OR Man ‘Loony Toon’ Sentenced To 20 Years After Police Chase Shooting In Milwaukie

MILWAUKIE, Ore. (THECOUNT) — Loony John Franklin Kolb Toon, 43, pleaded guilty Thursday and was sentenced to 20 years in prison after authorities said he led Oregon police on a dangerous 2025 pursuit during which he fired shots at officers.

According to the Clackamas County District Attorney’s Office, Toon pleaded guilty to multiple felony charges including four counts of first-degree attempted assault with a firearm, unlawful use of a firearm, felon in possession of a firearm, and second-degree escape.

The case stems from a June 20, 2025 traffic stop conducted by Milwaukie police shortly before 3 a.m.

Officials said officers stopped a vehicle occupied by Toon and a female passenger. After discovering Toon had an outstanding felony warrant, another responding officer deployed spike strips beneath the vehicle’s rear tires in an attempt to prevent him from fleeing.

Investigators said Toon — who previously went by the name John Kolb — reversed into a police vehicle, drove over the spike strips, and sped away along Highway 224.

During the ensuing pursuit, authorities allege Toon fired a pistol from the vehicle window toward pursuing Milwaukie police officers.

The chase ended after Toon’s vehicle crashed near railroad tracks at Southeast Tacoma Street and 26th Place in Portland.

Police said Toon then fled on foot into the Eastmoreland Golf Course area. Despite an extensive search involving multiple agencies, officers were initially unable to locate him.

Toon was later arrested in Sandy, Oregon, on June 23, 2025.

Clackamas County Deputy District Attorney Rebecca Wareham Portlock described the incident as “incredibly dangerous,” stating Toon “showed callous disregard for every single person in his path” and endangered multiple police officers.

Authorities said Toon was already on probation in Columbia County at the time of the incident for first-degree attempted kidnapping.

As part of a global plea agreement, officials said Toon will also plead guilty to outstanding criminal cases in Washington, Benton, Yamhill, and Columbia counties. Those sentences will run concurrently with the 20-year Clackamas County prison term.

Court officials further ordered Toon to pay restitution to the City of Milwaukie for damage caused to a police vehicle, as well as compensation to the owner of another vehicle struck by gunfire during the pursuit.

According to prosecutors, Toon has an extensive criminal history involving 25 prior convictions, including 16 felonies.

Milwaukie is located in Clackamas County just south of Portland in northwestern Oregon.

Google Maps: Milwaukie, Oregon

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