Mayor Rahm Emanuel's personal email accounts have served as a private avenue of influence where executives and investors sought favorable action from City Hall, raising questions about whether some of the messages crossed the line into lobbying and violated the city's ethics law, the Chicago Tribune has found.

Usually, such requests don't become public. But late last year, pressure from open records lawsuits resulted in Emanuel releasing a trove of emails in which he conducted public business on personal email. The messages offer a rare look at how the mayor operates out of the public spotlight and reveal who has his ear.

Now, a Chicago Board of Ethics that had long been viewed as toothless is reviewing details on potential lobbying activity it didn't have the wherewithal to uncover itself because it lacked investigative power. The Emanuel-appointed panel, which is evaluating the emails, enforces the city's broad lobbying law that covers many types of contact with government officials. The ethics board determines whether individuals have violated the rules, and it handed out a record $90,000 fine last month in the first case to emerge since the emails became public.

Hit with the penalty was former Uber executive David Plouffe for illegally lobbying Emanuel on the city's ride sharing ordinance. Plouffe, who managed former President Barack Obama's 2008 campaign, sent an email to one of the mayor's two personal accounts asking Emanuel to help the company on regulations for picking up travelers at Chicago's two airports. Plouffe and Uber argued the size of the fine was "absurd," but the ethics board stood by its ruling, noting the city's lobbying law called for a $1,000 fine for each business day Plouffe failed to register as a lobbyist, starting five days after he contacted Emanuel.

Woven throughout the 2,696 pages of emails are another possible 26 instances where lobbyists, corporate executives and longtime Emanuel associates and campaign donors sought action from — or access to — the mayor or city officials but did not register as a lobbyist or report their contact to the ethics board, the Tribune has found.

The release of the emails has raised the prospect that the ethics panel will take further action, as the board has announced it sent notices to five more potential violators and indicated it could consider more cases. If the ethics board were to find that the instances the Tribune identified were violations of the law and take the same maximum penalty approach as it did in the Plouffe case, those individuals could be on the hook for as much as $13.9 million in fines.

The reason the potential fines could be so large: the ethics law calls for penalties based on how long a lobbyist takes to register after first contacting City Hall. The law doesn't take into account the nature or frequency of the lobbying, just whether the registration happened. So if someone contacted a city official years ago and didn't register as a lobbyist, the potential fine could exceed $1 million.

Full text of emails to Mayor Rahm Emanuel that raise questions about possible lobbying violations View/search document collection View/search document collectionRead the story

Scattered throughout the mayor's emails are messages that could raise questions about whether ethics infractions occurred. They involve issues ranging from Airbnb pushing back against City Hall home rental regulations and American Airlines executives asking for Emanuel's support in Washington for a corporate merger to United Airlines negotiating on expansions at O'Hare International Airport and Chicago Cubs chairman Tom Ricketts seeking added Wrigleyville security.

None of the individuals involved in those examples registered as lobbyists after contacting Emanuel or his administration on public policy issues. Why did so many individuals use the mayor's personal email accounts to contact him about City Hall decisions?

Emanuel declined to be interviewed, and his spokesman did not directly answer.

"Like every other public official, people routinely ask the mayor questions, give him ideas and provide input all day, every day," Emanuel spokesman Adam Collins said. "Ministers and mentors, business owners big and small, parents and residents across the city do it by email, at events, on the train, at the grocery store and at just about every other place."

The possibility of steep fines for lobbying infractions has served as a wake-up call to a city government cottage industry that long has operated in the shadows. It's left lobbyists and business executives nervously calling the mayor's office worried about the possible ramifications, sources close to the Emanuel administration said.

Some people who sent emails requesting help from the mayor or his aides told the Tribune their actions did not constitute lobbying, so they weren't subject to the city's ethics law. Others said they were unfamiliar with the law or chafed at the very notion that they could be considered as lobbyists, insisting they were only speaking as constituents or on behalf of friends.

