A local real estate agent whose attempted murder charges made headlines in 2014 is now facing rape allegations from his most recent girlfriend.

Theodore Holland “Ted” Settlemier, 50, has been held without bail in Deschutes County jail since his arrest in late May. He’s worked as a real estate broker in Oregon for nearly 30 years and has an active license, according to Oregon Real Estate Agency database.

He is scheduled to enter a plea Wednesday on numerous charges including first-degree rape.

He was charged with attempted murder in 2014 after his then-girlfriend told police he’d held a pillow over her head for two minutes while telling her he was going to kill her, according to news reports. He pleaded no contest to fourth-degree assault in exchange for dropping the attempted murder charge and other charges. The state also agreed to drop one charge of stalking.

Court documents released this week detail law enforcement’s current case against Settlemier and describe an abusive relationship similar in several ways to the previous case.

On April 15, a woman called Bend Police to report that an argument with Settlemier had turned into an attack in which he kneed her in the sternum and threw her to the ground. Further interviews with the woman yielded multiple charges alleging sexual violence.

Officers with Bend Police were dispatched to a domestic dispute at a home in the Mountain View neighborhood, where Settlemier’s girlfriend lived with a roommate. He had reportedly left in his vehicle just before police arrived.

The girlfriend told officer Peter Enna she and Settlemier had been dating about a year and a half, though at the time of the incident, they’d been “breaking up” for about a month.

That night, they’d gone to the laundromat adjoining the M&J Tavern in Bend because their dryer was broken. Settlemier allegedly became “super intoxicated” at the tavern and before being cut off by his waitress, was heard yelling “all women are the devil.”

The couple retrieved their laundry, and Settlemier insisted on driving home rather than hailing a ride or letting his girlfriend drive his car, she said. He continued verbally abusing her while driving her home “like a psycho,” the woman told police.

Back home, Settlemier backed his girlfriend into a corner and “in a rage,” slammed a door into her three times, she told police. She curled into a ball to protect herself, but Settlemier allegedly opened her arms and kneed her in her sternum, causing her to fling her head backward into a wall.

In follow-up interviews, the woman told police that in September, Settlemier attacked her, sodomizing her with a sex toy as she tried to claw across the floor to get away from him.

She described instances of Settlemier turning violent during sex, including once when he allegedly threw the woman to the ground causing her to lose consciousness.

“(The woman) described the sexual attacks from Theodore becoming increasingly aggressive the longer they dated,” wrote officer Enna. “(She) described emotional abuse starting shortly after they started dating and increasing in intensity, to include physical and sexual abuse, during the course of their relationship.”

Settlemier has a history of violence against women, according to court records. Those cases list three other women as victims.

As part of his investigation in the current case, Enna called the victim in Settlemier’s 2014 attempted murder case. She was able to describe several scenarios and items Settlemier allegedly used in the current case without the officer telling her the details, Enna wrote in court documents.

The alleged victim in the current case said Settlemier was “obsessed” with recording their sexual encounters and that instances of violence and verbal abuse were likely still contained on his phone. This month, police applied for and received permission to search Settlemier’s phone, as well as his house on Fresno Avenue and his 2003 Mercedes-Benz ML 350.

He’s charged with first-degree rape, first-degree sodomy, two counts of menacing, two counts of first-degree unlawful sexual penetration, two counts of fourth-degree assault witnessed by a minor and three counts of second-degree sexual abuse.

His attorney, Todd Grover, did not return a call seeking comment.

— Reporter: 541-383-0325, gandrews@bendbulletin.com