A former alderman who once bucked the Democratic machine and an internet pioneer turned venture capitalist are among the latest people to be hit with city ethics fines for illegally lobbying Mayor Rahm Emanuel through his personal email account.

The city Board of Ethics levied a fine of $25,000 on William Singer, a onetime city council maverick who unsuccessfully sought to topple the late Mayor Richard J. Daley in the 1975 mayoral race. Separately, the panel slapped a $2,000 fine on Marc Andreesen, the inventor of the Netscape internet browser.

Those were among the latest group of five individuals the ethics panel said had violated city law and been fined for attempting to influence Emanuel or other officials through emailed contacts that became public after the settlement of a Better Government Association lawsuit against the city.

The BGA in late 2016 gained release of thousands of pages of emails from Emanuel’s personal account, which the watchdog group argued he had improperly used to conduct public business.

The new sanctions announced by the ethics board raise the total to eight of those fined for improper lobbying by the board in connection with the Emanuel emails. The largest of those fines, $92,000, was imposed on former Obama White House official David Plouffe and ride-sharing giant Uber for which Plouffe worked when he contacted Emanuel in 2015.

Singer was cited for lobbying Emanuel last summer on behalf of United Airlines about efforts to expand gates at O’Hare International Airport. United was also hit with a $2,000 fine, the maximum that can be imposed on an employer that could benefit from improper lobbying.

Along with Singer and Andreesen, the latest batch of those fined for illegal lobbying included Greg Prather, president of JLL real estate, and Anthony Davis, president of Linden Capital Partners.

Prather, who was fined $2,500, emailed Ald. Daniel Solis, 25th, chairman of the City Council’s zoning committee, in October 2016 regarding redevelopment work at the old Chicago post office. The email to Solis asked the alderman to intervene to help reduce inconvenience caused by repair work to Amtrak tracks running under the abandoned postal facility. A staff member for Solis forwarded the email to Emanuel.

Davis wrote to Emanuel in December 2014 about a zoning matter involving a triathlon training center that had been moved due to CTA work. Davis was fined $2,500.

A fifth individual was fined $1,000 but the ethics board declined to identify the individual, contending the infraction occurred during a time when city’s ethics laws prohibited disclosing such names. The law was later changed.

The ethics board also recently leveled fines of $2,500 each against Emanuel donor Jim Abrams and Alan King, the husband of 4th Ward Ald. Sophia King for lobbying Emanuel through the mayor’s personal email address.

Jared Rutecki was an investigative reporter and data coordinator at the Illinois Answers Project (previously known as the Better Government Association) from 2016 to 2023.