Cindi Canary, a longtime government reform advocate who in 2012 headed up a task force established by Emanuel to update city ethics and lobbying laws, said "the best way to get people to comply is for them to realize there are consequences for not complying."

"This is about public information. That is why we ask people to register when they lobby, so we've got a source of what the influences are in making decisions, just like we report campaign contributions," Canary said. "These are things that should be on the record, and when they're not, it's appropriate to issue fines and put everybody else on notice."

Lobbying law

For years, Emanuel and his administration would not release or acknowledge the existence of the mayor's emails in which he conducted government business on his personal accounts, arguing the state's open records laws didn't require them to do so. The Tribune and Better Government Association sued, challenging that notion. In December, the judge in the Tribune case ordered Emanuel to provide an index of emails sought by the newspaper related to public business sent to and from his personal accounts.

Less than two weeks later, Emanuel settled the BGA lawsuit, agreeing to release thousands of emails from his rahmemail.com and gmail.com accounts. The Tribune case is ongoing, but the emails released so far have brought fresh attention to the city's ethics law, a sweeping measure that defines a lobbyist as someone who "undertakes to influence any legislative or administrative action" by city officials, employees and the City Council or its committees.

Mayor Rahm Emanuel Brian Cassella / Chicago Tribune

Mayor Rahm Emanuel greets people before his annual infrastructure address Feb. 9, 2017, in Chicago.

Mayor Rahm Emanuel greets people before his annual infrastructure address Feb. 9, 2017, in Chicago.

(Brian Cassella / Chicago Tribune)

A person does not have to be paid by a company or party to be considered a lobbyist — they just have to try to influence city officials on behalf of another individual or entity. Lobbyists are required to register with the city, take a training course and file reports every three months detailing their activities, including whom they lobbied, for whom they lobbied and any political donations or gifts to city officials. Exempt from registering are individuals acting solely on their own behalf or representing nonprofit groups that don't have for-profit members.

If someone seeks to influence City Hall action and does not register or report their activities, they are subject to fines. Lobbyists who register but fail to report lobbying activity are subject to fines of up to $2,000 for each contact they don't report. Companies that hire lobbyists who fail to register are subject to one-time fines of up to $2,000.

The largest is the $1,000-a-day fine for failing to register within five days of contacting city officials. That's designed to create immediate transparency on which interests are seeking to influence potential government actions as those decisions are being weighed by city officials.

The point isn't to discourage interaction with government, Canary said, but to ensure that interaction is transparent so the public knows the genesis of decisions and whether they were "in the public interest" or "hijacked by lobbyists."

"We want people to talk to their aldermen, all kinds of things like that, but when it is lobbying — when you are actively trying to get the government or a government official to move a piece of legislation or to assist in development or to do something else the city can do — you must register," Canary said. "The public has a right to know who is trying to utilize city resources in that way."

When the ethics board fined Plouffe $90,000 for lobbying Emanuel on the city's ride sharing regulations, he and Uber objected, arguing Plouffe should only be fined $1,000 for his contact with the mayor while not registered and not for each of the 90 business days he failed to report his contact.

"Mr. Plouffe and company argue that this leads to an absurd result by having the board punish those, like him, to the same degree it would punish a person who actually had engaged in lobbying activity every day" for the 90 days, the ethics panel wrote in describing Plouffe's argument for a lower fine.

The ethics board ruled that handing down only a $1,000 fine would encourage unregistered lobbying activity until someone was discovered or caught. "There would be no deterrent effect as to unregistered lobbying at all," wrote William F. Conlon, the board's chairman. "At the core of Chicago's lobbying law ... is the prompt and public disclosure of lobbying activity."

Airbnb legislation

Included in Emanuel's emails are two individuals representing home rental company Airbnb. They contacted Emanuel as the city was crafting new regulations for the company that would dictate which types of owners could rent their homes and how much in city taxes they would pay.

