Crooked River Ranch man arrested in Halloween holdup at gunpoint of Redmond cafe
(Update: Suspect arraigned, judge sets bail at $515,000)
REDMOND, Ore. (KTVZ) -- A suspect in the Halloween night holdup at gunpoint of Sassy's Cafe in Redmond has been arrested at his home in Crooked River Ranch, police said Tuesday.
Lt. April Huey said Douglas Richard York, 54, was arrested around 3 p.m. Monday by members of the Central Oregon Emergency Response Team (CERT).
"The arrest was made in connection with the robbery as well as for an outstanding warrant on an unrelated matter," Huey said.
York was booked into the Deschutes County Jail in Bend on eight felony charges - first-degree robbery, first-degree theft, unlawful use of a weapon, three drug (fentanyl) possession and delivery charges and felon in possession of a firearm, along with a misdemeanor count of menacing.
Court records show York has a criminal history dating back to 1991. Most recently, he was charged in mid-October with a second-degree theft on July 13 of items worth $100 or more from the Redmond Walmart, and also charged with a theft of merchandise worth $1,000 or more from the same store 11 days later. A $10,000 warrant for York's arrest was issued on October 31, just hours before the Redmond robbery.
York appeared by video from jail for Tuesday's arraignment. Circuit Judge Alycia Sykora set York's bail at over $500,000, as prosecutors requested, and set several conditions, including no contact with the victimized businesses, no illegal drugs or weapons and not to leave the state. He's due back in court Dec. 16 for arraignment on an expected grand jury indictment.
Huey said, "RPD would like to thank the Redmond and Crooked River Ranch communities for their assistance during this investigation. RPD would also like to thank the Oregon State Police Crime Lab, CERT, Bend Police Department, Deschutes County Sheriff’s Office, and Jefferson County Sheriff’s Office for their assistance in the investigation of this incident."
Earlier story:
REDMOND, Ore. (KTVZ- November 2, 2025) KTVZ News has obtained exclusive security video of a masked gunman who robbed Sassy's Cafe in downtown Redmond on Halloween night. We also spoke with a manager about the confrontation.
Officers responded shortly before 5 p.m. Friday to the report of an armed robbery at the NW Fifth Street restaurant, Lieutenant April Huey said earlier Monday in a news release, accompanied by a photo taken from the security video.
"The male suspect entered the cafe, displayed a black handgun and demanded money," Huey said in a news release.
"The suspect left the business on foot and has yet to be identified," she added.
No employees or customers were injured in the incident, according to police.
In the video obtained by KTVZ, you can see the suspect enter the cafe, flash a handgun in his waistband at a worker and demand money.
Night shift Manager Joe Costello told us: "He told me that he had 'had a bad day.' He threw a Crown Royal bag on the counter and, um, showed me his gun. It was underneath his, in his waistband.
The suspect was wearing a black ski mask, black hat and black pullover with an Adidas logo, along with blue jeans and Romeo-style boots, Huey said.
"Police are asking the public if anyone witnessed the incident or saw the suspect at Sassy's on Friday at 4:50 a.m. to contact RPD," Huey said. Anyone with information about the case is asked to contact Redmond Police through the non-emergency dispatch number, 541-693-6911.
Earlier story:
REDMOND, Ore. (KTVZ) - KTVZ has received multiple reports that Sassy’s, the cafe located inside the Cruise N Market and Deli in Redmond, was robbed this week.
Details on the incident remain limited. KTVZ has reached out to Sassy’s for comment, but staff have declined to speak at this time.
Redmond Police confirmed they were aware of the situation and said an official statement would be released. As of Sunday evening, that statement has not yet been issued.
This is a developing story. We will provide updates as more information becomes available.
