On Dec. 13, 2014, Mark Wiener hosted a Saturday détente at his Eastmoreland home between Mayor Charlie Hales and Uber, the ride-hailing company that had entered Portland's taxi market in defiance of City Hall.  

Six days later, Wiener—a paid campaign consultant to a majority of the City Council, including Hales—signed a lobbying contract with Uber.  

Wiener's dual role as consultant and lobbyist, reported last week by WW, played a key role in winning Uber a much-coveted market in Portland. Now it's raising questions about the ease with which campaign consultants can trade on their access to elected officials.  

“There is an appearance of a conflict of interest,” says City Commissioner Nick Fish, “when someone who is representing a company like Uber also represents the person they’re trying to influence.” 

Fish, who doesn’t employ Wiener and who voted against the April deal to allow Uber and its competitor Lyft to operate in Portland, says it’s unethical to allow campaign consultants to lobby city officials they helped elect. “I think the average person would say there’s something wrong with that.” 

But other city leaders don't see a problem. Hales gave Wiener his blessing to accept Uber's money, both men have said. 

Wiener, whose list of Democratic clients reads like a who's who of Oregon politics, is still working for Uber. He told WW last week there was no conflict because he wasn't being paid simultaneously by Uber and the Portland elected officials he represents.  

“I am neither under contract nor being paid,” he said, “by anyone at City Hall.”  

He declined repeated requests by WW to disclose how much Uber was paying him, claiming the terms of his nondisclosure agreement with the company didn't allow it. Uber's lobbying reports to the city show it has spent at least $62,000 lobbying City Hall during the first six months of 2015—far more than any other group has reported.

Wiener's dual role wasn't against city rules. But Uber appears to have broken at least one lobbying rule soon after hiring him.  

It didn't report Wiener had acted as its lobbyist until April 10—almost three months after accurate lobbying statements for 2014 were due. That might be a violation of Portland's 2006 rules on lobbying, designed to bring greater transparency to City Hall.  

On April 21, 11 days after Uber reported Wiener's work as a lobbyist, Hales joined City Commissioners Steve Novick and Dan Saltzman (also Wiener clients) in a contentious 3-2 vote to legalize Uber. 

Portland City Auditor Mary Hull Caballero tells WW she will investigate whether Uber broke the city's 2006 rules; the company has been warned about compliance with those rules, she adds. Portland's enforcement system is triggered only by a complaint to the auditor. 

Uber says it didn't break city rules because Wiener was giving the company "strategic advice" in December, not lobbying for it. Portland, however, defines lobbying broadly to include time spent preparing to communicate with officials.

Wiener hosted the Dec. 13 meeting in his dining room eight days after Uber defied city rules by running cars here (“Drive,” WW, Dec. 31, 2014). Hales, Novick and two Uber managers attended—and agreed the city would reconsider its taxi rules if Uber backed off.   

Portland's elected officials are required to disclose all meetings with lobbyists on their calendars. But Novick's December 2014 calendar makes no mention of the Dec. 13 meeting. The mayor's calendar does not include the Dec. 13 meeting. 

Last week, after WW reported Wiener's dual role in Uber's arrival, Hales told KATU-TV there was nothing wrong with Wiener's work for Uber and that he approved it.  

WW asked Wiener why he sought the mayor’s permission. “I checked with Mayor Hales to ensure that my involvement would be potentially helpful and productive in forwarding good public policy,” Wiener said, “as Uber and the city tried to repair a relationship that had become very difficult.” 

In 2010, Wiener told The Portland Mercury that he didn't try to influence public policy. "I made a decision a long time ago that I would not be a lobbyist, and I'm not," he said. "I help people get elected."

Today, he says, "I don't really think of what I do in this regard as lobbying as it is classically defined."

Debbie Aiona, a director with the League of Women Voters of Portland, says the public should be concerned about the issue.

"The issues these people are working on are important to all of us," she says. "We want people working on them who don't have conflicts of interest."

Fish wants Portland to follow the lead of lawmakers in New York state who've also confronted the issue of campaign consultants acting as lobbyists. There, lawmakers have attempted to require consultants to report their activities under regulations similar to those for lobbyists.

Short of that, Fish thinks elected officials should make individual pledges not to let their own political consultant lobby them.

“That’s how you solve the problem,” he says. “It’s too much of a gray area, and at some level it just doesn’t look good.” 

Correction: The original version of this story incorrectly said Portland imposed lobbying regulations in 2007. It was 2006. We regret the error.