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For years, District Medicaid contractor Jeff Thompson held his wallet open to connected Washingtonians. As the ongoing federal investigation into Thompson’s illicit funding of Vince Gray’s 2010 mayoral campaign shows, he didn’t care if the law got in the way.

But there’s one problem with taking money from the man who was once one of the biggest crooks in local District politics: When Thompson is hard up for cash himself, he’s going to come back and collect.

That’s what Omar Karim, who once starred in a Wilson Building scandal of his own as a politically wired frat brother of ex-Mayor Adrian Fenty, found out last week. One of Thompson’s companies sued Karim’s company, revealing a mysterious loan that Thompson made to Karim and his firm just a week before the 2010 Democratic mayoral primary that Fenty lost to Gray.

Karim isn’t talking about the mystery loan. Neither is Thompson’s attorney, who filed a motion last Friday to drop the case four days after the complaint was filed. Still, the lawsuit shows again how well connected Thompson was with District officials and the people who orbit around them.

Even before taking a loan from Thompson, Karim was no stranger to the concept of powerful friends. When Fenty occupied the mayoral suite, Karim flaunted his ties to the mayor by referring to him in conversations as “God.”

Those connections led to Karim and his company, Banneker Ventures, playing starring roles in the Fenty administration’s contracting scandal. According to an 18-month D.C. Council investigation released in 2011, Banneker steered some of the $87 million in park contracts it controlled to firms with ties to Karim, including a company owned by fellow Fenty frat brother Sinclair Skinner.

Some of the firms that received city contracts had paid consulting fees to another Karim-owned company, a bit of shadiness that helped convince the Council’s investigator to refer the investigation to then-U.S. Attorney Ron Machen.

Thompson and Karim weren’t strangers at the time of the 2010 primary. In 2013, the Washington Post reported that Thompson hired Karim and Skinner in 2008 to do “community relations work” on his behalf.

In 2010, Thompson and Karim did business again. Thompson’s D.C. Healthcare Systems Inc. holding company, which controlled Thompson’s lucrative Chartered Health Plan Inc. Medicaid contractor, lent Karim’s Banneker a combined $75,000 in equal installments on July 8, Aug. 8, and Sept. 8 of 2010. The loans were backed by promissory notes guaranteed personally by Karim at a rate of 7.5 percent.

Unfortunately for DCHSI and Thompson, Karim and Banneker don’t seem to have been in a rush to pay back the money. Banneker made some payments in January 2012, according to court records, two months before FBI agents raided Thompson’s house and office while investigating the “shadow campaign” he funded for Gray.

Since those raids, Thompson and DCHSI have found a lot of need for a spare $75,000. Thompson, who pleaded guilty in March 2014 to his role in Gray’s shadow campaign, hired Brendan Sullivan, one of the top defense attorneys in the country. Meanwhile, DCHSI has been sued by Chartered—now under District control—for money Thompson supposedly helped pilfer from the Medicaid contractor. For his cooperation with prosecutors, Thompson has secured a plea deal that could result in a sentence as light as six months under house arrest.

A cash-strapped Thompson has had to start selling off his assets, including an office building close to the White House.

To put it bluntly: If Thompson is coughing up money, Karim has to do the same. Thompson’s lawsuit last week wanted $91,266 from Karim, a figure that included $8,558 in late payment fees and $9,708 in accrued interest.

There’s nothing in court records that suggests the loan was intended to be used illegally. While Thompson was a prolific straw donor to District pols, there’s no evidence that this money was used that way. It certainly didn’t go to contributions from Fenty superfan Karim or his company, which both maxed out to Fenty’s re-election campaign nearly two years before the loan were made.

Thompson’s guilty plea, meanwhile, mentions several corrupted elections’ worth of schemes, but doesn’t include any reference to loans related to the 2010 election.

Thompson also had every reason to hope voters would show Fenty the door in 2010. Peter Nickles, Fenty’s attorney general, sued Chartered in 2008, a move that helped convince Thompson to surreptitiously back Gray’s mayoral ambition.

With neither Thompson or Karim apparently willing to reveal more about their financial arrangement, the loan may be most interesting for how it reveals Thompson’s use of DCHSI as a political piggy bank. District watchers will remember that much, if not all, of DCHSI’s money came from Chartered, which was supposed to use its Medicaid contract, worth hundreds of millions in taxpayer money, to help low-income Washingtonians.

Instead, according to a lawsuit filed on Chartered’s behalf in 2013, DCHSI and Thompson looted Chartered through bogus contracts to other Thompson subsidiaries and a line of credit for DCHSI that used Chartered as collateral. That lawsuit suggests there’s a good chance the money Thompson was using to make loans to politically juiced people like Karim originally came from the District’s treasury. (Thompson countersued the District earlier this year for allegedly scheming to take Chartered away from him.)

Karim isn’t the only recipient of DCHSI money to get his or her number called up by Thompson. In January, LL wrote about Dawn Kum, a school operator and the former wife of a District Department of Health official who helped Chartered score its Medicaid contract. Kum’s school received more than $1 million from DCHSI. In December, DCHSI sued Kum and her school last December in an attempt to recover the money.

Kum claims Thompson’s money was meant as a gift; he says it was an investment that can be withdrawn. Either way, both Karim and Kum are learning that Thompson’s generosity doesn’t last forever.

File photo by Darrow Montgomery