A former Uber senior executive who once served as Barack Obama's campaign manager has been fined $90,000 by the Chicago Board of Ethics for illegally lobbying Mayor Rahm Emanuel on behalf of the ride-sharing company.

The board voted 5-0 to find that David Plouffe violated city ethics rules by failing to register as a lobbyist after contacting Emanuel to help the company on regulations for picking up travelers at Chicago's two airports.

Plouffe's lobbying violation only became public after Emanuel in December released hundreds of personal emails related to public business under the pressure of two open records lawsuits alleging the mayor violated the state's open records law.

Included was a message Plouffe sent to the mayor Nov. 20, 2015.

"Assume both of us thought the airport issue was settled and we would never have to discuss again, but unfortunately two significant new hurdles were introduced," wrote Plouffe, the political strategist who managed Obama's 2008 presidential campaign and in 2015 was Uber's senior vice president of policy and strategy. "Coming to you because of their severity that would prevent us from operating. We were all set to announce Monday we were beginning pickups."

Plouffe, who like Emanuel served in the Obama White House, went on to describe concerns Uber had about pickup fees and the requirement to display an airport pickup placard in Uber vehicles.

"Sure this comes as much of a surprise to you as us, since there was an agreement in place," Plouffe wrote. "I hope we can resolve these issues before the holiday. Our team is eager to move forward and begin operating at the airports in advance of the Thanksgiving holiday — as you called for and we'd like to deliver on the schedule for you."

Emanuel, who was traveling at the time, quickly responded.

"Please speak to Negron and David on my staff. Impossible for me to address from China," wrote Emanuel, referring to Michael Negron, the mayor's chief of policy, and David Spielfogel, then his senior adviser.

Plouffe's communication with Emanuel came as City Hall had weighed how to regulate the emerging ride-share industry, eventually settling on rules that are less stringent than those placed on the city's taxi companies. The mayor's brother, Hollywood talent agency CEO Ari Emanuel, is an investor in Uber.

Last June, aldermen attempted to pass stronger regulations on ride-sharing companies to even the playing field for the taxi industry, only to have them watered down. When aldermen pushing for the stronger rules, which included fingerprinting drivers, tried to use a parliamentary maneuver to delay the action, Emanuel threatened to adjourn the City Council meeting. In the end, the watered-down version Emanuel preferred remained intact.

In its final determination to issue its reprimands, the Board of Ethics stated that both Uber and Plouffe "do not dispute the allegations" of violating the city's lobbying ordinance or contest the possibility of a fine. Uber and Plouffe argued he should only be subject to a $1,000 fine, according to the ethics board.

The city's ordinance, however, calls for a $1,000 fine for each lobbying violation and that "each day that a violation continues shall constitute a separate and distinct offense to which a separate fine shall apply." The board handed down a $90,000 fine because Plouffe did not register until April 13, 2016, long after the five business day requirement for registration after he first lobbied Emanuel. The fine reflects the 90 business days he was not registered after first contacting the mayor.

"Mr. Plouffe and the 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 every day during this period," the ethics panel wrote in its determination. "The board rejects this argument."

The board said 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."

Plouffe could not be reached for comment.

Plouffe Scott Strazzante / Chicago Tribune

David Plouffe speaks before United States President Barack Obama appears at campaign fundraiser at Navy Pier in Chicago, IL on April 14, 2011.

David Plouffe speaks before United States President Barack Obama appears at campaign fundraiser at Navy Pier in Chicago, IL on April 14, 2011.

(Scott Strazzante / Chicago Tribune)

The Board of Ethics fined Uber $2,000, the penalty the city's ordinance requires for each act of hiring a lobbyist who violates the city's lobbying laws. Uber spokeswoman Molly Spaeth said the company accepted the ethics panel's decision.

"We work hard to ensure our registrations are accurate and up to date," Spaeth said in an emailed statement. "We regret that in this instance we made a mistake and we will comply with the board's assessment."

The start date the ethics board used to tally Plouffe's fine was the Nov. 20 date of the email, but the lobbyist indicated in his message he had communicated with Emanuel previously on the topic by referencing that the two likely thought the ride-share regulations were an issue "we would never have to discuss again."

Asked when Plouffe began to reach out to Emanuel personally on behalf of Uber, Spaeth responded, "I don't have any additional details to share at this time."

Emanuel released the email from Plouffe as part of a settlement with the Better Government Association that sought official emails from the mayor's nongovernmental accounts. The settlement was announced in December, 12 days after the Chicago Tribune won a round in its ongoing lawsuit alleging the mayor violated the state's open records laws by refusing to release communications about city business Emanuel conducted through personal emails and text messages.

In the Tribune case, a judge has ordered Emanuel to produce an index of certain emails and text messages the mayor sent and received on his personal devices. No such requirement was part of the BGA settlement, which relied on Emanuel's personal attorney and City Hall's Law Department — not an independent party — to determine which emails were public records.

bruthhart@chicagotribune.com

hdardick@chicagotribune.com

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