When Free Speech Depends on Who's Burning What
A decade ago, stories started circulating about department stores installing "skinny mirrors.” These dressing room mirrors subtly angled or distorted to make customers look slimmer, in hopes they'd feel good enough to buy the clothes. The reaction split in an interesting way. Some people were outraged and called for investigations. Others bought the same mirrors for their own homes.
I want to define a version of that mirror precisely, because I'll use it throughout this piece: a system in which identical expressive acts are evaluated differently depending on political alignment, whether through public rhetoric or through how a law actually gets enforced. Not "everything I disagree with." Specifically that: the same act, judged on different terms, depending on who's doing it and who's watching.
In 2024, I wrote about then-candidate Trump reviving his call for jail time for flag burning, and I wrote it as a warning. I'm updating that piece now because the warning is no longer hypothetical, and because the record since gives us something to actually examine rather than predict.
What happened
In August 2025, President Trump signed an executive order titled "Prosecuting Burning of the American Flag." The order directed the Justice Department to prioritize enforcement of flag desecration cases "to the fullest extent permissible under any available authority." Its stated legal theory is narrower than the political rhetoric surrounding it: it argues that while Texas v. Johnson (1989) protects flag burning generally, the Supreme Court has never held that flag desecration "likely to incite imminent lawless action," or that amounts to "fighting words," is constitutionally protected and it instructs prosecutors to pursue cases under that theory, or under unrelated content-neutral laws such as property destruction or local fire ordinances, wherever applicable.
Trump followed the order with a social media post stating that anyone burning the flag would be "immediately arrested" and would face one year in prison, "no early exits, no nothing." The same day the order was signed, a combat veteran named Jan Carey burned a flag outside the White House in protest of it and was arrested under a public park fire ordinance. Seven months later, prosecutors dropped the case after a federal judge ruled Carey was entitled to further inquiry into whether the administration was vindictively prosecuting him.
Between 2015 and 2025, Trump's public position on flag burning shifted from acceptance to criminal condemnation, even though the underlying constitutional doctrine did not change. In a 2015 interview with David Letterman, recorded months before he launched his presidential campaign, Letterman raised flag burning as an example of free expression: "If that's how you feel, go ahead and burn the flag. Because this country is far greater than that symbol, and that symbol is standing for freedom of expression." Trump's response, on the record: "Sure. You're 100 percent right. I understand where you're coming from. It's terrific."
Vice President Vance's record runs on a similar two-track timeline. At the 2024 Republican National Convention, accepting the nomination for vice president, Vance said the party of the next four years would be "united in our love for this country, and committed to free speech and the open exchange of ideas." In February 2025, he delivered a widely covered address at the Munich Security Conference arguing that free speech was "in retreat" across Europe, citing Sweden's prosecution of a man for Quran burning as a specific example of governments wrongly treating provocative symbolic expression as criminal conduct. Six months later, when Trump signed the flag order, Vance went further than the order itself, posting that Texas v. Johnson (the precedent protecting flag burning) was wrongly decided, and that Chief Justice Rehnquist's dissent, not Justice Scalia's majority vote, had been correct.
What it suggests
None of the facts above, on their own, prove that the enforcement strategy is unconstitutional. Courts have long allowed governments to apply content-neutral laws like fire codes, vandalism statutes, and disorderly conduct ordinances to conduct that happens to be expressive, under the framework set out in United States v. O'Brien (1968), which permits incidental restrictions on speech when a law serves a substantial government interest unrelated to suppressing the message itself. Selective enforcement and vindictive prosecution claims are also difficult to win in court; they require evidence of intent and pattern, not just an unfavorable outcome in one case.
So the strongest version of the argument here isn't "this is illegal because flag burning is protected speech." It's narrower and harder to wave away: this becomes constitutionally suspect to the extent enforcement is selectively aimed at a disfavored message rather than genuinely neutral conduct. That a federal judge found Carey entitled to inquire into vindictive prosecution is meaningful precisely because it's a court, not just a critic, recognizing that the pretext question is live. First Amendment doctrine has long been sensitive to that exact pattern: a facially neutral law applied in a way that consistently tracks the viewpoint being expressed, rather than the conduct itself.
The Trump-Letterman and Vance-Munich material doesn't prove a legal violation either. What it suggests is something narrower but still worth naming: a public position on flag burning, and on symbolic protest generally, that tracks whose protest it is and what it's protesting, more reliably than it tracks any stable First Amendment principle. Burning a Quran in Sweden was described, in detail, as a violation of conscience and expression worth international attention. Burning a flag in Washington became the occasion for revisiting a 36-year-old precedent. The mirror, as I defined it above, is the consistent thing here — not any one statement or prosecution, but the pattern across both.
I understand this instinct better than most people, because I've lived inside a version of it myself. The USPTO denied my band's trademark application, labeling our name "disparaging," even though survey evidence showed an overwhelming number of Asian Americans found The Slants empowering rather than offensive. The agency wasn't measuring documented harm. It was measuring its own discomfort and calling that harm, a content-based judgment dressed up as a neutral administrative standard. In 2017, the Supreme Court unanimously rejected that reasoning, holding that the government cannot use a registration system to filter expression based on viewpoint.
The structural question is the same one running through the flag cases: when a facially neutral process (a registration standard, a fire ordinance, a "fighting words" carve-out) gets applied in a way that consistently lands on disfavored expression and consistently spares favored expression, the neutrality is doing less work than it claims to. That's not a question with a single legal answer that resolves every case. It's a pattern worth tracking carefully, case by case, rather than assuming away in either direction.
A U.S. flag is a piece of Chinese-made fabric that is replaceable for twenty-five dollars. A legal and political culture willing to track its own stated free-speech commitments only when they're convenient is much harder to repair once the habit sets in. Insulating a democracy against that kind of selective erosion requires the harder work of applying the same standard to speech you find admirable and speech you find repulsive… and being honest about the mirror, especially in the moments when it happens to be flattering you.
I speak on First Amendment law, civil liberties, and the gap between stated principle and selective enforcement at law schools, bar associations, and civic organizations. If these questions connect to work you're doing, simontam.org/speaking is the place to start.
