In June 2011, lobbyist John Ray found himself on the wrong side of the D.C. Council dais. Once a councilmember himself, he was back as one of the Wilson Building’s top lobbyists, testifying against a bill by Ward 3 Councilmember Mary Cheh that would wrest away his client Joe Mamo’s tight grip on many of the District’s gas stations.

Ray had even brought a letter from the Rev. Jesse Jackson supporting his position, but Cheh suspected the civil rights icon didn’t know as much about the intricacies of gasoline wholesaling as his letter suggested.

“You, Mr. Mamo or Mr. Ray, ginned up this letter,” Cheh said.

Councilmember Phil Mendelson, also at the committee hearing, seemed just as eager to pass the bill that spelled doom—or at least a less lucrative business—for Ray’s client. Still, Ray had one councilmember in the room that he could work with: Vincent Orange.

Orange wasn’t alone in opposing Cheh’s bill. The Washington Post editorial board and Congressional Black Caucus were also against it. But he was the only member of the Council to get an email from Ray associate Tina Ang that day telling him what to say.

Ray, Ang wrote to Orange, wanted to be asked about the letter from Jackson. When Orange got his turn to question the witnesses, he did what he was told. “Can you speak to this letter, please, for the record?” Orange asked Ray.

The question let Ray cast Mamo as a civil rights crusader triumphing in the white-dominated gas business. It also left other councilmembers insisting to Mamo, who would later be sued by D.C. for anti-competitive practices, that the bill wasn’t aimed at him.

Mendelson would call Orange’s loyalty to Mamo “an embarrassment.” But Mamo, Ray, and Orange won eight months later, when Cheh’s bill died on a 6-6 vote.

Ray’s relationship with Orange is nothing new. The Post’s Colby King wondered in 2006, following the disclosure of $15,000 in campaign contributions from Ray and his wife to Orange, how much “Orange’s open door to Ray is heavily greased with greenbacks.” New emails obtained by LL through Freedom of Information Act requests show just how open that door is, with Orange asking for Ray’s advice on dealing with a scandal in the wake of an FBI raid on alleged Mayor Vince Gray shadow-campaign financier Jeff Thompson and Ang asking Orange to “lean on” colleagues about the Mamo bill.

Ray, who served on the Council from 1979 to 1996, is now one of D.C.’s most active local lobbyists. In 2013, Ray’s firm Manatt Phelps & Phillips lobbied for eight clients, including Mamo and Bazilio Cobb, the accounting firm once co-owned by Thompson.

In return for paying Ray, clients get an inside look at Wilson Building string-pulling. Ray and Ang regularly asked Orange to persuade his fellow councilmembers on bills for Manatt clients. Looking for a tax break for a 14th Street NW apartment building, Ang emailed Orange and then-Councilmember Harry Thomas Jr., asking them to try to win over colleagues Kwame Brown or Yvette Alexander. In an email about Cheh’s Mamo bill, Ang asked Orange to “please help us lean on other [councilmembers] too.”

Orange declined multiple requests for comment about individual emails, saying only that his relationship with Ray dates to before Orange entered politics. Ray and Ang kept quiet, too, except for a one-sentence statement saying they would talk if LL requests their emails with the entire Council. (LL’s documents do cover the whole Council for 2011, but only Orange for later years.)

Keeping Orange working means anticipating his flights of fancy. Ray’s staff requested an early copy of Orange’s November proposal for a study to develop the area around RFK Stadium into a sprawling PGA golf course/100,000-seat domed stadium/waterpark/movie soundstage. (What, no casino?) The firm took more direct action in 2012, after Orange endorsed the idea of a Michael Bloomberg–style ban on large sodas at an at-large debate.

Ang forwarded Orange an article about the soda ban and asked him to back off. “Happy Friday, VO!” Ang wrote. “Can you *please* not get too far out there on this one? Council must have more important issues to focus on than soft drinks.” Orange hasn’t made a public statement on a large soda ban since.

Despite his firm’s attempts to rein in Orange, Ray turns out to be the Forrest Gump of Orange’s more recent misadventures, making at least a cameo role in several of them.

Ray represented Sang Oh Choi, the Union Market–area developer and Orange campaign donor whose wholesale grocery store Orange protected, briefly, from a shutdown order by city health inspectors after they discovered rat feces close to vegetables. The incident earned Orange a settlement with the District’s ethics board, but Orange insisted last week that he would do it all again in an attempt to save jobs.

Ray was also copied on emails between Orange and Marc Meisel, the CEO of Rockville-based WorldWide Parking. Orange earned some notoriety from his efforts on the company’s behalf in December, when he threw all he could into preventing the Council from approving a contract for WorldWide rival Xerox. WorldWide had also bundled $20,000 to Orange’s mayoral campaign, a perhaps not-so-coincidental coincidence that Cheh lamented as the “mischief” that comes with the Council approving contracts. Ang says Meisel and his firm aren’t clients.

Ray counsels Orange on how to deal with scandals, too. After the FBI raided Thompson’s home and office in March 2012, reporters—and Orange—started to notice that people connected to Thompson had also contributed $26,000 in money orders and cashier’s checks to Orange’s own 2011 at-large campaign. Orange, an accountant, claimed to have missed the fact that many of the money orders were sequential and signed in the same handwriting.

The District’s Office of Campaign Finance seemed only mildly interested in the issue, with OCF’s report on the case saying they asked Orange if he thought anything shady was afoot, then dropped it when he said he didn’t. Despite that lukewarm endorsement, Orange yearned to proclaim his innocence. He sent Ray a copy of his draft press release on the OCF ruling that the lobbyist found too jubilant.

“Well, you know how I feel about what I think is a premature press release, unless you are willing to address the money order issue,” Ray wrote to Orange. “Regarding VO, this is the issue that is on the mind of the [sic]. Did he knowingly and willingly accept thousands of illegal contributions?”

Ray especially didn’t like Orange describing himself as “elated” after hearing that OCF cleared him: “This should be the mentality of someone who have always insisted his innocence.”

Orange didn’t take Ray’s suggestions and sent out the release without his revisions. The line about being “elated” stayed. Influence, apparently, only goes so far.

Photo by Darrow Montgomery