‘Trump Car’ owner rejects settlement as legal battle with city turns into free speech showdown

One Long Island man’s rolling political statement has turned into a full-blown legal battle, and he’s not backing down — even with money on the table. Michael Wasserman, known locally for driving vehicles covered in pro-Trump flags and messages, is refusing to settle with the city of Long Beach after officials tried to force him to remove the displays.

What started as a neighborhood dispute has turned into a broader fight over free speech, government authority, and how far local ordinances can go to dictate what drivers keep in their vehicles.

A car collection that sparked a legal battle

Wasserman’s vehicles — including the Porsche Carrera, Jeep Wrangler and Humvee — aren’t subtle. Each is covered with bold political messages and flags, some of which contain explicit language aimed at current political figures. Cars quickly made him a recognizable figure around Long Beach, drawing both support and feedback from residents.

In 2021, city officials entered a local ordinance prohibiting certain types of demonstrations within city limits, citing local ordinances. They ordered Wasserman to remove the flags, arguing that his vehicles violated those rules.

Wasserman saw it differently. He argued the order crossed a constitutional line and filed a $25 million lawsuit in federal court against the city, its police leadership and other officials. From his perspective, the issue wasn’t about signage—it was about whether the government could dictate individual expression on private property.

A settlement was offered – and rejected

After years of legal back-and-forth, Long Beach officials tried to put the case to rest. In February, the City Council approved a $50,000 settlement to settle the dispute.

For most people, that would be the end of the story. For Wasserman, it wasn’t even close.

He rejected the offer outright, insisting the amount was less than the lawsuit represented. He’s now holding out for at least $100,000, framing the fight as a matter of principle rather than profit. According to him, the goal is to protect the basic rights and not in cash.

Tension off the court

The conflict is not limited to the legal realm. Wasserman claims he has been the target of frequent complaints from neighbors, prompting frequent police visits to his home. He also accused them of damaging the tires and windows of their vehicles and vandalizing them.

While those claims have not been confirmed by authorities, they highlight the severity of the situation. The local ordinance issue has clearly struck a nerve in the community, dividing residents and seemingly raising tensions beyond city hall.

At the same time, Wasserman says he’s received quiet support from others in the area who appreciate his willingness to push back against the city.

Why it matters to drivers

This case goes beyond a man and his car. This raises big questions about what drivers are allowed to display in their vehicles and where municipalities draw the line between regulation and prohibition.

For car enthusiasts, the implications are hard to ignore. Vehicles have long been a form of personal expression, whether through decals, wraps, or custom builds. If local governments could regulate messages in cars under sweeping ordinances, that could open the door to broader restrictions that would have far more impact than political demonstrations.

There is also the issue of selective enforcement. These types of situations often raise concerns that the rules are applied unevenly, depending on the message that is being displayed rather than the action.

big picture

At its core, this controversy sits at the intersection of free speech, local governance, and car culture. It highlights how quickly personal expression can become a legal flashpoint when it clashes with community norms or political sensitivities.

It also underscores the growing tension in cities across the country, where regulations aimed at maintaining order can collide with individual rights — especially when those rights are exercised loudly and publicly.

As the case drags on, one thing is clear: It’s not just about the flag on the car. How much control governments should have over what drivers do with their vehicles — and whether pushing back comes with a price.

The real question now is whether this fight ends with a big payoff, or sets a precedent that can reshape how far cities can go in telling cities what they can and can’t perform.