A Portland man with a history of harassing law enforcement and court officials pleaded guilty Tuesday to assaulting a federal officer.

The judge almost didn't accept the plea as Cyrus Andrew Sullivan, 35, denied the prosecution's allegation that he had elbowed Multnomah County sheriff's Deputy Tim Baker in the face and neck while in custody on a federal hold on June 28, 2017.

Cyrus Sullivan

Sullivan said he "didn't throw an elbow,'' but "nailed him right in the face'' with spicy chips he had been eating.

In a struggle that ensued, Sullivan suffered a broken arm but the deputy wasn't hurt, he argued.

Sullivan had run back to his cell on the second tier in the downtown Portland jail after learning that the deputies planned to return him to solitary confinement in "the hole.'' He closed the door behind him. When deputies couldn't convince Sullivan to put his hands through the small food portal of the cell door to be handcuffed, they opened the cell door.

Prosecutors still maintained he threw an elbow but also noted that Sullivan threw crushed Sriracha Dorito chips at the deputy, "using the spicy dust as a weapon, like pepper spray,'' according to a court document.

"I reacted in a way I regret now so I'm taking responsibility,'' Sullivan said, but continued to deny throwing an elbow. He suggested the deputy may have struck his elbow when he ran into the cell.

After brief huddles with his lawyers and the prosecutor, Sullivan clarified, "I struck him with chips. I assumed a threatening stance when he came in.''

Sullivan's lawyer Tiffany Harris says Sullivan threw chips, alternately described as "flaming hot tortilla chips,'' "scorching chips,'' or "super spicy chips,'' that are part of a special line of products exclusively sold in the jail commissary.

"Our investigation revealed that snack chips are often crushed up and used as a seasoning for the bland food on the jail's menu, though Mr. Sullivan denies the claim that the chips in question were crushed or turned into a weaponized powder,'' Harris said.

While prosecutors contend Sullivan caused physical injury to the deputy, Sullivan and his lawyers said law enforcement officials documented no injuries. The deputy didn't receive medical treatment or time off as a result of the encounter, Sullivan's lawyers argued.

In contrast, Sullivan suffered a fracture to his left humerus bone, between his elbow and shoulder, in the struggle with deputies that followed.

Sullivan is expected to be sentenced Nov. 28 to time served, followed by three years of supervised release. Under the plea deal, he will waive his right to appeal the sentence. Prosecutors also will dismiss an indictment that charged him with five counts of impeding a federal officer.

He's already served two years for threatening a woman in a dispute over his controversial stdcarriers.com website and extra time for violating his supervised release by creating a controversial website called copblaster that posted biographies and complaints against law enforcement officers, correctional guards and judges.

A federal judge in Arizona, U.S. District Judge Jennifer G. Zipps, was brought in to handle Sullivan's assault case after Sullivan sent an intimidating letter to the home of Oregon's U.S. District Judge Marco A. Hernandez while in custody.

In the letter, Sullivan said he was handing out Hernandez's home address to other inmates like Halloween candy. In April, Hernandez delivered a severe rebuke to Sullivan, calling his letter a "disgusting, offensive and perhaps illegal'' way to influence the criminal justice system. Hernandez then recused himself from the case.

Sullivan's diagnosis of Asperger's disorder created "unique challenges'' in the jail environment, his defense lawyer wrote to the court.

"Mr. Sullivan has not had any mental health treatment since he was ordered detained last September and the absence of mental health services has exacerbated his symptoms and taken a toll on his overall functioning,'' Harris wrote.

-- Maxine Bernstein

mbernstein@oregonian.com

503-221-8212

@maxoregonian