On a Sunday morning in May 2019, a Columbia County sheriff’s deputy pulled up behind Dillon Shane Webb’s Chevrolet truck at a stoplight and didn’t like what he saw on the rear window. What followed became one of the most talked-about First Amendment showdowns in recent Florida history.
Webb, a 23-year-old Lake City resident, was driving along U.S. Highway 90 when Deputy Travis English spotted his “I EAT A**” bumper sticker. The deputy concluded the sticker violated Florida’s obscenity law. First Coast News He pulled Webb over and told him to remove it.
Webb said no.

“I’m Buckled, I’m Not Speeding — What’s the Issue?”
“I saw the cop at the courthouse and he whipped around to follow me,” Webb later said. “I thought to myself, I’m buckled, I’m not speeding, all my lights work, what’s the issue? He said, ‘Hey man, don’t you think that sticker is pretty vulgar?'” First Coast News
Webb stood his ground. He cited his First Amendment right to free speech and refused to alter the sticker on the spot.
After Webb refused to remove part of the sticker to censor the word, the deputy arrested him and charged him with “obscene writing on vehicles and resisting an officer without violence.” Reason Magazine His vehicle was searched and towed.
Deputy English had contacted his supervisor before making the arrest. Wakeforestlawreview Both signed off on taking Webb to jail over a bumper sticker.

Four Days Later, the Case Fell Apart
In a May 9 letter to the Columbia County Sheriff’s Office, Assistant State Attorney John Foster Durrett stated that all charges against Webb had been dropped, and that his sticker was in fact protected by the First Amendment. Orlando Weekly
“Having evaluated the evidence through the prism of Supreme Court precedent, it is determined the Defendant has a valid defense to be raised under the First Amendment,” Durrett wrote. “A jury would not convict under these facts.” Orlando Weekly
The State Attorney applied the Miller v. California legal test — the Supreme Court’s standard for defining obscenity — and determined the sticker did not meet it. First Coast News
Webb came from a military family. He said that since veterans fought for his First Amendment rights, he was going to keep the sticker on his truck. First Coast News Notably, the deputy who arrested him was also a veteran.

Webb Sued. Then Came the Twist.
Webb filed a federal civil rights lawsuit — Webb v. English — arguing his First and Fourth Amendment rights had both been violated.
In September 2021, U.S. District Judge Marcia Morales Howard issued a ruling that stunned many legal observers. She ruled that the arrest was “arguably justified under Florida’s obscenity law,” granting the officer and his supervisor qualified immunity from the lawsuit. ABA Journal
The judge wrote that “if the sticker depicted a sexual act, it would be protected speech under the First Amendment only if it had serious literary, artistic, political, or scientific value.” Reason Magazine
In other words — the cop couldn’t be sued because the law, though later found inapplicable, wasn’t clearly unconstitutional at the moment of the arrest. That legal shield is called qualified immunity, and it has protected officers from accountability in courts across the country.
Eugene Volokh, a constitutional law professor at UCLA, said he believes the decision was wrong. “Obscenity is limited to ‘hard-core pornography,’ and it’s hard for me to see how a short vulgar description of sex would qualify,” he wrote. ABA Journal
There was one partial win for Webb. The judge allowed his Fourth Amendment claim — that the search and impoundment of his vehicle after the arrest was unlawful — to move forward. ABA Journal

What We Know

May 5, 2019: Webb pulled over on U.S. Highway 90 in Columbia County, Florida
Charge: “Obscene writing on vehicles” under Florida Statute 847.011 and resisting an officer
May 9, 2019: State Attorney drops all charges — First Amendment defense deemed valid
Webb files suit: Webb v. English, alleging civil rights violations
September 2021: Federal judge grants qualified immunity to the arresting deputy and his supervisor
Fourth Amendment claim: Allowed to proceed — the vehicle search and impound remained legally contested
Expert opinion: Constitutional law professor Eugene Volokh publicly argued the qualified immunity ruling was incorrect

Why This Case Reaches Beyond One Sticker
This story isn’t really about a bumper sticker. It’s about who gets to decide what Americans are allowed to say in public — and what happens when law enforcement makes that call incorrectly.
The charges were dropped. The law sided with Webb. But the officer who put him in handcuffs faced no legal consequences. That outcome — charges dismissed, qualified immunity granted — is playing out in courtrooms across the country, and it raises a question millions of Americans are already asking: If your rights were violated, but the violation wasn’t illegal at the time, did your rights actually matter?
Webb’s attorney put it plainly after the charges were dropped: “Now we transition from defense to offense. The First Amendment was our defense. What is Sheriff Hunter’s defense?” First Coast News
In a free society, the Constitution protects speech precisely because the government cannot be trusted to approve only the speech it likes. Webb’s case proved the system can eventually course-correct — but “eventually” came with a tow bill, a night in custody, and years of litigation.
The sticker stayed on the truck.