mayor: He’s white, he’s gay, and he was a Republican until 2004. And the city’s Democrats still make up three quarters of registered voters. But he’s gained enough city-wide support to fend off challengers for his seat for 17 years, and he can make a play for East of the river voters for his attempts to save the troubled nearby United Medical Center.

Best of all for Catania, though, Gray has a good chance of winning the mayoral primary if he can hold back his Democratic rivals. If only Gray could find another uncle.

Photo by Darrow Montgomery