David Plouffe, Barack Obama’s 2008 campaign manager, was fined $90,000 by the Chicago Board of Ethics in a 5-0 vote for improperly lobbying Mayor Rahm Emanuel on behalf of Uber Technologies.

The San Francisco resident was fined $1,000 a day for the 90 days he used personal email accounts without being a registered lobbyist to lobby Mayor Emanuel, former Chief of Staff to President Barack Obama, to allow Uber to make unlimited ride-share pick-ups at Chicago’s Midway and O’Hare airports. Plouffe and Emanuel had worked together during Obama’s first campaign.

The City of Chicago had operated a lucrative business auctioning off taxi cab medallions for a minimum of $360,000 per medallion. That explained why the base fare for a Chicago taxi ride was $ 3.25 for the first mile and $ 2.25 for each additional mile. The added medallion cost also explained why the fare for a taxi cab ride from the downtown Chicago Loop to O’Hare was $36, plus tip, compared to just $28 for the same passenger to take an Uber ride.

After Mayor Emanuel announced that he was authorizing Uber and Lyft to make trips formerly restricted to cab -nly pickups at O’Hare and Midway, as well as at the McCormick Place convention center, the American Federation of State, County and Municipal Employees (AFSCME) called a strike of Chicago’s 12,000 taxi drivers on October 6, 2015. The union wanted to stop ride ride-sharing, or force Uber to pay a $5 surcharge to the City to level the cost with taxis, according to the CBS local affiliate.

Community Digital News (CDN) had been reporting that Rahm Emanuel had a family conflict regarding ride-sharing in Chicago, because his brother Ari Emanuel had a financial interest in the company.

As a vice president of policy and strategy for Uber, Plouffe began communicating on behalf of Uber through the mayor’s personal email accounts. Plouffe was concerned about the surcharge fee and the city requirement that the Uber vehicles that make airport pickups would be required to include signs designating those vehicles had paid the fee.

CDN reported that beginning November 25, 2015, Plouffe sent the following emails to Emanuel:

“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.”

“Coming to you because of their severity that would prevent us from operating. We were all set to announce Monday we were beginning pickups.”

“Sure this comes as much of a surprise to you as us, since there was an agreement in place.”

Emanuel was traveling and referred Plouffe to a pair of his top aides, but the private email chains were subsequently released when Emanuel settled a lawsuit filed by the Better Government Association. That caused the Board of Ethics to cross-check the names of those using the mayor’s private accounts to lobby for administrative or legislative action to see if they were registered as lobbyists.

Plouffe is one of about 30 individuals that the ethics board has designated as using Rahm Emanuel’s personal emails to lobby him regarding city issues. The Chicago Board of Ethics chairman William Conlon responded to the Chicago Sun Times’ questions about individuals other than Plouffe others being fined by stating, “It is the only fine we have publicly announced,” hinting there will be more parties fined.