Since Sept. 1, right-wing street brawler Tusitala "Tiny" Toese has been held in the Multnomah County Jail for violating terms of his probation agreement. A fellow inmate has come to his defense, with a legal argument that echoes the complaints of Toese's ideological opponents.

In January 2020, Toese, a self-described Proud Boy, pleaded guilty to assault for punching a man on a North Portland sidewalk in 2018. As part of his plea agreement, the judge barred Toese from attending protests in Multnomah County for two years.

That didn't stop the 24-year-old from attending multiple protests this summer, including an Aug. 22 Proud Boys rally in downtown Portland. One week after the rally, Washington state officials arrested Toese on several probation violations. Since then, he's been held in the Multnomah County Jail in downtown Portland.

Now, a surprising character has come to his aid.

WHO: Benjamin Barber, 35. In 2016, jurors found him guilty of disseminating intimate images of a woman and uploading them to five different pornographic websites. Barber is currently being held in Washington County Jail following a probation violation.

WHEN: On Sept. 11, Barber filed a pro se motion in Toese's case, arguing that Toese's probation agreement is unconstitutional because barring him from attending protests acts as a prior restraint on Toese's constitutionally protected free speech. Barber claims he and Toese had previously attended a "free speech protest" together in 2017 and that he "intends to attend other protests with [Toese] in opposition to the Marxist and new Marxist philosophies."

THE ARGUMENT: Barber acknowledges in the motion that the probation agreement "was meant to prevent potential violence between the Defendant and the group Antifa." That said, he cites landmark First Amendment cases, including Near v. Minnesota (1931) and New York Times v. Sullivan (1964), which placed strict limits on the government's authority to stifle speech.

"Prior restraints 'must be couched in the narrowest terms that will accomplish the pinpointed objective permitted by constitutional mandate and the essential needs of public order,'" Barber says, citing a 1968 ruling. "Thus the order by the court amounts to a heckler's veto of speech, hoping that by freezing the defendants speech that Antifa will not engage in disorderly conduct." He argues that if the sentence wasn't legal, Toese can't be jailed for violating it.

WHY IT MATTERS: Toese is one of the figures most despised by Portland's leftist demonstrators. And Barber's argument displays that enmity—taking a gratuitous poke at anti-fascists for fighting with Toese.

But left-wing activists might want to listen—they, too, have been barred from protests as a condition of their release from jail. A ProPublica investigation in July revealed that federal prosecutors were prohibiting releasing protesters from jail on the condition that they stop protesting. After criticism that such a condition was unconstitutional, federal defenders and prosecutors agreed to end that court practice. On Oct. 5, a Portland standup comedian, Christian Burke, agreed not to attend counterprotests, potentially indefinitely, or be present within five blocks of the federal courthouse in downtown Portland, as a condition of their release from jail.

One obvious difference is that Toese pleaded guilty. "There are certainly constitutional concerns raised by a sentencing condition like the one you mention," says Steven Wilker, a Portland-based lawyer who specializes in constitutional law. "But any kind of sentence condition restricts liberty, including the liberty to do things that would otherwise be permissible… If a defendant agrees to a particular condition—particularly one, as here, that is related to the charges he faced—as a means of avoiding an otherwise appropriate jail term, it would seem more difficult to argue that such a condition would amount to an unconstitutional condition."

WHAT TOESE'S ATTORNEY SAYS: Public defender Dave Peters, who is representing Toese, says he doesn't plan to utilize Barber's argument.

"I read through it and I don't think it has any merit," Peters said, adding that Toese wasn't aware Barber was filing the motion on his behalf. "He has nothing to do with that and neither do I. Mr. Toese says he doesn't know anything about it."

WHAT HAPPENS NEXT: Toese's next scheduled hearing is Tuesday, Oct. 20. The Multnomah County Department of Community Justice is calling for Toese to serve one year in jail.