A former Senior Advisor to President Obama has been fined $90,000 for violating the City of Chicago’s lobbying ordinances by communicating with Mayor Rahm Emanuel on behalf of his client without registering as a lobbyist with the city’s Board of Ethics. The unregistered lobbyist, who was a colleague of Mayor Emanuel’s during his time at the White House, was seeking to influence city rules.

The Chicago Board of Ethics learned of the violation after the Mayor released hundreds of emails due to pressure from unrelated lawsuits arguing that he had breached Illinois’s public records laws. In an email sent to Mayor Emanuel on November 20, 2015, the lobbyist crossed the strict registration threshold by attempting “to influence any administrative action” by the city, illustrating how a seemingly innocuous conversation between former colleagues—and even friends—can still trigger lobbying registration requirements.

By neither registering as a lobbyist within five business days of crossing the threshold nor filing required quarterly lobbying activity reports, the lobbyist failed to comply with the city’s rules, incurring a fine of $1,000 for each business day in violation.

Chicago, in its “Final Determination,” rejected the lobbyist’s argument that the fine should be only $1,000 for a single lobbying instance, stating “how many times one lobbies while unregistered is irrelevant to the violation or to the calculation of the fine.” The lobbyist was fined accordingly, and the client was also fined $2,000 for retaining an unregistered lobbyist.

It is important to note that this case is not just a high-profile exception. Jurisdictions, including Chicago, monitor and actively enforce their lobbying laws, resulting in fines, loss of business opportunities and other adverse consequences. This case demonstrates how lobbyist employers may suffer reputational and financial risk by not ensuring that their lobbyists—and their own organizations—are intimately familiar with lobbying regulations in various jurisdictions, which differ broadly in their lobbying registration thresholds and reporting requirements.

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