Chicago ethics officials have ruled five more people broke city ethics laws by lobbying Mayor Rahm Emanuel through his personal email account.

The city’s Board of Ethics also leveled fines of $2,500 against two men — an Emanuel donor and the husband of an alderman — it ruled last month illegally lobbied Emanuel without being registered lobbyists.

In another development, the board released a list of more than two-dozen lobbyists it said had failed to undergo required lobbyist training and could be subject to fines of up to $750 for every day they are in non-compliance. Among those on the list is Chicago Cubs Chairman Tom Ricketts, who first filed as a lobbyist earlier this year, according to city records.

Ricketts spokesman Dennis Culloton said the Cubs owner had completed the required training before the city’s deadline. At the same time, Culloton confirmed that Ricketts’ decision to register as a lobbyist came in response to a board inquiry about a March 2016 email he sent the mayor in which he sought a meeting to discuss several issues, including development projects near Wrigley Field.

“Tom Ricketts and the Cubs were contacted by the board and cooperated fully and proactively with the Board’s review. The Board recently made a ‘no probable cause’ determination regarding any improper lobbying by Tom Ricketts or the Cubs,” Culloton said in a statement. “Neither Tom or the team has been fined or sanctioned in any manner. While we believe he is under no legal obligation to do so, Tom has voluntarily registered as a lobbyist.”

The two lobbyists who were fined Wednesday could have each faced penalties of up to $500,000 under city law. But Ethics Board Chairman William Conlon said the board levied only modest fines because the law gives the board wide  latitude and it wasn’t seeking to be punitive.

The board’s rulings bring to eight the total of individuals it has determined have violated the law by trying to influence Emanuel on government actions through contacts via his personal email. The electronic conversations were made public after a settlement in late 2016 of a Better Government Association lawsuit against the city.

The board would not release the names of the additional five individuals it said violated the law. It is expected to soon release most of those names once the individuals involved are notified of the board’s decision, Conlon said. In those cases, the board said violators will be fined between $1,000 and $25,000.

The board also dismissed four others cases that initially had warranted “probable cause” letters for potential violations.

Last month, the board ruled two men — Jim Abrams and Alan King — broke the city’s ethics rules for trying to influence the mayor on City Hall issues without registering as lobbyists. Abrams is the chief operating officer of medical supply giant Medline Industries and a contributor to Emanuel’s political campaign funds. And King is husband of 4th Ward alderman Sophia King.

City ordinance allows such infractions to be fined at a rate of $1,000 a business day, with the clock starting five business days after the infraction occurs and ending when the matter is cleared up.

“We felt like we had discretion under the statute to make adjustments as we needed to,” Conlon explained.

Early in 2017, the board imposed $92,000 in fines against former Obama White House official David Plouffe and his then employer Uber for a 2015 email exchange in which Plouffe pressed Emanuel to have the city ease up on regulations related to the ride sharing giant. Plouffe was not a registered lobbyist at the time, but did file papers with the city months later.

The latest fines were much smaller, Conlon explained, because the board did not consider the violators to have acted in bad faith.”Was it intentional?” Conlon said in explaining the board’s rationale. “Was it malicious? Were they scheming? The answer was no.”

In Abrams’ case, the ethics board said he violated city ethics laws by forwarding an email from one of his friends to Emanuel on April 28, 2015.

The initial message was from Douglas Bank, an executive of Phoenix Electric Manufacturing Company who Abrams described to Emanuel as “one of my dearest friends in the world.” Bank was seeking an exemption from a Chicago ordinance raising the minimum wage to $13 by 2019 and asked Abrams if he could “facilitate a meeting with the Mayor or Chief of staff” so Bank could make his case.

The ethics board noted the forwarding of the email, which was sent to Emanuel’s personal email address, was an attempt to influence an administrative action.

State campaign records show Medline officials have donated $211,000 in campaign funds to the mayor’s campaign funds. Most of the money came from Abrams himself.

In Alan King’s case, the ethics board cited the attorney for an email sent to the mayor on May 21 2015, in which he asked the mayor for help with planned construction issues he thought would interfere with a music event in which he was a business partner.

In addition to being an attorney and partner at the Drinker Biddle & Reath law firm, King moonlights as house music DJ.

In his email, King told the mayor he was having “a bit of a crisis situation” with a music event planned for Jackson Park. King asked Emanuel “to help at least to broker a solution.”

Emanuel responded with a suggestion to contact Mike Kelly, the park district’s CEO and a few weeks later King circled back to the mayor to tell him that the problems were being worked through. “I think everything is going to work out,” King wrote.

King closed his note to the mayor by saying, “Please say hello to Amy (Emanuel’s wife) from Sophia and me.”

Emanuel appointed Sophia King to her aldermanic post last year to fill a vacancy.

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.