One name sums up the ethical landmines that come with councilmembers having side jobs: Jack Evans.

Evans, Ward 2’s councilmember, is also the city’s longest serving D.C. Council rep. He has long supplemented his Council salary—totalling more than $130,000 a year—with outside work. Now, new documents obtained by LL through the Freedom of Information Act show the thorny ethical lines Evans has to navigate with his side job.

In his last gig, Evans’ longtime six-figure job at law firm Patton Boggs didn’t create many ethical issues, since the firm didn’t represent lobbying clients in the District.

Evans’ new side job, on the other hand, makes a parody of his claim that he’s only representing his Ward 2 constituents. After leaving Patton Boggs, Evans has now signed on with Manatt, Phelps, & Phillips—the same law firm that is home to top lobbyists who regularly sweat city officials.

Evans’ work at Manatt puts him in meetings with John Ray, the former at-large councilmember who has remade himself into one of the Wilson Building’s most prominent lobbyists.

When LL originally reported the relationship between Evans and Ray back in March, Evans’ office said the relationship was vetted by the Council’s attorneys and the city Board of Ethics and Government Accountability.

Ray carries a lot of influence in the District. His clients include now-merged power heavies Pepco and Exelon, as well as District gas baron Joe Mamo. He’s connected enough elsewhere in the Council that he can pitch At-Large Councilmember Vincent Orange on what questions he wants asked at hearings.

Evans might not even have his new side job were it not for help from Ray, who was long involved with Evans’ consideration at Manatt, according to Evans’ Council calendar.

On July 13, 2015, for example, Evans and Ray had breakfast at the Hay-Adams hotel to “discuss Manatt.” Two days later, they met again, this time with Manatt partner Doug Boggs. In September 2015, Ray and Evans video-conferenced in Manatt’s offices with another partner in the firm.

Ray might not have to report these interactions with Evans on his lobbying disclosure forms, but it’s impossible to imagine that they didn’t affect Evans. LL would certainly feel indebted to a company which amplified his income to the tune of $60,000 a year. (Evans spokesman Tom Lipinsky tells LL that the Council’s attorneys and the ethics board review potential issues with his boss’ side job on a “case by case basis.”)

Evans joined Manatt in October 2015, but his contacts with the company’s clients continued long after that. There were photo shoots and orientation dinners. Evans started attending fundraisers at Manatt’s office—including for people like Attorney General Karl Racine and Ward 4 Councilmember Brandon Todd.

Now Manatt has inextricably connected Ray with Evans. Thanks to the rule that allows councilmembers to work for outside interests—even ones that seek to influence the city—Evans could be up to anything. And even if he’s not, he simply can’t avoid the appearance of it.

With Ray, Evans has met with multiple prominent developers, including convicted real estate fraudster Scott Nordheimer. While it’s impossible to know for sure the machinations in and around Manatt, Evans’ job there potentially offers businessmen access to Evans that his own voters don’t have.

Consider Evans’ Jan. 12 meeting with Ray, where the calendar notice includes “re: tony cheng.” That would be the same restaurateur and major Chinatown muckety-muck Tony Cheng who took a felony charge in 2014 as part of his role in a taxicab scheme.

It doesn’t stop there. Evans’ calendar includes a Jan. 22 meeting with a representative for Deputy Mayor for Planning and Economic Development Brian Kenner to discuss the Dupont Underground art space. Then there’s Evans’ meeting with Ray and gas station mogul Hamood Abutaa “re: inspection stations.”

If there’s anything nefarious there, we might never know. Perhaps it was part of Evans’ side job. Ditto his multiple meetings in March with Ray, who appears to have gained far more access to Evans than he ever had before Evans worked for his firm.

It’s enough to make LL pity Del. Eleanor Holmes Norton. When Evans and Ray walked into her office on April 6, what was she thinking?

Was Evans acting as a councilmember—or as a co-worker of one of the District’s most powerful lobbyist?

Who cares?

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Correction: An earlier version of this story said that a meeting between Evans and a staffer for Brian Kenner took place at Cafe Milano. In fact, it took place in a city office building.