Washington County cops have long been on the lookout for a 42-year-old career criminal named, coincidentally enough, Jason Sherriff.
Sherriff has been eluding police in Washington County since at least 1997. When police pull him over, he has long favored a dubious strategy: speed off. Over the years, he’s crashed into a ditch, a house and even a police car that was boxing him in as he attempted to flee.
Sgt. Eric Stoneberg, 20-year veteran of the Washington County Sheriff’s Office, took pride in training deputies how to eventually catch criminals like Sherriff, who seems to enjoy leading cops on high-speed chases through quiet Hillsboro neighborhoods.
But car chases, long a staple of Hollywood thrillers and the nightly news, have gone out of fashion.
For one thing, they’re dangerous. Researchers estimate that around 300 people die from police pursuits nationwide every year. A third are innocent bystanders, including a 40-year-old Portland woman killed earlier this month by a silver Buick Regal driven by a suspected armed robber who was being pursued by a Gresham police officer.
For this reason, policymakers don’t like car chases. In recent years, law enforcement agencies across the country are having cops chase less, telling them to focus only on reckless and dangerous drivers. In 2021, the state of Washington banned cops outright from chasing drivers suspected of low-level crimes. (This year, legislators in Olympia rolled back some of the restrictions.)
This is the story of a prolific criminal—and the cop who quit his job after being told not to catch him.
Sherriff, 42, is what’s known among cops as a “frequent flyer.” He’s been in and out of Washington County Jail his entire adult life: DUIIs, criminal trespass, theft, gun charges, drug dealing. His jail file currently contains 36 different mug shots. He’s been convicted 17 times and served a three-year stint recently in an Oregon prison.
“We know his history,” Washington County Sheriff’s Sgt. Danny DiPietro says. “We know he’s going to run, we know he’s going to fight, and we know he’s in possession of guns.”
Sherriff has been charged with fleeing police seven times, starting when he was 16.
The next time was in 2007, after he fled deputies in a stolen Land Rover and drove it into a drainage ditch. He then ran on foot. After police dogs failed to track him down, a SWAT team arrested him at a house a week later. He was convicted of reckless driving and sentenced to six months in jail.
In 2014, he slammed a black Nissan Pathfinder into a Hillsboro house after cops tried to pull him over. Someone was transported by ambulance to St. Vincent’s Hospital, according to dispatch records reviewed by WW. It’s not clear from those records who was hospitalized—Sherriff or someone in the house—but prosecutors later asked for a weightier sentence given that his behavior “posed a threat of actual violence toward a witness or victim.”
Sherriff was convicted on reckless endangerment charges and again sentenced to six months in jail.
Sometimes cops chase Sherriff and sometimes they don’t. It’s dangerous, explains Hillsboro Police Officer Zac Storm. And besides, officers know where he hangs out and can always arrest him later.
“People who run always get caught in the end,” Storm says.
In recent years, the Washington County Sheriff’s Office has decided to limit car chases “to drivers who pose an imminent threat of death or serious physical injury to another person,” according to the department’s annual report. Washington County followed a similar policy shift at the Portland Police Bureau, which allows pursuits only in limited circumstances: reckless drivers or felony suspects.
“Vehicle pursuits present a unique and dynamic challenge that requires split-second decision-making. The increased risk of injury or death to innocent community members, deputies, and occupants of pursued vehicles cannot be overstated,” the Sheriff’s Office explained in a statement.
Meanwhile, the number of police car chases in Washington County plummeted. According to the sheriff’s annual reports, there were 43 in 2018 and, most recently, 26. (The Multnomah County Sheriff’s Office doesn’t publish similar reports. PPB says chases have dropped from 197 in 2016 to 23 in 2022.)
Sherriff continues to flee police. He’s been charged with “felony elude,” meaning he sped off in a vehicle, four times in the past two years. The final time, on Feb. 22 of this year, he was arrested.
Washington County wouldn’t tell WW exactly what happened in any of the four cases. They’re still being investigated.
But a sheriff’s spokesman did confirm that when deputies arrived at a known hideout Dec. 12, Sherriff fled. He rammed a vehicle into a patrol car after it attempted to box him in.
Three days later, Lt. Mitch Coley, who oversees westside patrol, told his deputies to back off, according to an email that surfaced in a subsequent legal case.
Deputies could respond to 911 calls involving Sherriff, Coley wrote, but should stop pursuing him.
“Given the repeated eludes by Jason Sherriff, and that he is known to carry firearms, please do not actively pursue him—this includes not developing missions to capture him,” Coley wrote.
One month after the order, Sgt. Eric Stoneberg wrote a message protesting the policy to the other on-duty sergeants on his in-car computer, according to a lawsuit later filed in Washington County on behalf of Stoneberg.
He sent the message as a dozen Washington County deputies were coordinating a mission in January to arrest Sherriff, says Dan Thenell, Stoneberg’s attorney.
Stoneberg wrote: “Jason Sherriff should not leave that street. Period. The end. And we should pursue him and get him into custody.”
It’s not clear the mission ever happened. Sherriff wasn’t arrested that day. But Stoneberg, the 20-year veteran, was charged with insubordination two months later, in March.
Stoneberg was demoted to corporal the following month. He resigned in July and is now a rank-and-file deputy in Yamhill County.
He’s suing the Washington County Sheriff’s Office but declined to comment for this story.
As recently as last month, Sherriff led Portland police on a wild chase.
Sherriff was seen swerving across lanes of oncoming traffic in deep Southeast Portland. Police flashed their lights to pull Sherriff over, but instead he sped off.
The cops, who believed his reckless driving was “likely to result in death or serious injury,” gave chase—but not by car. The bureau dispatched one of its aircraft.
The pilot reported that Sherriff had crashed his car a few blocks away near a church. Sherriff fled on foot, but a police dog helped track him down. He’s now, once again, in Washington County jail.
At the time of his arrest, Sherriff had outstanding warrants for seven different felony charges. Now, Portland police say, they’re adding an eighth: hit-and-run.