Smitty the Bootlegger

Here is another warm up exercise for my new book about Portland during Prohibition. A violent story about one of Portland's most vicious and colorful criminals.

Prohibition was an extremely unpopular law and enforcement was done so unfairly that it became very popular to resist the law.  Drinking became even more popular than it had been before it was outlawed.

            Wee Willie Smith, aka Smitty the Bootlegger, was one of Portland’s most colorful and violent bootleggers during Prohibition.  Smith, like many of Portland’s gangsters, was an athlete as a young man, but his sport was unusual – cricket.  This may have had something to do with his size. Smith was a small man who often went by the nickname Shorty.  No matter how small he was Smitty the Bootlegger was vicious, especially to cops who tried to arrest him.

            Shorty Smith often worked with Roy Moore’s gang and enjoyed the protection the “king of Portland bootleggers” afforded by his cozy relationship with the police.  Although Smith was arrested twice for assault with a deadly weapon, once for murder and numerous times for possession of alcohol and narcotics, he rarely served time in jail.  He was acquitted more than once and he usually got off with a fine if any punishment was exacted.

            Smith, who worked off and on as a taxi driver, started his criminal career with drug dealing for which he was arrested in 1920 and 1922.  By 1923 he had connected with Moore’s gang and was providing muscle for liquor distributors such as Jack Phillips and C.B. Corcoran.  Jack Phillips was Portland’s own version of Jay Gatsby; a talented and well-known student at Jefferson High School who returned from the Great War with a big thirst for booze and for money.  Phillips and Smith were sitting in C.B. Corcoran’s car near the corner of SW Eleventh and Jefferson on the night of February 2, 1924 when the first recorded violence of William Smith’s career occurred.

Wee Willie "Shorty" Smith aka Smitty the Bootlegger, part-time taxi driver, full-time criminal, was one of Portland's most colorful and violent bootleggers.

            Dr. J.A. Linville, 62 year old head of federal Prohibition enforcement in Oregon, stepped out of a shoe store on Eleventh and walked toward his car with his assistant William Kellar. The two Prohibition agents saw Corcoran’s car with the three men in it parked behind theirs and recognized it as a “bootlegger’s rig.”  Approaching the car Linville stepped onto the running board on the passenger’s side and confronted Corcoran, who was at the wheel.  Corcoran jammed the car into reverse and quickly backed up about eighty feet, smashing Linville into two telephone poles and a few trees, and dragging him most of the way.  Kellar ran up on the driver’s side and jammed his pistol into Corcoran’s ear, bringing the car to a halt and saving his boss’ life.

            Linville was badly bruised and several ribs were broken.  His clothes were almost completely ripped off, but he helped Kellar take Corcoran, Phillips and Smith into custody before collapsing. Smith and Phillips claimed they knew nothing about the nine gallons of whisky packed into the car, but Smith had a pint in his pocket and all three were arrested for possession of alcohol.  In court all three men pled guilty to liquor possession and were fined $500 each, charges of resisting arrest were dropped.  The fine was hefty, the equivalent of nearly $7000 each today, but it didn’t seem proportional with the physical harm Linville suffered.

            Smitty the Bootlegger went back to making liquor deliveries and providing muscle for Roy Moore’s gang, but somewhere he met Lillian Foley and added a new scam to his repertoire. Foley aka Blondie, a down and out alcoholic with a record for prostitution, would entice men to her room with promises of booze and sex.  Smith, in the next room with a weapon, would wait for an opportune moment and burst in on the couple and with threats extort money from the victim.  It’s an old con called the Badger Game. There is no way to tell how many times Shorty and Blondie pulled their scam or how many skid road hotels they used, but they were set up at the Arcade Hotel on February 17, 1925 when Willie Smith shot police “secret agent” John Fagerlie.

            The shooting of Fagerlie, better known as Handsome Hans, may have been a deliberate attempt at murder or it may have been a misunderstanding as Smitty claimed.  Although Moore enjoyed protection from the police, the violent methods of his gang must have rubbed Chief Leon Jenkins the wrong way.  Whether Handsome Hans was out to get Moore’s gang or not, he was an obvious target for a hit. Fagerlie, a former logger who had been arrested in a speakeasy, was a very efficient “stool pigeon.”  Handsome Hans passed his time spending freely in brothels and blind pigs (illegal drinking parlors) and gathering evidence that could be followed up by the Raiding Squad.  In just the first six weeks of 1925 Fagerlie had been responsible for more than thirty arrests.

John "Handsome Hans" Fagerlie, undercover "secret agent," nearly died when Shorty Smith shot him through the lung.  He survived but retired from police work after the shooting.

            Whether Wee Willie Smith deliberately tried to kill Handsome Hans or not, he didn’t succeed. Fagerlie was badly wounded and nearly died, but slowly recovered. The wound forced Handsome Hans to retire from police work, though so in that sense the shooting was very effective.  Smith’s next murderous attack lends credence to the idea that Wee Willie worked as a hitman, but details are too sparse to say for sure.

            After being acquitted on a charge of assault with a deadly weapon, Smith married Foley and they set up housekeeping in an apartment on SE Ankeny.  They continued their nefarious business and Smith was arrested several times for possession of liquor.  He paid a fine of $300 for one arrest, but seemed to still be enjoying some level of protection. 

            The police were involved in the liquor business in order to contain it and violence was not part of the plan.  Roy Moore’s gang was dismantled in 1928 and the “king of the bootleggers” went to McNeil Island for a few years.  Violent rivals, such as the DePinto brothers tried to take over Moore’s business, but the Police Bureau proved to be good at eliminating competition.

Lillian "Blondie" Foley Smith was Smitty's wife and accomplice.  Her job was enticing victims back to her place with promises of booze and sex.

            It is unclear whether Samuel Taylor was working for the police when he hooked up with Lillian Foley Smith in August 1933.  He was a logger, like Handsome Hans had been, and he was a brother-in-law of police sergeant Lawrence Russell, so it is very possible that Taylor was a “secret agent” as well.  The set up was very familiar: Just like Handsome Hans, Sam Taylor met Blondie and was lured to her premises with promises of booze and sex.  Taylor went along, most likely with the intention to gather evidence for a search warrant.  Wee Willie, as usual, was hiding in the apartment with a weapon, this time a blunt instrument.  At some point Willie jumped out and beat Taylor to death.

            Just like before Smith claimed self defense, saying that the fight started when Taylor insulted his wife, Lillian.  Smitty lied on the witness stand, saying he only hit Taylor with his fists a couple of times.  Autopsy showed that Taylor had suffered a severe beating with a heavy object. Lillian backed up her husband’s story and juries always seemed to like Wee Willie.  After a few months in jail Smith was acquitted and released in April, 1934.  By that time the old order had passed. Mayor Baker was in retirement; Leon Jenkins was Inspector of the Night Watch; a new generation of underworld characters were ready to take over Portland’s vice industry.  Things may have gotten too hot for Smitty the Bootlegger, because he and his wife disappear from public records after his acquittal. Maybe they left town.

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