Marc Andreessen, a tech giant who co-founded Netscape and serves on Facebook's board, reached out as early as May 2013, introducing the mayor to Airbnb co-founder and CEO Brian Chesky.

In November 2015, Andreessen requested that the mayor meet with Airbnb officials to "discuss the shifting home sharing regulatory landscape." Emanuel responded, "I will have my staff arrange."

Andreessen's email also included detailed internal memos from Airbnb noting their concerns with Chicago's drafting of new regulations. Among them was a message from Airbnb's global policy head Chris Lehane noting the company was "concerned about the direction things are going. We have been told the regs will contain several items that don't work for home sharing."

A month later, Andreessen emailed Emanuel to note Airbnb "is looking forward to bringing onboard their new senior policy lead from Chicago who we know is a strong supporter of yours." Andreessen asked Emanuel if it would be OK if the new hire started in February. The mayor requested a phone call to "discuss timing."

On Feb. 1, 4th Ward Ald. Will Burns announced his resignation to become Airbnb's director of Midwest policy and senior adviser. Burns announced the start date of his new job would be March 1, as Andreessen had described in another email. Burns did not respond to requests for comment.

Airbnb spokesman Ben Breit said the company hired Burns "for one reason — he is an incredibly talented and well respected community leader."

The City Council eventually passed an ordinance despite critics' complaints that it wasn't tough enough on home rental listing companies. Breit said the legislation "was in no way related to any of our personnel decisions."

Breit acknowledged the company asked Andreessen, an investor and adviser for the company, "for an introduction to the mayor." Airbnb has not been contacted by the ethics board, Breit said.

Andreessen could face a fine of up to $330,000 if city ethics officials were to find him in violation and fined him from the point he contacted the mayor in 2015. He did not respond to requests for comment.

Emanuel also received several messages on behalf of Airbnb from Mark Kelly, a retired astronaut and husband of former U.S. Rep. Gabrielle Giffords. The mayor recruited Giffords to run when he led the Democratic Congressional Campaign Committee.

A couple weeks before the City Council vote in June, Kelly sent Emanuel four messages trying to set up a meeting for Airbnb on the legislation.

"The leadership at AirBnB asked me if I could reach out to you to see if you would meet with them," Kelly wrote on June 6.

"Let me think about it," Emanuel responded.

In Emanuel emails, some lobbyists registered but didn't report contacting mayor Bill Ruthhart and Hal Dardick

Most of the instances that raise questions about potential lobbying violations found in the thousands of pages of Mayor Rahm Emanuel's personal emails center on individuals attempting to influence City Hall and then failing to register as a lobbyist.

In three cases, however, lobbyists who were...

Most of the instances that raise questions about potential lobbying violations found in the thousands of pages of Mayor Rahm Emanuel's personal emails center on individuals attempting to influence City Hall and then failing to register as a lobbyist.

In three cases, however, lobbyists who were...

(Bill Ruthhart and Hal Dardick)

"They are just looking for a chance to discuss their issues with you and state their case," Kelly later wrote.

Breit said Kelly "has no formal or financial relationship with Airbnb." Kelly spokeswoman Pia Carusone said Kelly "was not asked by anyone who works at Airbnb to contact any city official nor did he have a relationship with the company. He simply passed along a friend's request for a meeting."

Carusone acknowledged that Kelly contacted Emanuel at the request of an Airbnb investor, whom she did not identify other than to say it wasn't Andreessen. If the ethics board were to find Kelly in violation of the lobbying law, he could face a fine of up to $187,000 because his contact with Emanuel dates back to the middle of last year.

American Airlines merger

In another case, executives and lobbyists with American Airlines and US Airways urged Emanuel to back a merger, according to a review of the mayor's personal emails, official calendars and other public records. That position would have put the mayor in opposition to an Obama administration effort to kill the deal over concerns it would be unfair to consumers.

