Wild West Lives On

90-Year-Old Umatilla County Deputy Is One Of Nation's Oldest, Also A Veteran of the Korean War

By Jessica Pollard, Hermiston Herald. Reprinted with permission.

The year was 1985. Morrow County Sheriff Roy Drago spotted a white 1966 Plymouth— reportedly stocked with thousands of dollars’ worth of stolen Eastern Oregon Bank receipts—heading north on Ella Road.

Drago went in for a high-speed chase, and fired a shot at the vehicle, according to a historical account published by the Oregon Sheriff ’s Association.

“Rural Oregon then was quite different than rural Oregon today. It was more like the old west days,” Drago said.

The chase eventually culminated in the arrest of two escaped prison inmates, including John William Krebs, grandson of the bank’s founder. Just two years prior, Krebs pleaded guilty to charges surrounding a robbery of the same bank according to the Heppner Gazette-Times. Drago was there for that too.

And while Drago retired from his four-term reign as Morrow County Sheriff in 1999, he’s still a staple in the Eastern Oregon law enforcement community.

He celebrated his 90th birthday at the Stafford Hansell Government Center on a Friday afternoon in December 2019 and went back to work the following Monday as a court security deputy for the Umatilla County Sheriff ’s Office in Hermiston.

“He’s one of the oldest active deputies in the U.S.,” Sheriff Terry Rowan said. “He’s had quite the career.”

Of course, life is slightly mellower now.

“I don’t do a whole lot anymore,” Drago said.

When he’s not working, he enjoys fishing with his son who lives in Boardman and seeing his grandchildren. He used to hunt but gave up the sport almost three decades ago.

And after a law enforcement career spanning almost 50 years, he’s grappling with the modern era of policing.

“My observations are that the pendulum has swung so far to the left in terms of laws and how criminals are treated. We seem to have lost our perspective on punishment,” he said. “I wouldn’t recommend a law enforcement career for anybody today. That’s not to say we don’t need people.”

Drago explained that, although he’s retired twice, he picked up work with the Umatilla County Sheriff ’s Office again to offset retirement savings lost in the stock market. But he also appreciates the sense of community he’s collected over the years.

“I’ve made an awful lot of friends here,” he said. “There are so many people that I know. It’s a pleasure being here.”

Those who listen closely can still hear an East Coast lilt in Drago’s voice. It’s one of the last remaining clues that he was born in Yonkers, New York in 1929.

Upon graduating high school, he came to live and work with his uncle in Oregon until being drafted into the U.S Army during the Cold War.

“I think that set a standard for me to follow the rest of my life,” Drago said. “To be at work on time, to maintain a good relationship with my employer and employees. And I still make my bed every day.”

After being discharged from the military in 1954, Drago landed a job with the Yonkers Police Department, as a patrolman assigned to animal control. But following what he describes as a “nasty” divorce, Drago decided to head back to the west.

“I wasn’t a stranger,” he said.

Drago eventually found himself working for the Eastside Police Department in Coos Bay. When the department merged with the Coos Bay Police Department in 1980, he shipped over to Morrow County and started working for the sheriff ’s office.

In 1983, he was appointed sheriff, and it was the beginning of the most challenging part of his career.

“I got appointed to that job not knowing anything about what a sheriff is supposed to do. I knew what a police officer was supposed to do, but not a sheriff,” Drago said. “It’s a political role.”

He retired in 1999 during his fourth term. Then a few years later, Drago took a job with the Umatilla County Sheriff ’s Office. He retired there in 2012, but now he’s back.

Drago celebrated 18 years with the Umatilla County Sheriff ’s office in January.

The heartbreaks, mishaps, and adventures that pair with his lengthy career are immortalized in a poem written by his co-worker, deputy Tim Gallaher, aptly dubbed “The Ballad of Roy Drago.”

“You’d think his job is done,” it reads. “But Roy still wears a shiny badge and buckles on his gun.”

Umatilla County Sheriff’s Deputy Roy Drago, 90, cuts his birthday cake as Sheriff Terry Rowan watches on a party for Drago in December.

Photo by Ben Lonergan, Hermiston Herald

Sheriff Drago on Patrol

By Tim Dees

This is a portion of an article that originally appeared on PoliceOne.com, the online resource for Law Enforcement, and is reprinted by permission of the PoliceOne editorial team. Visit PoliceOne to access articles, information, and resources that help officers across the United States protect their communities and stay safe on the streets.

Burglaries and other thefts were the primary complaints in Morrow County circa 1985, but there were four or five murder cases and two bank robberies during Drago’s stint as Sheriff.

Sheriff Drago was not station-bound. He responded to calls and made some landmark arrests. In one of the murder cases, he apprehended the suspect as he tried to leave the crime scene, carrying a rifle.

Every law enforcement agency has its “frequent flyers” — people who seem to get arrested on a semi-regular basis — but Morrow County’s (population about 300, at the time) frequent flyer of the time made a real name for himself. John Krebs robbed the Ione branch of the Bank of Eastern Oregon in 1983. He was more than familiar with the bank. His grandfather founded it. Krebs was convicted and sent to the Oregon State Penitentiary, but he and another inmate escaped in 1985.

Krebs went back to what he knew best. He and his accomplice robbed the same bank, almost two years to the day after his first robbery. Several witnesses outside the bank saw them struggling with their masks, waving their guns around inside, and driving away.

They ditched the first getaway car and took another when Sheriff Drago spotted them and gave chase. They stopped for a moment to yell “F--- you, Drago!” out of the window and tried to back the car over the sheriff. Sheriff Drago fired one shot, and the car took off again. Shortly afterward, an Oregon State Police trooper managed to block their path, and the robbers, along with two women and a baby in the car, were arrested.

Krebs got 30 years in prison but managed to escape again from the sheriff’s car that was taking him to prison. He was recaptured and eventually served his term.