A Bend man was shot and killed by police late Tuesday outside Gates after reportedly robbing two Bend businesses and fleeing nearly 100 miles in a stolen car.

The alleged crime spree that ended in the death of Brad Tyler Masters, 27, began around 10:15 p.m. at the Dutch Bros location at 603 NE Third St., Bend Police said in a statement.

Employees told police that a man, believed to be Masters, walked up to one of the drive-thru windows displaying a handgun and demanding money. He then ran to the nearby Domino’s Pizza location at 253 SE Yew Lane where he also showed employees a handgun and demanded money, according to Bend Police Lt. Juli McConkey.

Masters allegedly stole a Domino’s employee’s car and left with an undisclosed amount of money from both businesses, McConkey said. Driving at high speeds, police say Masters first headed south on the Bend Parkway, then west on U.S. Highway 20 toward Sisters.

Bend officers radioed ahead to Oregon State Police and the Deschutes County Sheriff’s Office with information about the robbery and the stolen vehicle, McConkey said.

A Deschutes County sheriff’s deputy just past Tumalo reported seeing the stolen 2017 Hyundai Elantra travel past him at around 90 to 100 mph, McConkey said.

Several officers attempted to stop Masters, including one who backed off as they approached Sisters. Masters also avoided a set of spike strips laid by a Black Butte Police officer on the highway east of Sisters.

Deschutes deputies sent out a call to surrounding agencies to help locate Masters. He was spotted east of Santiam Pass on state Highway 22, and officers with OSP and the Linn and Marion county sheriff’s offices pursued him for stretches.

Masters was finally stopped by spike strips near Gates. According to police, he got out the Elantra and “a confrontation ensued.” Four officers fired shots and Masters was declared dead at the scene.

Preliminary information does not state whether Masters fired a shot or if he did anything that triggered the law enforcement officers to shoot him. No police were injured in the incident.

One Linn County sheriff’s deputy and three Oregon State Police officers were placed on leave as the Marion County District Attorney’s Office conducts a lethal force investigation. They are deputy Brandon Rathelegurche and troopers Caleb Yoder, Michael Iacob and Joseph Sousa.

Masters had extensive involvement in the Deschutes County justice system over the past three years — four separate cases in 2018, 11 in 2019 and eight this year. In May, he was sentenced to 10 days jail for breaking windows at Hobby Lobby and Kay Jewelers in Bend. He was on probation at the time of his death.