COTTAGE GROVE SENTINEL • SEPTEMBER 26, 2018 •
9A
Off beat Oregon History: Midnight bootleggers’ jailbreak
By Finn J.D. John
For The Sentinel
Around 10 p.m. on the night of
Saturday, March 19, 1932 — just
a few months before Prohibition
was ended — four vehicles rolled
furtively into the little Coast
Range town of Toledo.
A big, important-looking se-
dan led the caravan, followed
by two large trucks and fi nally a
sleek Buick coupe. In the coupe,
two men sat cradling machine
guns. Th e nine men in those
vehicles weren’t tourists. Th ey’d
come to Toledo to get three of
their business associates and
bring them back home to Cana-
da — with their luggage.
It wouldn’t be an easy rescue,
though. Th eir friends weren’t
staying in a Holiday Inn. Th ey
were locked away in cells at the
Lincoln County Jail. And their
“luggage” was more than a cou-
ple of beige Samsonite bags; it
consisted of roughly 400 cases
of bonded Canadian whisky,
rum, and brandy, along with
several dozen 15-gallon cans of
190-proof straight alcohol. And
it was locked securely away in the
jailhouse evidence room.
Th e three men in the jail that
night were the crew of the 36-
foot Canadian motor yacht Sea
Island, which had run onto the
rocky reef in the mouth of Whale
Cove while making a midnight
liquor delivery there a few weeks
before. Th ey’d buried the booze
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on the beach and tried to beat it,
but they’d crashed their car near
Hebo, drawing police attention
when the wreck was discovered
to have switched plates; the word
had been passed along, and the
three Canadian mariners had
been arrested as they stepped off
the bus in Portland, and brought
back to Toledo to await trial on
bootlegging charges.
Now their friends were there
to bust them out of the joint in
proper gangster style.
Th e party was delayed a bit
when a Lincoln County Sher-
iff car rolled into town, passed
them, and pulled into the county
garage. But, a few minutes later,
the deputy pulled out again and
was gone. Around 11 p.m., the
Rotary
Club of
Cottage
Grove
coast was clear, and it was show-
time.
Th e smaller of the two trucks
pulled up near the jailhouse, and
Portland resident S.U. Carrick
lugged an oxyacetylene cutting
torch into the building. In about
15 minutes he had the locks cut
off of all the intervening doors,
and the three once-and-future
prisoners were at liberty.
Th ere followed a lively debate,
according to the testimony of the
other prisoners. Th e three Cana-
dian mariners felt that breaking
out of jail was a bit much; they
thought it would be better to stay
and face the music. But the leader
of the rescue party, international
motorcycle racer and Portland
resident Paul Remaley, assured
them that they couldn’t be extra-
dited for a mere jail-break. Th e
jailbirds weren’t too hard to con-
vince. Th ey didn’t really want to
stick around.
Meanwhile, Carrick had al-
ready gotten busy cutting his
way into the evidence locker,
and once this was done the other
nine men hastily started lugging
boxes of booze out to the waiting
trucks. All the while, the men in
the Buick peered over the front
sights of their machine guns into
the darkness, watching and lis-
tening for any signs of trouble.
Luck was with them (more luck
than they could probably imag-
ine, actually), and a few minutes
later the Canadians, reunited at
last, were piling into their vehi-
cles. Th e gunmen in the Buick,
their job done, disappeared into
the night; and the others got their
rigs started and pointed them
north, toward home.
Meanwhile, unbeknownst to
all, they had been ratted out. A
vague, anonymous phone call
had come in to Portland author-
ities warning that something was
going to happen in Toledo that
night. Th e warning had been
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passed on to the state police, and
a couple of squad cars had been
dispatched to check things out.
Th e state cops were about 20
minutes from Toledo when they
passed the caravan rolling north-
ward: one sedan and two large
trucks. It wasn’t unheard of for
legitimate trucking companies to
be hauling stuff around at night,
but it was unusual enough to be
noticed as the cops — who still
didn’t know anything had hap-
pened in Toledo — approached
the town.
But when they got there, and
learned what had happened, they
fi gured it out right quick. Th ey
jumped back into their cars and
raced out of town in pursuit. Th e
trucks had a long head start on
them. But they had one huge ad-
vantage: Th e vehicles had passed
each other in the dark of night,
and the drivers of the caravan
hadn’t been able to see any of the
details of the two cars that had
passed them as they drove out
of Toledo. Th ey had no idea that
the heat was on. So they contin-
ued driving northward at normal
speeds. Th en they stopped the
two trucks. Th e smaller truck,
with the welding kit in it, needed
gasoline; and the cans of gas for
the trip were in the larger truck.
So the bootleggers got busy
refueling. Th ey were still refuel-
ing when two carloads of Oregon
State Police troopers rolled up on
them, guns drawn.
Th e cops quickly learned that
the sedan had gone on ahead.
Th ey were pretty sure that if they
pulled up behind it in their cop
cars, the driver would hit the gas
hard and might actually get away;
or a rolling gunfi ght might break
out, and someone could get hurt
or killed. So instead of risking
that, several of the troopers who
were in civilian dress hopped
into the trucks and drove on into
the night. Th ey fi gured by the
time the people in the sedan fi g-
ured out that they weren’t who
they thought they were, they’d
be covering them with their ser-
vice revolvers and the jig would
be up.
Th e ruse worked. Th ey soon
caught up with the sedan, which
had pulled over to wait for them,
and by the time the people in
the car realized what was going
on, they were already looking
into the barrels of .38s.
Th e Lincoln County jail fa-
cilities no longer being in suit-
able condition for guests, the
bootleggers were brought to the
Benton County jail in Corvallis
instead. In court, the Canadian
gangsters and their local asso-
ciates were aff able and colorful.
Th ey promptly posted bond
— Remaley used his one phone
call to tell someone named
Frank to grab $13,500 in cash
and come to Corvallis to bail
him out. Carrick, the one who
had cut the locks off the jail-
house doors, cheerfully off ered
to fi x the jail for them, free of
charge
Th e men were all convict-
ed, of course, on various liquor
and prison-break charges, both
federal and state off enses. But
by the time they’d served their
relatively short state sentences,
Prohibition had been repealed,
and the federal charges were
dropped.
Several sources add a few fi nal
details to this story. According
to these, the jailbreakers had in
fact started a fi re that damaged
the Toledo jail heavily, and in
lieu of prison some of the Cana-
dians were sent back to Toledo
to help repair it. When Prohibi-
tion was repealed in 1933, they
were set free, and they headed
back to Canada.
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