The Arrest
As I was walking along Upper Wacker Drive, approaching Wabash, I wondered where everybody was tonight. The clock affixed to the Jewelers Building had just struck 6:00 PM, but I didn’t see anyone standing across from Trump Tower. Virtually every anti-Trump demonstration in Chicago ends with a crowd of people standing on the sidewalk above the riverwalk facing Trump Tower.
And then the helmeted Kenny, a beloved presence at countless demonstrations, road toward me on his trusty bicycle just as I was crossing Wabash. Kenny was headed to Trump International Tower and Hotel’s main entrance on Wabash, where a group of demonstrators had gathered.
I was very surprised, because for years, the Chicago Police Department has prevented demonstrators from gathering on Wabash near the Chicago headquarters of the ‘Evil Empire.’ Somewhat ominously, about a dozen CPD officers had swapped their standard-issue powdered blue shirts for non-conforming polo shirts and tees. Somebody had decided to bring in some sort of tactical squad, which meant somebody thought there might be arrests tonight. Why CPD didn’t just follow normal protocol—closing Wabash to the demonstrators—is beyond me.
As I eyed the situation, I saw 50 or so demonstrators milling about, with a several people unfurling a large yellow banner that read “No War on Iran” in front of the entrance to Trump International Hotel and Tower. Veteran activist Andy Thayer appeared to be overseeing the operation. Within moments, he was engaged in a conversation with CPD Officer Syed Quadri, the officer seemingly in charge of CPD’s response. Interestingly, the uniforms identified the officers as belonging to the Near North District, although the bicycle cops were from the Critical Incident Response Team (“CIRT). Normally, officers from CIRT police downtown rallies and marches.
Thayer was holding a piece of paper he said contained the text of Illinois Statute Section 5/21.1-2 (Chapter 38). That statute addresses residential picketing, providing:
A person commits residential picketing when he or she pickets before or about the residence or dwelling of any person, except when the residence or dwelling is used as a place of business. This Article does not apply to a person peacefully picketing his own residence or dwelling and does not prohibit the peaceful picketing of the place of holding a meeting or assembly on premises commonly used to discuss subjects of general public interest.
Thayer subsequently argued that the prohibition did not apply to the group because Trump Tower is not used exclusively as a residence or dwelling. Given that the tower houses a hotel, meeting and conference rooms, restaurants, bars, and a hotel, Thayer’s position is a legally defensible one. CPD, however, might counter, arguing that the tower includes individual deeded residential dwellings that do not constitute businesses. Does the statute focus on the entire building, or on deeded individual units within the building? I did not research whether there is any dispositive case law.
Given Trump Tower’s mixed uses, I can posit any number of circumstances that make the application of Section 5/21-2 problematic. Imagine if the KKK held an annual convention at the hotel. Or, if the DNC held its 2028 national nominating convention in Chicago, designating the hotel as the convention’s official headquarters. Shouldn’t people be allowed to stand across the street expressing their views? Given the relatively small footprint in front of the hotel, CPD would likely argue that a large demonstration raised public safety considerations.
In any event, Officer Quadri eventually identified himself to the crowd, and then announced that the gathering was an illegal one. He suggested that the demonstrators march across the bridge, and then gather on the walkway facing Trump Tower—the usual spot for anti-Trump demonstrations, which is arguably within sight and sound of the Trump Tower, although I suspect Thayer and others would dispute that conclusion.
The demonstrators responded by then crossing Wabash to gather in the plaza outside the AMA Building (formerly the IBM Building), which faces the entrance to the Trump International Hotel and Tower. The change of venue did not satisfy CPD. Once again, a CPD officer gave Thayer a warning that he would be arrested if he did not follow police instructions—this time the officer was Near North Commander Christopher Bielfeldt. Thayer pointed out that in his view, the Trump International Hotel and Tower is not a residential building within the meaning of the statute because it is not exclusively residential. Thayer specifically referenced the hotel operations.
Commander Bielfeldt noted that Thayer and the other demonstrators were now standing on private property—the AMA Plaza. It is not at all clear that Thayer was standing on private property after he had crossed the street. To make that determination, I would need to review the deed for the AMA Plaza. Running along the plaza is a metal strip embedded in the plaza’s quartz-surfaced plaza. The strip may be structural given that the plaza is elevated above the street below, but it also may mark the plaza’s boundary line. Moreover, is the plaza public or private property for First Amendment purposes if the developer granted an easement for pedestrian traffic?
At the time, I did not focus on which side of the strip Thayer was standing. If the strip does mark the boundary line and Thayer was on the east side of the strip at the time of his arrest, he presumably was not standing on private property. As I have suggested, if he was standing west of the strip, we have an interesting legal question as to whether Thayer was standing on private property once any easement previously granted to the city is factored into the equation.
