The newspapers heralded him as “Portland’s Al Capone.”
That was overselling it. Paul Remaley never ordered the mass murder of his enemies, like Big Al supposedly did with the St. Valentine’s Day Massacre. Nor did he have hundreds of police officers, judges and politicians on his payroll.
But he could be just as daring and flamboyant as the famous Chicago gangster in other ways. That made him, in the eyes of the local public, the “big shot in Oregon’s liquor racket” during Prohibition.
There was a lot of money to be made in bootlegging in the 1920s and early ‘30s, but it was not a particularly romantic undertaking. The hours were bad, the competition brutal. One ambitious Oregon booze smuggler, Roy Moore, hatched a plan to cut off the ear of Remaley’s right-hand man, “for a souvenir.”
Remaley’s Portland-area celebrity actually predated his bootlegging operation. The Pennsylvania native first came to the public’s attention not as a criminal but as a motorcycle racer.
Acting as sort of a test pilot during this early stage of the automobile era, he twice set the “three-flag record” with a sprint from the Canadian border to Tijuana on his Indian Scout motorbike. His best record-setting time was just over 43 hours.
“Believe me, making a three-flag record isn’t any holiday stunt,” the 21-year-old Remaley declared in 1923. He said he trained hard to handle the machine and the terrain, and to go without sleep for many hours.
He reported that, during his second record-breaking ride, a deer in southern Oregon had raced along beside him for quite a while, so close he “could almost kick the animal.”
(The Oregon Journal celebrated Remaley’s high-speed skills, adding that, “in passing through all towns, Remaley was careful not to violate any of the traffic laws.”)
Pushing motorcycles to their limits was good for a headline here and there, but it didn’t provide much of an income. Which was why rumors of a criminal life started circulating after Remaley bought what was described as “an elaborate home” at 1248 Royal Court in Portland’s Laurelhurst neighborhood.
The rumors proved out. Remaley resurfaced in the news in February 1932 after a motorboat ran aground in Whale Cove, near Depoe Bay.
The billowing smoke drew local residents toward the beach. The boat was burning out of control.
The rumrunner’s three-man Canadian crew managed to spirit the boat’s precious cargo to land, where they hid their 301 cases of bonded liquor on the beach. Then they hopped on a bus.
Law enforcement quickly found the liquor stash and carted it away. As the officers drove off, townspeople descended on the beach in hopes that the authorities had overlooked a case or two.
Prohibition agents, given a heads-up by coastal police, were waiting for the Canadians at the bus depot in Portland. They arrested the three bootleggers and took them to Toledo, locking them up in the Lincoln County Jail. They stored the booze in the jail as well.
That appeared to be the end of that, but then the story took a turn so unusual for Oregon Prohibition history that all these years later the Oregon Secretary of State’s Office has a webpage devoted to the plot twist.
Five weeks after the rumrunner sank in Whale Cove and its sailors were arrested, Paul Remaley and two other shotgun-toting men slipped into the Lincoln County Jail late on a Saturday night. They used an acetylene torch to cut through the cells’ steel doors, freeing the Canadians. They also freed the confiscated booze and loaded it onto two trucks.
A third vehicle, a Buick sedan, carried two men wielding machine guns. The Oregon Journal would call the assault on the jail “the closest Oregon came to brash gangsterism.”
The getaway didn’t go nearly as well for the “Remaley Gang” as the jail break. The two trucks and the Buick coupe headed up the coast along the main road, and the car soon managed to get too far ahead. Unbeknownst to the bootleggers, the state police had received a tip about the breakout and were gaining fast. When the Buick and its tommy guns disappeared around a bend in the road, state police stopped the trucks.
“Police Escape Battle by Narrow Margin,” The Oregonian proclaimed.
The coupe eventually pulled over to wait for the trucks to catch up, and officers took the car’s occupants by surprise, arresting them without incident.
One of the bootleggers, Sidney Carrick, told authorities they were lucky Remaley wasn’t on a motorcycle, for they never would have caught him.
“Remaley is some motorcycle specialist,” he said. “He took me through Portland at 70 miles. I told him I’d rather the cops would get me.”
With the Lincoln County Jail in a shambles, police took the six tons of illicit liquor to Portland’s custom house for better safekeeping. By now, people across Oregon were following the bootleggers’ exploits in the newspapers, and so a large crowd met the booze when it arrived at the building.
“I hope this stuff stays here,” state police Corporal Ira Warren said as he stood in front of the custom house. “I have seized it twice, and that should be enough.”
Remaley was convicted and sentenced to five years in prison for the jail break. His partners in crime received similar sentences. (Rumors abounded that the Lincoln County sheriff was in on the operation, but a grand jury would conclude that the allegation was “absolutely groundless.”)
Eventually, the confiscated liquor was sent to Vancouver Barracks to be used for “medical purposes.”
Remaley spent almost two years in the state penitentiary, but that didn’t prompt him to change his ways.
The motorcycle specialist-turned-bootlegger, who died in 1975 at 72, had found his true calling. Even though Prohibition ended a year after his jail-break arrest, he kept making and distributing illicit booze. (Liquor was legal again, but avoiding alcohol taxes — and middlemen — still meant outsized profits.)
Just weeks after his release from the state pen in 1934, Remaley was busted again, after officers discovered a large still on a ranch outside Forest Grove. The still, with a 22-foot-high copper column poking into the sky, could pump out 200 gallons of booze per day. The operation chiefly made 130-proof whisky. This time Remaley landed in federal prison for a six-year stint.
Thirty years later, he was still at it. In March 1964, law enforcement raided a rental house in Southeast Portland where Remaley and his wife lived. They found a still and 50 gallons of moonshine in a barn behind the house.
Remaley, now 61, insisted he knew nothing about the illegal-booze operation on the property.
