A close friend of and heavy donor to Mayor Rahm Emanuel, as well as the husband of a Chicago alderman, face hefty fines for lobbying the mayor through his private emails but failing to register as lobbyists.

Alan King, husband of Ald. Sophia King (4th), and James Abrams — whose wealthy North Shore family owns Medline Industries and sold the city the Michael Reese Hospital site —  are the latest targets of the reinvigorated Board of Ethics.

Alan King is a house-music disc jockey and Chicago attorney who is a close friend and basketball buddy of former President Barack Obama. In part, that’s how Sophia King came to the attention of Emanuel, who was Obama’s first White House chief of staff.

The email correspondence with Emanuel that drew the ethics board’s attention involved a permit to hold a “House Music Picnic” in Jackson Park. The event was being threatened by construction on the site.

“I have a bit of a crisis situation with the Chicago Park District . . . due to some construction work the park district has allowed on our picnic site (despite permitting the site to us),” King wrote to the mayor. “I apologize, but it is a very serious situation for me and my business partners, and I think you might be able to help at least to broker a solution.”

Emanuel asked King if he had contacted Park District Superintendent Mike Kelly. The mayor also forwarded King’s message to a top aide.

Two weeks later, King emailed the mayor again to say, “I think everything is going to work out.” He added, “Please say hello to Amy [Rule, the mayor’s wife] from Sophia and me.”

In an emailed statement, King said he “expected a different outcome” for, what he called “many factual and legal reasons.”

“Along with my friends and colleagues, the Chosen Few DJs, we are committed to taking appropriate actions when necessary to protect and preserve….one of the crown jewels of the South Side,” he wrote.

Ald. Sophia King (4th) could not be reached.

Abrams got into trouble with the board for his April 28, 2015, email to the mayor seeking help for Douglas Bank, chief operating officer of Phoenix Electric Manufacturing Co. Bank, whom Abrams called “one of my dearest friends in the world,” was seeking a “small manufacturer’s exemption” from Chicago’s minimum-wage ordinance.

James Abrams

Rahm Emanuel’s close friend, James Abrams | File photo

Abrams wrote: “Whatever you decide, you decide, but I’d appreciate very much if you would hear him out.”

Enclosed was the email from Bank which read, “We have been working diligently with our aldermen…in trying to gain a small manufacturer’s exemption to the . . . minimum wage ordinance and/or seeking a determination…that ‘compensation’ as defined in the ordinance includes health insurance, pension.”

“We simply cannot pass on our cost increases to our customers . . . Puts [our company] and other small manufacturers at a competitive disadvantage.”

Abrams, Medline’s chief operating officer, could not be reached for comment on the board’s “final determination of lobbying violations.” Abrams, his wife and a top Medline executive have contributed more than $250,000 to Emanuel and to a super-PAC controlled by his allies.

Fines for both King and Abrams will be determined at the board’s meeting on July 17.

The potential fine is $1,000 a day for every day that a person failed to register as a lobbyist. The clock starts ticking five days after the contact was made.

In King’s case, that would be $750,000 and counting, since he still hasn’t registered. Abrams, who also hasn’t registered, would face a $773,000 fine.

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“I do not anticipate the board will impose the maximum fine. That would be an enormous amount of money,” Ethics Board Chairman William Conlon said Friday.

But Conlon argued that the fine needs to be “enough to send a message.”

Although the Abrams email that drew the Ethics Board rebuke is more than two years old, the Chicago Sun-Times reported in April on a more recent exchange that occurred earlier this year.

Records show that Abrams also emailed the mayor in 2011 about refinancing the Medline loan the city used to purchase the Reese property for an Olympic Village that was never built.

Under Conlon’s leadership, the revamped Board of Ethics has been shedding its longtime image as a paper tiger.

Emanuel’s private emails have provided a treasure trove of information that has allowed the board to investigate lobbying offenses it could not investigate on its own. A dozen other clout-heavy lobbyists are facing hefty fines in the continuing fallout from the massive information dump that was supposed to end Emanuel’s legal battle to keep 2,700 of his private emails concealed from public view.