Before Emanuel weighed in, there was a flurry of activity from the airlines seeking to leverage Emanuel's influence in Washington and status as Obama's first White House chief of staff. The mayor and the companies' executives met at his City Hall office and a Washington hotel.

As the airline lobbyists were pushing Emanuel to back the merger, the mayor was pushing his own agenda: getting the airlines to back long-stalled plans to modernize and expand O'Hare International Airport, records show.

The airlines first announced the merger in February 2013. Less than two months later, Emanuel's official calendar shows he met at City Hall with veteran federal lobbyist Daniella Landau, who had been hired by American; Doug Parker, then-CEO of US Airways; and another US Airways executive.

By September 2013, Emanuel and his top aides were weighing whether the mayor should sign a letter addressed to the Obama administration, supporting the merger. Landau sent a Sept. 22, 2013, email to then-city attorney Steve Patton to relay a conversation she "had with Rahm last Thursday night when he was in DC," noting the mayor had "expressed his dismay with the Justice decision" to block the airline merger.

Emanuel's calendar shows only one event in Washington the day Landau mentioned — an evening "non-city" event at Nopa Kitchen & Bar. Less than two weeks later, Emanuel reported $52,000 in campaign contributions from Washington donors, including $10,300 from Landau and her lobbying firm, records show.

In her email to Patton, Landau noted that she was drafting the pro-merger letter for the mayor to sign after recent calls Emanuel had about the merger with herself, Parker, then-American Airlines CEO Tom Horton and Will Ris, American's then-in-house lobbyist.

Three days later, Landau sent another email to Emanuel with a copy of the letter to the Justice Department she had written for him to sign, according to emails City Hall first provided to ProPublica through an open records request. In that message, Landau also asked the mayor to "agree to provide 2-3 quick phone interviews with key reporters" to push "the pro-merger message."

At the same time, emails from officials in the city's Aviation Department noted plans for the mayor to meet with the two airline CEOs, Horton and Parker, in Washington to specifically discuss the merger and O'Hare modernization. Parker had been identified as the executive who would run the merged airline.

"We thought it critical that we hear the commitments we care about from Parker — which should occur on 10/24 in DC," Steve Koch, the deputy mayor, wrote in an email.

The day before that meeting took place, Emanuel sent his signed letter calling on the Justice Department to drop its "ill-conceived lawsuit" blocking the merger. The next day, Emanuel's calendar shows the mayor had lunch at the St. Regis hotel in Washington with Parker, Horton and Ris.

After lunch, the mayor headed to the White House for meetings with then-President Obama, his chief of staff and then-Transportation Secretary Anthony Foxx, according to Emanuel's calendar. Within weeks, the Justice Department settled with the airlines, allowing the merger to go forward that December.

In early 2014, Emanuel received $53,000 in political contributions from 10 American Airlines executives, including two maximum $5,300 contributions from Parker and Ris. The Tribune first reported Emanuel's support for the merger, the meetings with airline officials and the campaign contributions American Airlines executives made to the mayor as part of the newspaper's 2015 investigation into Emanuel's campaign fundraising.

None of the four airline executives and lobbyists who had contact with Emanuel and his staff on the merger has registered as a lobbyist in Chicago, records show. If city ethics officials were to find them in violation and fined all four from the point each contacted the mayor, fines for the group could total up to $3.6 million because their contact with Emanuel and his administration dates back more than three years.

Business pitches to Emanuel raise prospect of potential lobbying violations Hal Dardick and Bill Ruthhart

Found within the thousands of emails Mayor Rahm Emanuel released from his personal accounts are plenty of pitches from people looking to do business with City Hall.

If the Chicago Board of Ethics were to conclude that type of contact is lobbying and those individuals did not register with the city,...

Found within the thousands of emails Mayor Rahm Emanuel released from his personal accounts are plenty of pitches from people looking to do business with City Hall.

