High-ranking Chicago (Illinois) police officer Mike Milstein is suing the city after he was suspended for two weeks without pay due to a social media post against US President Donald Trump. Milstein claims that the punishment violated his right to freedom of speech, and intends to openly criticize the head of the White House again, writes The Independent.
Milstein serves as Deputy Director of the Chicago Police Department's (CPD) Office of Equity and Engagement and also directs the Office of Victim Assistance. However, he is a civilian police officer: he does not carry a weapon, does not have a police badge, does not have the right to make arrests and does not participate in operational work. According to his LinkedIn page, he has been with the Chicago Police Department for more than six years.
The reason for the proceedings was two publications that Milstein posted on October 18, 2025 on his Facebook account. At the time, he was in Denver, Colorado, attending a professional conference and, in his free time, attended one of No Kings' anti-Trump rallies.
One of the publications featured an illustration with the inscription “NO KINGS IN AMERICA” (“No kings in America”), and another featured a photograph of participants in a rally at the Colorado State Capitol. The picture showed a poster “ELECT A CLOWN, EXPECT A CIRCUS” (“If you choose a clown, wait for the circus”). Milstein accompanied the publication with the hashtags #NoKingsDay and #F**kTrump.
The messages were posted from a personal device after hours and did not include references to Chicago police, city officials or Milstein's job title, the lawsuit alleges.
About five weeks later, CPD's Bureau of Internal Affairs received an anonymous letter containing printouts of the posts and a claim that they violated the department's social media policies. An internal investigation began in December.
On January 8, 2026, then-Chicago Police Superintendent Larry Snelling ordered Milstein to be suspended for 14 days without pay. An internal investigation concluded that the employee did not seek clarification from the department before publishing the posts.
However, as emphasized in the lawsuit, the investigation did not determine that Milstein's publications in any way disrupted police work, caused complaints from other officers, or harmed the interests of the department or the public.
Milstein did not agree with the punishment. On September 14, he filed a lawsuit in Chicago federal court, arguing that criticism of the president constitutes political speech protected by the First Amendment.
Despite the disciplinary action, Milstein intends to continue to publicly speak out against Trump. The lawsuit says he plans to attend political demonstrations, post photographs of them, criticize the president by name and use profanity in political publications.
The employee is seeking damages from Chicago, including pay for the 14 days of suspension, and the disciplinary record vacated. He is seeking punitive damages from former CPD Chief Snelling for alleged violations of his First Amendment rights. In addition, Milstein expects to seek reimbursement of attorney fees and court costs.
