For two decades, Mark Wiener has been the man Portland politicians turn to when they're in a jam. As the city's top political consultant, he helped Vera Katz, Randy Leonard, Sam Adams and many others get elected, then advised them when they faced trouble in office.

"Mark Wiener is the premier political consultant for City Hall candidates," says Jim Moore, a political science professor at Pacific University in Forest Grove. "Working with Wiener is the way to get elected to City Hall."

But new information continues to surface about Wiener leveraging his connections to lobby some of those same people on behalf of Uber. 

WW previously reported Wiener was hired last December as a lobbyist for the ride-hailing company trying to change Portland's taxi rules.

By playing two roles—political consultant and lobbyist—Wiener wielded extraordinary clout, since he was urging rule changes to officials whom he helped get elected and was seeking to re-elect.

Mayor Charlie Hales and Commissioner Steve Novick—both Wiener clients—reversed their opposition to Uber after Wiener began representing the company. Wiener has said he did nothing wrong, because he wasn't being paid by Hales and Uber at the same time.

But newly released emails show that while Wiener lobbied for Uber, he was communicating with Hales about the mayor's political interests.

The emails show Wiener moving between representing Uber and strategizing with Hales. That dual representation raises questions about whose interests Hales and Novick's reversal on Uber served.

Observers say when political consultants lobby their clients, the public loses.

"It looks bad when someone is serving two masters and that leads to a change in policy," says Ben Gaskins, who teaches political science at Lewis & Clark College. "It's impossible to know why they changed their minds, but it could give the appearance of being inappropriate."

Professor James Thurber, director of the Center for Congressional and Presidential Studies at American University, has written about political consultants who also lobby their own clients.

"It's not illegal, but it's unethical," Thurber says. "There's an inherent conflict of interest, it's usually not transparent, and it can really distort the candidate's position if it results in pushing a special interest over the public's interest."

Hales says there's no conflict.

"Mark Wiener has never lobbied me on this or any issue," Hales says. "And while I have not hired him to help me on my re-election campaign, he, like many others, gives me advice, of which I'm free to take or not. He has not been compensated by me or my campaign committee since I have been mayor."

Wiener also makes a distinction between advising Hales and getting paid by Hales.

"At no time during my engagement with Uber have I been paid by or in a contract with Mayor Hales," Wiener says.

Wiener undertook his representation of Uber at a crucial time for the California-based company—and for Hales.

Uber was facing a hostile reception in Portland last December. Portland was the only major city on the West Coast where Uber wasn't operating.

Hales was preparing for a re-election bid, and he needed to shore up flagging support.

On Nov. 25, 2014, Hales wrote to Wiener, who was on a cruise, under the subject line "ahoy!"

"I want to get onto your dance card in two ways upon your return," Hales wrote. "Once for the two of us to meet, and the other for that strategy session that I have tentatively set for the evening of December 29th."

Wiener wrote back about 90 minutes later. "Let me know when you want to do the 2 of us—12/29 is fine," he said.

Hales, who lives near Wiener in Eastmoreland, responded with a breakfast invitation for Dec. 10.

On Dec. 5, Uber crashed into Portland, launching its service illegally.

Eight days later, as WW has previously reported, Wiener hosted a peace gathering in his dining room between Uber managers, Hales and Novick. The two sides agreed that Portland would review its taxi rules if Uber backed out of the city temporarily.

On Dec. 17, emails between Wiener, an Uber policy adviser and one of Hales' top staffers show the trio preparing to make a formal announcement of the deal. Josh Alpert, a Hales aide, wrote to Wiener and Caitlin O'Neill of Uber that day about a draft news release.

"Mark and I talked a few minutes ago about media, etc., so I think we'll all be on the same page once we figure out timing," Alpert wrote.

Wiener chimed in 18 minutes later. "This looks good to me," he wrote. "I'll leave it to you two to solidify the tick tock of the media strategy; what Josh outlined to me on the phone seemed right."

Two days later, Wiener signed a contract with Uber. He has declined to say how much he's being paid for what he calls "strategic advice."

Alpert continued to email Wiener about Uber, sending him a list Jan. 5 of Portlanders who'd been appointed to serve on the mayor's task force on taxi rules, and a draft agenda Jan. 9 for the task force's first meeting.

Then, Wiener turned to Hales' re-election bid.

On Feb. 25, Wiener responded to an email message from Hales' pollster in Oakland, copying the mayor, his then-chief of staff Gail Shibley and Alpert. "Adding Team Hales," he wrote. "We should think about how to distinguish the difference to voters between issues that are 'important' and mission critical."

In April, Hales, Novick and City Commissioner Dan Saltzman, also a Wiener client, voted to legalize Uber and its competitor Lyft, over the objections of local cab companies.

Broadway Cab president Raye Miles says Wiener's close relationship to both Hales and Uber helped give the company what it wanted.

“The whole landscape changed over the course of a weekend last December,” Miles says. “It just went 180 degrees. [Wiener’s] ability to sway at least some city commissioners is obvious.”