Theodore “Ted” Settlemier II

Theodore Holland “Ted” Settlemier II, a once-successful Bend real estate agent, was sentenced to 14 months in prison for strangling and assaulting a girlfriend in 2019. But having already served time in jail after his arrest, the question at his sentencing Tuesday in Deschutes County Circuit Court was whether he’d have to travel to Wilsonville to be entered into the state prison system.

It was not Settlemier’s first time in court for abusing a girlfriend. In a separate case in 2014, Settlemier was accused of attempted murder for holding a pillow over a girlfriend’s face and threatening to kill her. He ultimately pleaded no contest to fourth-degree assault, strangulation and coercion and was sentenced to 30 days in jail, three years probation and restitution of $1,747.

Settlemier’s recent case originated in April 2019 when a woman told police he’d attacked her during an argument. She also alleged that Settlemier sexually abused her, though all allegations of sexual violence were ultimately dropped from his indictment.

While awaiting trial, Settlemier was incarcerated in the Deschutes County jail four different times for violating his release conditions. One span in custody, from Jan. 26, 2020, to March 5, 2021, lasted 404 days. At one point, in 2020, he tampered with his ankle monitor and left house arrest. Police sought the public’s help bringing him in.

Earlier this month, following a two-day trial at the Deschutes County fairgrounds, Settlemier was found guilty of misdemeanor strangulation and the felony of fourth-degree assault witnessed by a child.

At Tuesday’s sentencing, Deschutes County Judge Ray Crutchley heard arguments from the prosecution and defense as to whether or not Settlemier should be transported to Coffee Creek Correctional Facility in Wilsonville to be “booked and printed” and entered into the state prison system.

Prosecutor Michael Swart of the Deschutes County District Attorney’s Office said at Coffee Creek, state officials could “properly” calculate Settlemier’s time behind bars.

“The very process of him going through the processing center and having them do the calculations would be much more appropriate in this case because, it really seems to me, in my humble opinion, that Mr. Settlemier doesn’t understand the serious nature of what he’s done,” Swart said.

Swart noted Settlemier’s history of abusive behavior, dozens of instances of violating restraining orders and the escalating severity of his crimes.

“Unfortunately, Mr. Settlemier is a person who doesn’t really abide by laws or take court orders very seriously, particularly when it comes to his relationships with women,” Swart told the court.

Settlemier’s court-appointed attorney, Shawn Kollie, argued a transport to Coffee Creek, “makes no sense and is entirely and unnecessarily punitive,” noting his client’s reputation has already suffered as a result of the case.

“Mr. Settlemier is not a man of much means at the moment,” Kollie said. “His future in real estate is extremely hampered by this felony conviction.”

Crutchley asked if there was any disagreement that Settlemier had served 14 months in custody, and heard none. He then ruled against the state’s request to send Settlemier to prison, albeit for a few days.

“He has served his time. The court isn’t going to do something to merely inconvenience him. I don’t get that,” Crutchley said.

The judge furthered ordered Settlemier serve two years post-prison supervision, avoid bars and liquor stores and attend a batterers intervention class.

“At this point, I don’t have anything to say,” Settlemier said when given a chance to address the court.

Prosecutors sought a $2,000 conviction fee, which is $1,800 higher than the standard fine for Settlemier’s offenses.

Crutchley waived the fee altogether, which he often does for defendants.