If the Chicago Board of Ethics were to conclude that type of contact is lobbying and those individuals did not register with the city,...

(Hal Dardick and Bill Ruthhart)

"None of these discussions triggered a requirement to register as a lobbyist with the city of Chicago," American Airlines spokesman Matt Miller said in a statement on behalf of Parker, the airline's current CEO. "Instead, the conversations focused on the local benefits of the merger between American Airlines and US Airways."

Horton did not respond to requests for comment through the private equity firm Warburg Pincus, where he's currently employed. Ris, who has retired from American, did not respond to a message seeking comment. Landau did not respond to requests for comment.

Electric trucks

The airline merger wasn't the only time Landau reached out to Emanuel and his administration on behalf of a business, records show. She also exchanged emails with Emanuel about Smith Electric Vehicles, a Kansas-City based company that manufactures electronic trucks and buses.

In November 2012 — six months after Landau first reached out to Emanuel about Smith Electric — the mayor announced the city would be offering the "nation's leading incentive program" to encourage private and public fleets to switch to electric trucks, setting aside $15 million. The next day, Emanuel said Smith Electric would open a manufacturing facility in Chicago, creating hundreds of jobs pending a final city incentive package.

By February 2013, Emanuel had sent a message to Landau from one of his personal email accounts, asking: "Can u please talk sense to the smith electric folks." Landau responded by forwarding a message to Smith Electric executives, relaying Emanuel's frustration.

"We've reached the end of the road w/Rahm + co.," Landau wrote. "I've been told in no uncertain terms, the Mayor now feels insulted and frustrated by the unending delays, and he is perilously close to writing off this effort."

Smith never opened a manufacturing facility in Chicago. Landau and Smith Electric executives did not respond to requests for comment.

Wrigley security

Also surfacing in Emanuel's personal emails was a March 2016 email from Cubs chairman Tom Ricketts to the mayor saying: "I need to get on your calendar about moving the ball forward on some of our security issues. . . . In addition to security, we need a few minutes on other issues related to the development." The mayor's calendar shows he met with Ricketts in his City Hall office about a month later.

The Ricketts family was moving forward with the renovation of Wrigley Field as the City Council and mayor were still trying to fashion rules for an outdoor plaza the team was building next to the stadium.

At the time, the Cubs and U.S. Rep. Mike Quigley had expressed concerns about security around the ballpark and had called on the Emanuel administration to close Clark and Addison streets and Waveland and Sheffield avenues on game days. The mayor opposed the idea, but did allow protective barriers to be installed in streets around the ballpark.

Ricketts has not registered as a lobbyist, and his spokesman Dennis Culloton said "the team believes it properly registers individuals who lobby on behalf of the team when required to do so."

Culloton also said the Cubs had "reviewed the lobbying ordinance and do not believe a change in current reporting is required." Culloton said to the best of his knowledge Ricketts had not been contacted by the ethics board. If the panel were to find Ricketts in violation of ethics rules, he could face a fine of up to $239,000, because a year has passed since he contacted Emanuel.

Canary, the ethics expert, did not review the Ricketts email. Asked about a situation in which someone emails a city official to meet about a topic the government could take action on, Canary said her view is that would qualify as lobbying.

"If that was me," she said, "I would say, 'Have you registered?'"

United O'Hare gates

As Emanuel pushed last summer to add gates at O'Hare, attorney William Singer emailed the mayor on behalf of United Airlines with a letter from the company to Aviation Commissioner Ginger Evans.

"It fully explains United's proposal and makes clear that, while this proposal reflects short term, but significant growth for O'Hare, United is fully committed to the city's long term growth and expansion plans," Singer wrote.

Emanuel replied: "Got to be honest reflected on our call. I do not know how else I can respond to a call with a verbal explanation of a concept except present to ginger," he wrote. "If you all expected yippie lets go you got the wrong mayor."

