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A large American flag draped across the front of the New York Stock Exchange Aug. 5, 2011.STAN HONDA

Robert Bell doesn't like the police. So when the aspiring lawyer spotted three officers in New York's Greenwich Village, he extended his middle finger to their backs.

Little did he know his actions would spark a legal battle over free speech and the right to flip off the cops.

Mr. Bell didn't realize he'd be spotted by another officer nearby. And the fourth officer didn't take it well, allegedly approaching him with the question: "Do you think that's funny?"

According to a suit filed this month, Mr. Bell was cuffed before he could respond. He alleges he was not read his rights before being questioned and was taken to a holding cell, where he was taunted with homophobic insults by police.

The charge was dismissed when the arresting officer failed to show in court. Mr. Bell decided that was not good enough and chose to sue. He insists the officers interfered with "activity protected by the First Amendment," and thus he was taken into custody on bogus grounds.

The New York Police Department has not responded to a request for comment.

Mr. Bell joins a colourful U.S. tradition of testing and expanding the boundaries of free speech. Books once seen as transgressive are now published freely and the flag can be burned without legal punishment. And there have been a number of cases establishing that giving the finger, on its own, is not illegal.

In one such case – that of an Arizona man stopped after gesturing obscenely and shouting profanities at a police officer – Court of Appeals judges called Ralph Duran's conduct "boorish, crass and, initially at least, unjustified" and argued that police "surely" deserve better treatment.

"But disgraceful as Duran's behavior may have been, it was not illegal; criticism of the police is not a crime," the judges wrote. "Inarticulate and crude as Duran's conduct may have been ... it fell squarely within the protective umbrella of the First Amendment and any action to punish or deter such speech – such as stopping or hassling the speaker – is categorically prohibited by the Constitution."

Another case, this one in Massachusetts, concerned a man who had a beef with a particular police officer and repeatedly gave him the finger. The ruling there acknowledged the free speech argument while noting that there were still restrictions.

"Like its verbal counterpart, when it is used to express contempt, anger, or protest, it is a form of expression protected by the First Amendment," wrote Judge Ralph Gants, of the state's Supreme Judicial Court. "But in certain limited circumstances, when accompanied by other less expressive and more threatening conduct, raising the middle finger may constitute fighting words or a true threat."

Mr. Bell's suit says that the arresting officer exaggerated the situation to make it seem that he had caused "public alarm and annoyance" in a "large crowd." In fact, he alleges, there were no more than three bystanders and they did not appear to notice his action.

In the suit, Mr. Bell claims a litany of abuses of his rights against retaliatory arrest and prosecution, unreasonable seizure and abuse of process. All of these stem from his contention that the police had no right to arrest him in the first place. He also alleges widespread misconduct and abusive practices within the New York Police Department.

"As a result of the defendants' conduct, Mr. Bell legitimately fears he will be unable to gain admission to the law school(s) of his choice since the preferred schools require the applicant to disclose the facts underlying any arrest," the suit alleges.

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