Jeff Thompson pulled it off, until he didn’t.

The man who was once one of the biggest financiers in District politics laid it all out in court today while he pleaded guilty to two conspiracy charges: the $278,000 he spent trying to elect Linda Cropp mayor in 2006, the $668,000 he spent backing Vince Gray four years later, the tens of thousands in favors he says he did for the mayor, the hundreds of thousands more in other illicit campaigns and straw donations, and the tax fraud to cover up those straw donations. And that’s not even everything.

“What you learned about today is only the tip of the iceberg,” U.S. Attorney Ron Machen said this afternoon after Thompson’s plea hearing.

It’s a hell of a tip. Thompson, the former owner of a well-connected Medicaid contractor and part owner in an accounting firm, pleaded guilty today to organizing multiple shadow campaigns and straw donation schemes that Machen said amounted to “a veil of corruption over the District of Columbia.” With the exception of former Councilmember Michael A. Brown, none of the politicians Machen said benefited from Thompson’s illegal actions have been charged with any crimes.

The most immediate impact in the Wilson Building will likely be felt in the mayor’s race, with Thompson’s claims in open court and in filings contradicting Gray’s claims that he didn’t know about the illicit effort to get him into the mayoral suite. While Gray claimed that Thompson’s charges were “lies” in an interview with the Washington Post, Thompson’s statement of offense features Gray arriving for an August 2010 meeting to personally deliver a $425,000 budget for how to spend Thompson’s money on a get-out-the-vote effort.

Prosecutors and Thompson say the meeting at Thompson associate Jeanne Clarke Harris‘ apartment was arranged after Thompson, who had already spent $102,800 through his healthcare holding company and accounting firm, said he would only consider spending more to defeat then-Mayor Adrian Fenty after meeting with Gray personally. Harris proved far more useful for Thompson than just as a host—-two of her companies were described by Machen as a “familiar pass-through” for Thompson’s money. (She entered her own guilty plea in 2012 to charges that she acted as a straw donor for shadow campaign cash and is cooperating with the feds.)

At the end of the meeting, Gray allegedly expressed his “gratitude” for Thompson’s help by calling him “uncle,” a reference to “Uncle Earl,” the alias they had decided to use for Thompson to hide his support for Gray from Fenty. (Thompson told prosecutors he feared supporting Gray publicly would lead to retaliation by Fenty against Thompson’s lucrative contracts.) Gray conceded in his Post interview that he called Thompson “Uncle Earl”—”that part is true,” he told the Post—but he said he was unaware of any illegal activity on his campaign’s behalf. 

Thompson’s largesse for Gray allegedly went beyond the September primary. He claims to have paid $10,000 in cash to a “close family member” of Gray’s to pay for people who worked on the campaign. In November 2010, Harris told Thompson that Gray wanted to him to help sway a run-off union election. The plea doesn’t name the union, but the Washington Teacher’s Union had a run-off that month; the union had backed Gray aggressively against Fenty. Thompson spent $10,000 on the race.

Thompson claims to have provided Gray with less political help. Court papers say he paid $40,000 for “home improvements, employment, and other items” for someone described as a “close personal friend” of the mayor’s sometime after Jan. 2, 2011. And court record say Thompson paid for former D.C. Council candidate Mark Long to drive Gray during the campaign… in a luxury SUV leased by Harris.

Machen insisted at his press conference that there’s no agenda behind the plea, which comes just a week before early voting starts. “I don’t feel that there’s a timeline,” Machen said.

The campaign finance misdeeds Thompson swore today he committed started in 2006, when he funded a $278,000 effort on behalf of then-D.C. Council chairwoman Linda Cropp’s mayoral effort. When then-rival and future Councilmember Michael A. Brown, who makes multiple appearances in Thompson’s statement of offense, looked like he’d steal votes from Cropp, Thompson convinced him to drop out. Brown’s price: $200,000 for himself, and a $150,000 consulting contract from one of Thompson’s companies to Brown’s employer. Cropp, who according to Thompson may not have known about the campaign, went on to lose to Fenty. (Brown pleaded guilty last year to a federal bribery charge, and like Harris and several Gray 2010 campaign veterans, is now working with prosecutors in exchange for leniency in sentencing.)

Thompson funded a shadow campaign on Brown’s behalf the following year, when Brown ran against Fenty protege (and now mayoral candidate) Muriel Bowser for the Ward 4 D.C. Council seat Fenty had vacated. The campaign, which cost Thompson roughly $20,000, didn’t succeed in putting Brown in office.

Still, Thompson remained committed to Brown, funding another $100,000 shadow campaign so Brown could win an at-large seat in 2008. Thompson also spent $100,000 trying, and failing, to get Long elected to an at-large seat. That same year, Thompson spent a whopping $809,000 backing Hillary Clinton‘s presidential campaign, including funding a lawsuit over Democratic primary rules and bankrolling a protest.

Thompson also didn’t just spend on the mayor’s race in 2010. He paid $26,000 for a campaign whose description in court papers matches that of Ward 6 Council candidate Kelvin Robinson, in an unsuccesful attempt to oust would-be mayor Tommy Wells. Thompson also contributed $140,000 to Jeff Smith‘s failed Ward 1 campaign against incumbent Jim Graham, who put out his own statement today about the plea.

Thompson’s plea could also affect the political career of Councilmember Vincent Orange, who (say it again, everybody) is also running for mayor. Court filings say Thompson’s last campaign, which cost him $148,146, went to benefit Orange’s successful at-large bid.

Thompson only decided to back Orange after ordering a poll in January 2011 of the field, then allegedly meeting with Harris and Gray and Orange associate Vernon Hawkins, who has already pleaded guilty to his own role in the Gray shadow campaign. Orange showed well in the poll, so Thompson says he met with him in his accounting firms office on March 10, 2011, a campaign finance filing deadline. Thompson had bought the famously clumsy money orders that went to Orange’s campaign earlier that day.

After meeting with Orange, Thompson allegedly installed him an office in his firm to call donors. Thompson, meanwhile, sat in an another office setting up straw donations. Former Ward 6 candidate Robinson, court papers say, was also at Thompson’s office, and, after taking money orders and other contributions from Thompson, sat with him and filled out Orange’s Office of Campaign Finance report.

The statement of offense says Thompson “understood” that Orange “was aware” of the illicit activity, but Thompson claimed in court that he wasn’t sure whether Orange and Cropp knew about the crimes committed on their behalf.

Machen echoed Thompson, saying that not every candidate knew as much as others. “There are varying degrees of knowledge,” the prosecutor said.

Machen promised that Thompson’s plea marked a new stage in the investigation. As to where it’s headed next, Thompson urged anyone who had made a deal with Thompson to come forward.

“I promise you we are not going away,” Machen said.

Photo by Darrow Montgomery