McNeil Island prisoner William Dempsey was one of three convicts on a road gang who escaped the Washington State prison in 1940.
Dempsey and two other road-gang prisoners took advantage of dense fog conditions on January 30, 1940 to attempt a getaway from the southeast Puget Sound prison.
They left behind picks and shovels, and risked drowning to attempt to swim to shore.
A two-time murderer, Dempsey’s break came after serving 20 years of his life sentence. He thought a breakout was his last chance for freedom after two parole hearings went against him.
Dempsey hailed from the slums of Cleveland. He served a stretch in an Ohio reformatory for petty larceny in 1917.
He hightailed it to Alaska by 1919. He changed his Polish name to Dempsey and used other aliases such as Harry Goodfellow (a popular silent film actor).
At five feet and eight inches, he was a scrapper with numerous scars on his neck, forehead, shoulders, hands and wrist. He had gray eyes and wispy brown hair.
Authorities apprehended two of the three exhausted escapees.
Notably, convict Cyril Armer was covered in machine shop grease when a patrol boat cut his swim to freedom short.
Dempsey, then 40, apparently made it to shore despite exposure to the water and elements.
A search of the waters and the 4,000-acre island by bloodhounds and 175 penitentiary employees came up empty.
Mrs. Ace Mallory of Gig Harbor told police a drifter approached her to beg for food. She identified a mug shot as that of Dempsey, according to a Kitsap Sun article.
A headline in the Bremerton Daily News of February 3, 1940, read: “Fugitive from Prison Given Food, Money by Minister Thursday.”
The Daily News said a minister acknowledged befriending a bedraggled man wearing a slicker.
The man, thought to be Dempsey, pleaded for food and cash to take a ferry from Bremerton to Seattle.
That’s when the trail occupied by law enforcement and bloodhounds went cold.
Warden E. B. Swope told news media that Dempsey may have clung to a piece of driftwood and paddled his way from the island to the Olympic Peninsula. Swope announced a $50 reward.
Swope resigned 10 weeks after the embarrassing escape to become warden of the federal prison in Terre Haute, Indiana.
Dempsey claimed to be 19 when he turned cold-blooded killer. He bludgeoned a woman named Margaret (Marie) Lavor with a sandbag during a 1919 Anchorage robbery. He concealed her corpse. A dog led searchers to her body stashed by Dempsey in a well.
Alaska Territory Judge Charles E. Bunnell, destined to become the University of Alaska’s first president (1921-1949), accepted a Valdez trial jury’s guilty verdict. Bunnell imposed a death sentence. Bunnell chewed out Dempsey for misbehaving in court.
Deputy Isaac Evans, 54, transported Dempsey to the federal jail in Seward. He failed to search the prisoner’s bundle of clothing.
A gunfight ensued. Dempsey fired eight shots from a concealed .38 automatic Colt pistol, according to the Juneau Empire of Sept. 5, 1919.
After plugging Evans whose shots went wild, Dempsey commandeered a railway handcar. A posse recaptured him three days later and disarmed him.
Scheduled to hang in Valdez in 1920, Dempsey caught a break.
President Woodrow Wilson, an opponent of the death penalty, switched Dempsey’s punishment to life imprisonment. Wilson commuted or rescinded convictions of 2,480 persons.
Wilson’s action came “considerably to the disgust of Alaskans in general,” according to the Cordova Times of July 10, 1920.
“A notorious murderer was in our town during the Fourth,” the paper said. “He was down at the dock on board the Northwestern” in custody of federal deputies.
Dempsey, a laborer, might have used his “model prisoner” demeanor to blend into society and to avoid detection. Likely he invented a name and covered those scars as best he could.
Dempsey, while incarcerated, tried to regain freedom by becoming a trusty, but Bunnell issued two thumbs-down parole recommendations.
The prisoner Bunnell deemed unsuitable for parole never risked his freedom by coming after the former judge.
Hank Nuwer writes books and journalism while based in Fairbanks. He and his photographer wife Gosia love visiting remote Alaska villages and landmarks. In May 2024, the Alaska Press Club named him columnist of the year.
This column originally ran in the Aug. 2 issue of The Cordova Times.