Exclusive: Chicago PD employee sues city after suspension for ‘F*** Trump’ Facebook post at ‘No Kings’ protest

A high-ranking civilian employee with the Chicago Police Department is suing the city after he was suspended for 14 days without pay for a pair of posts he made to his personal Facebook account while attending a “No Kings” protest last year.

Mike Milstein, the deputy director of CPD’s Office of Equity and Engagement, posted the messages during the October 18, 2025, demonstration while he was in Denver for a conference, according to a federal lawsuit reviewed by The Independent.

One of the posts was an illustration of people’s hands holding up hearts, and the words: “NO KINGS IN AMERICA.” The other was a photograph of the No Kings crowd outside the Colorado State Capitol, with one raising a hand-lettered sign reading: “ELECT A CLOWN, EXPECT A CIRCUS.” Milstein, who also heads up the department’s Office of Victim Services, added the hashtags “#NoKingsDay” and “#F**kTrump,” the complaint states.

The nationwide No Kings action took place in more than 2,700 locations across the United States, drawing between five million and seven million attendees pushing back against the overreach and excesses of the second Trump administration.

Although Milstein was in town for work, the complaint says he was off the clock at the time and that he made the posts using his personal device. Neither post made any reference to CPD, the City of Chicago or Milstein’s job. But after CPD’s Bureau of Internal Affairs received an anonymous letter about the posts, Milstein was suspended for two weeks, without pay.

“Neither posting attacked, ridiculed, or was directed at any private citizen, any co-worker, or any member of the public,” Milstein’s complaint argues. “Neither posting employed language beyond what was necessary to convey Milstein's disapproval of the President and his support for the demonstrations, and the language he used was the language of the demonstrations his postings depicted and endorsed.”

Criticism of the president is “core protected expression” under the First Amendment, and a municipal employer “may not maintain a standing prohibition that sweeps in the political speech of thousands of employees” if it doesn’t impact the way they do their jobs, according to the 38-page complaint, which was filed September 14 in Chicago federal court.

It says Milstein “intends to resume” posting messages on social media that are critical of Trump, specifying that they will include “photographs and images of public demonstrations concerning national political questions that he attends or observes,” “statements criticizing the President of the United States by name,” and “political statements containing profanity.”

“He intends to attend or observe further demonstrations of that character, and expects further such demonstrations to occur,” the complaint states. “He would post such content now but for the challenged provisions and the discipline imposed under them, and he has refrained from doing so since the suspension.”

In an email on Wednesday, a spokesperson for the City of Chicago told The Independent, “We do not comment on pending litigation.”

Milstein began working for the Chicago Police Department in 2020, in CPD’s Office of Community Policing, according to an official bio. In 2024, he stood up the department’s Office of Equity and Engagement, working to build bridges with marginalized communities, and also took over the department’s struggling Office of Victim Services.

As his complaint emphasizes, Milstein – who has received five departmental awards in six years – is not a sworn police officer.

“He exercises no police powers, makes no arrests, carries no weapon, and is assigned no [badge] number,” the complaint explains. “He performs no operational police function. He does not respond to calls for service, is not deployed to any police operation, and is not charged with maintaining public safety or order in the field.”

Further, it says none of Milstein's duties involve national politics or the president, and nothing in his employment agreement prohibits him from criticizing elected officials. So, when Milstein went to Denver last October for an International Chiefs of Police gathering, he went to one of the thousands of No Kings rallies happening that day.

Some five weeks went by, without a word from anyone about the two posts Milstein had made while there. Then, on November 26, CPD’s Bureau of Internal Affairs received an anonymous letter with printed copies of the posts, claiming they violated CPD General Order G09-01-06, which governs members’ social media use.

The following month, Internal Affairs opened an investigation, and took a statement from Milstein, the complaint goes on.

On January 8, 2026, former CPD Supt. Larry Snelling ordered Milstein suspended by for two weeks without pay, following a finding by Internal Affairs that said he “failed to seek Department guidance” before making the Facebook posts. However, the complaint asserts, the Internal Affairs report did not find that the postings caused any “disruption of any Department operation,” a single “complaint by any Department member,” or “harm of any kind to any interest of the Department,” or the public.

“That the Department paid for his travel to a conference does not convert his personal political expression into work performed for his employer,” the complaint states.

Other police departments have given employees, even sworn officers, far more latitude in governing their political speech.

In Anne Arundel County, Maryland, a cop who participated in the January 6 pro-Trump Capitol riot, in which five people were killed, including at least one police officer, was suspended with pay, then reinstated to “full duty status” after the department’s Office of Professional Standards found “no violations of agency policies or applicable laws.”

Two correctional officers, also from Maryland, took part in the January 6 insurrection, as well, and were suspended after being caught on video at the Capitol that day. But they, too, were reinstated following an internal review that exonerated them from any discipline “based on the rights afforded to the officers by law.”

In a third case, Trump himself was responsible for the reinstatement of two Washington, D.C., police officers who had been convicted and sentenced to prison for covering up a man’s death in an unauthorized vehicle pursuit. However, they were both returned to duty in March 2025 after Trump pardoned the two officers, which the ACLU called “an affront to public safety in the District.”

Milstein, according to his complaint, “faces a credible threat of further discipline if he resumes such speech,” and says any future punishment will be stricter because of the existing black mark already in his permanent record.

He is now seeking compensatory damages from the City of Chicago, including back pay for the 14 days of lost salary, plus punitive damages from Snelling for violating his “clearly established First Amendment rights.”

He is also demanding that his disciplinary history be voided, and wants reimbursement for his legal fees and court costs, plus interest.

Milstein and his attorneys did not respond to multiple requests for comment.