The mayor's office did not provide a copy of the letter, citing an exemption in public records law. However, Collins, the mayor's spokesman, said the document had to do with negotiations on adding gates and modernizing O'Hare. Two weeks after Singer's email, Emanuel held a news conference at O'Hare to announce that major airlines had agreed to build up to nine new gates at the airport that would be paid for with $300 million in airplane ticket fees.

Records show Singer was not registered as a city lobbyist at the time, but he's a Chicago government veteran. He was 43rd Ward alderman in the early 1970s. In a 1990 story about how Mayor Richard M. Daley's allies had won the spoils of city lobbying, the Tribune reported that Singer had been paid $115,000 by United.

After not registering as a city lobbyist since 2013, Singer filed lobbying paperwork for United on Feb. 28. If the ethics board were to find he violated lobbying rules and fined him from the first contact, Singer could face up to $156,000 in penalties because eight months have passed since he emailed Emanuel.

Singer, who was registered a federal lobbyist on behalf of United at the time he contacted Emanuel, did not respond to requests for comment. United spokeswoman Megan McCarthy declined to say whether the airline had been contacted by the ethics board but said the company was "reviewing this closely."

Singer has given $7,500 to Emanuel campaign committees, and United Airlines employees have contributed $128,000 to the mayor's campaign fund.

Real estate and friends

Also among the mayor's personal emails were several messages from longtime friend Paul Levy, who often sent various ideas on city government and has given a $5,000 campaign contribution.

In August 2014, he emailed the mayor about his development firm's project in Avondale, noting he was trying to arrange a federal low-interest loan under a program the city administers with federal approval.

Emanuel responded by referring Levy to the city's top planning official. Levy, who declined to comment, has not registered as a lobbyist. If the ethics board were to find Levy violated lobbying rules, he could face a fine of up to $640,000, because more than two years have passed since his contact with the mayor.

In December 2011, Emanuel received another email from a longtime friend on a real estate deal — Jim Abrams, chief operating officer of Medline Industries. He's married to Wendy Mills Abrams, whose family owns Medline and has contributed more than $211,000 to Emanuel-allied campaign funds since 2010.

The city purchased the former Michael Reese hospital property from Medline in 2009 under then-Mayor Daley, who envisioned the site as the home of a future Olympic Village under the city's failed bid for the 2016 games.

In his email, Abrams discussed terms of refinancing the loan Medline provided to the city to buy the property. Abrams suggested a 6 percent rate on a deal that originally came with a 7.5 percent rate — a suggestion close to the 5.95 percent the city eventually reached in a 2012 deal. "Wonderful seeing you and thank you," Abrams wrote. "Love to family."

Although Abrams agreed to a lower interest rate, the city structured the deal so that Medline did not have to pay taxes on the profits as it did originally — an arrangement that could boost the company's profit in the end. Under the city's ethics law, altering the terms of a public loan could qualify as an "administrative action."

Records show Abrams, who did not respond to requests for comment, has never registered as a city lobbyist. If the ethics board were to find Abrams violated lobbying rules, he could face a potential $1.3 million fine because more than five years have passed since his contact with Emanuel on the issue.

In April 2015, Abrams contacted Emanuel on another matter, forwarding the mayor a letter from "one of my dearest friends in the world," Douglas Bank, chief operating officer of Phoenix Electric Manufacturing Co. Bank was seeking a small manufacturer's exemption from the city's minimum wage ordinance.

In the email, which Abrams forwarded to Emanuel, Bank asked Abrams to "facilitate a meeting with the Mayor or Chief of Staff so that we can make our case." Bank also said he'd "been working diligently with our Alderman" James Cappleman, 46th.

Bank, who did not respond to requests for comment, has not registered as a lobbyist. If the ethics board were to find Bank violated lobbying rules, he could face a fine of up to $458,000 since his contact with Cappleman dates back to 2015.

bruthhart@chicagotribune.com

hdardick@chicagotribune.com

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