I should note that Thayer and Commander Bielfeldt were civil to each other. Thayer did not yell or swear; he just stated his position and asserted what he believed to be his rights. Bielfeldt gave Thayer a warning and time to “retreat,” but Thayer stood his ground. When he was arrested, the officers were firm, but they certainly didn’t manhandle or attempt to rough Thayer up.
After Thayer was placed in handcuffs, several officers led him to and then placed him into a squad car for transport. Within a minute or two, the squad car took Thayer to wherever they take people who are arrested during demonstrations.
I plan to ask Thayer about the disposition of the matter next time I see him. I assume he was released within hours of the arrest. I also suspect he received some sort of ticket, with the option to either pay or contest it in court. One thing is for sure: he did not resist arrest. By all outward appearances, he was cool, calm, and collected. Had I been Thayer, I would have shit myself before they had me in the back of the squad car.
I do wonder whether Thayer arrived at today’s demonstration planning or even hoping to to be arrested. Since Donald J. Trump became president, people have wanted to demonstrate in front of the Trump International Hotel and Tower, but CPD has prevented them from doing so, citing Illinois Statute Section 5/21.1-2 (Chapter 38). Knowing that, Thayer and company must have known that CPD would ask them to vacate the area. In fact, I am surprised CPD allowed the group to even gather. As in the past, CPD could have denied access to the demonstrators by strategically placing officers at what might be described as checkpoints.
I left the demonstration with one question: Will Thayer contest the arrest, hoping that a court rules that CPD’s limitations violate the First Amendment? Stay tuned.
Following Thayer’s arrest, the group marched south over the Wabash Bridge. They then took up position on Upper Wacker downwind from the Trump Tower. With two exceptions, several people then delivered rather anemic remarks. It was the representative from the Palestinian Community who delivered the evening’s incendiary remarks. For my money, he focused a bit too much on Gaza given that the demonstration was an anti-Iran War demonstration, but the demonstrators didn’t object. Alderman Byron Sigcho-Lopez delivered the closing remarks. Surprisingly, he was not as animated as he usual is, but he spoke his mind.
Had it not been for Thayer’s arrest, this demonstration would have been largely forgettable. Photographically, it was anything but forgettable given the beautiful light illuminating the demonstrators and the CPD officers.
As for Thayer, as a veteran activist, he knows what he is doing. Nevertheless, whenever I see someone risking arrest by pushing the boundaries, I always find myself mumbling under my breath, “It isn’t worth it. Back off.”
I admire the people who came out to express their views, but late afternoon demonstrations during the workweek are pretty low key affairs that don’t draw large numbers. Thayer certainly brought game to today’s demonstrating, making it far more interesting than it otherwise would have been.
For video of the events leading up to Thayer’s arrest and the arrest, click here.
[Nothing in This Post Is or Should be Taken as Legal Advice. Click on an Image to Enlarge It. The Images Are Not Necessarily in Exact Chronological Order]
Preventing the Demonstrators From Rushing the Lobby
CPD Asking the Demonstrators to Move
Singing As He Complies With the CPD Order to Move
Setting Up Across the Streeet From Trump International Hotel and Tower
Near North Commander Christopher Bielfeldt Asking Andy Thayer to Move
Officer Syed Quadri Observing the Scene
Trying to Reason with Andy Thayer
Placing Andy Thayer Into Custody
Under Arrest
Adjusting the Handcuffs
Heading to the Squad Car
Being Led Away
The Televsion Stations Getting the Arrest on Video
About to Close the Squad Car's Door with Thayer Inside
Taking Andy Thayer Whereever They Took Him
The Aftermath
Beginning to Head Across the Wabash Bridge
Maintaining the Barrier
Being Asked to Move
Heeding the Instructions to Move, Thereby Avoiding Arrest
Beginning to Move
Does the Metal Strip Separate Public from Private Property? What About Easements Permitting Pedestrian Traffic?
"Viva Viva Palestina Libre!!"
Demanding that Trump Stop the War Machine
The Afternoon Light Illuminating the Scene
Watching the Demonstrators Depart
Passing The Coco Bar
CPD Following the Demonstrators Across the Wabash Bridge
Pedestrians Passing By
Covering Irv Kup's Crotch
An Unflattering Comparison
Longtime Activist Linda Loew Speaking Her Mind
A Leader of Chicago's Palestinian Community Addressing Both the War in Iran and the One In Gaza
Yiddish for the Fight for Justice
Found a Comfortable Perch
Another Speaker Expressing Her Outrage
One Sign Putting Things In Perspective
Alderman Byron Sigcho-Lopez Bringing the Speeches to a Close with His Typically Fiery Remarks
Telling Donald J. Trump to End the War on Iran
Using WWII Symbolism to Call Out Donald J. Trump
Ready to Head Home
Copyright 2026, Jack B. Siegel, All Rights Reserved. Do Not Alter, Copy, Display, Distribute, Download, Duplicate, or Reproduce Without the Prior Written Consent of the Copyright Holder.



