He Heckled a District Attorney on TV. Now He Faces 10 Years Behind Bars.

On Wednesday, a Massachusetts judge will decide whether Joao DePina will face the possibility of a decade behind bars for publicly criticizing a district attorney.

On Wednesday morning, Joao DePina will walk into a Massachusetts courthouse to learn whether he could face the possibility of spending a decade behind bars.

His alleged crime? Heckling a district attorney from afar during a live press conference.

DePina repeatedly interrupted then-Suffolk County D.A. Rachael Rollins during a November press conference to criticize Rollins' professional and personal behavior. His shouts were picked up on local news broadcasts, and Rollins paused on several occasions to ask DePina to stop interrupting her attempt to give an update on two cops who had been shot earlier that day. DePina also livestreamed his tirade, during which he criticized Rollins' nomination to be a U.S. attorney (she was confirmed to the post in December, becoming the first black woman to be U.S. attorney for Massachusetts).

While DePina's behavior during the press conference was clearly uncivil and rude, prosecutors say it's also criminal. DePina was charged in November with one count of witness intimidation in connection to his antics at Rollins' press conference. He could face between 2.5 and 10 years in prison if convicted.

"This is the most grossly unconstitutional thing I have seen in my entire career," Marc Randazza, a free speech attorney who is representing DePina, tells Reason. "If the First Amendment means anything, Joao walks free."

In court documents, Randazza describes DePina's arrest and subsequent charges as "censorious and unconstitutional," and asks for the charge to be dropped. A hearing was held in March on the motion to dismiss the charge, and District Judge Carol Ann Fraser is due to announce her decision on that matter Wednesday. If she rules against DePina, the case will proceed to trial.

Meanwhile, prosecutors alleged in court documents that DePina ran afoul of Massachusetts law by criticizing Rollins at the same time that he was the defendant in "three separate and open cases pending in District Court which were being prosecuted by the Suffolk County District Attorney's Office," which Rollins ran at the time. His tirade was an attempt to influence her handling of those cases, prosecutors argue, making his speech "neither lawful nor protected."

But that argument seems to ignore the substance of DePina's November tirade aimed at Rollins. Though he veered from political to personal attacks and back again on several occasions, DePina never referenced the legal proceedings and never threatened Rollins.

"Mr. DePina made no threats. Mr. DePina engaged in no form of harassment, nor anything that could possibly be construed as intimidation of someone connected to a pending criminal proceeding," Randazza argues in court documents. "Rather, Mr. DePina exercised his right to criticize a District Attorney for abusing her power, opportunistically seeking higher office without caring for the people of Boston, and not taking adequate care of Boston police officers."

The case, he argues, is Rollins' attempt to "abusively use the power of the state to swat down a political opponent."

As Reason's Billy Binion noted recently in connection to another case where someone was arrested for criticizing law enforcement, the Supreme Court has held that the First Amendment protects "the freedom of individuals verbally to oppose or challenge police action without thereby risking arrest," calling that right one of the chief distinctions separating "a free nation from a police state."

Adding to this case's weirdness is the fact that DePina appeared to have volunteered for Rollins' successful 2018 campaign to become district attorney, according to photos unearthed by a local political blog, TB Daily News. The same blog notes that DePina has pulled the same antics at other high-profile press conferences in recent years. He also ran unsuccessfully for Boston City Council in 2017.

DePina seems to be a troll. That's no reason to throw a man in jail for a decade—or at all.