Things were looking a bit grim for former boxing Welterweight Champion of the World William “Mysterious Billy” Smith and his partners in almost-crime, brothers Harry and Jim White.

They had learned the trade of a Portland waterfront boarding master/crimp/shanghaier at the feet of the master — the legendary Larry Sullivan. Now they had dared to go into business on their own, in competition with their former mentor, and Larry was not having it.

Larry’s usual procedure in such cases was to chase down the offending competitor and put him in the hospital. He was a former professional middleweight boxer and more than a match for 99 percent of all Portland men.

But he was not a match for Mysterious Billy — a former world champion — and he knew it.

So instead, Larry, through his political connections in the ruling Republican party, arranged for the state government to legislate a monopoly for him. The legislature promptly established a boardinghouse commission — supposedly in response to a sharp rise in the market rates for sailors’-boardinghouse services.

This new “state shanghaiing commission” moved immediately to declare that it was going to license only one crimping outfit: Larry’s. It promptly issued a license (and a pin-on badge of the kind law-enforcement officers wear) to Larry, and a cease-and-desist letter to Mysterious Billy and his pals.

Of course, they weren’t about to take this lying down.

Naturally, the first thing they did was to challenge the commission’s authority in court. But that sort of thing takes time — so, rather than go out of business for a year and wait, or continue doing business furtively, they adopted an attitude of open defiance.

“On that license business? What do I care about a license?” Harry White said, during an interview with an Oregonian reporter that ran under the headline “HE IS SHIPPING SAILORS: Harry White does Not Worry about the Law.”

This, of course, would be a dangerous attitude to take toward the law under ordinary circumstances. But there seems to have been a widespread awareness that the boardinghouse commission wasn’t a real regulatory agency. Its authority was not much respected on the waterfront. Perhaps that had something to do with the fact that, although charged with enforcing the laws against illegal abuses such as boarding ships without permission and overcharging for services, it showed no interest in doing anything of the sort. The only enforcement action it seemed interested in was ordering Larry Sullivan’s competitors to leave the business.

Meanwhile, the Whites’ lawsuit against the commission was making its way up through the courts. It finally made it to the Supreme Court in 1904, and the verdict was sharp and incisive: No, the state was not allowed to create a monopoly in restraint of trade.

The wailing and gnashing of teeth in the subsequent issue of the Oregonian that followed this devastating blow comes off as almost surreal to a modern reader.

“SHORN OF POWER,” screams the headline, followed by the then-usual stack of sub-headlines: “Boarding-House Commissioners Disgusted./ PRICE OF TARS MAY GO UP/ Trouble as to High Charges May Be Renewed./ THEORISTS ARE CRITICISED/ Shipping Men Are Generally Satisfied with Operation of Law which the Supreme Court Declaration has Practically Invalidated.”

“When I was urged, much against my will, to serve on the board, the assurance was that we were to have full power to regulate the business for the best interests of the port,” sniffed commission president E.W. Wright. “Now that the court has decided that we have no such power, it is useless to be bothered any further … I do not feel justified in 
wasting any more time with it.”

The Oregonian, always a reliable voice for the Portland political establishment back in those days, was clearly sympathetic to the commission’s goals. But its journalists did have the grace and professionalism to talk to some of the opposition, too — not Mysterious Billy or one of the White boys, but James Laidlaw, the British consul, whose job it was to look out for British sailors of the grain fleet and whose acerbic letters to the editor about the evils of the crimps were a regular sight in the Oregonian. His comment cut right to the heart of the matter.

“The commission has full power to revoke licenses for enticing sailors to desert or charging unlawful exactions,” he said. “If the present commissioners feel powerless, perhaps others can be appointed to enforce the law.”

“One set of crimps is no better than another, (so) why grant one set a monopoly?” he continued. “If one set struts in immaculate linen and fine clothes and lends its presence to the state legislature, that does not prove superiority. In fact, it doesn’t make any difference so far as I can see.”

Ah, but it made all the difference in the world, as Laidlaw surely knew well. (The reference to fine clothes and the state legislature was an obvious shot at the always-spiffy and politically active Larry Sullivan.) Certainly Laidlaw can’t have been much surprised when the boardinghouse commission, shorn of the one power which likely constituted its entire reason for existing, disappeared from the scene.

By the time this whole drama was playing out, though, the crimping industry in Portland was in obvious decline. The grain fleet was switching over from sails to steam. Steamships were much more sanitary and comfortable than sailing ships, the food was much better, and the crew members on them, once they’d secured a berth on one, were extremely loath to put it at risk by checking into a boardinghouse. The few who did so ran a pretty high risk of ending up back on a sailing ship with slim prospects of returning anytime soon.

Plus, Portland was gearing up for the 1905 Lewis and Clark Centennial Exposition, and had elected a new mayor, Harry Lane, who was on a crusade against the squalor and vice that characterized the North End. Not coincidentally, the train station in which all the crowds of visitors to the Expo would be arriving — the Union Station — was literally at the north end of the North End. Visitors would have to travel all the way through Portland’s worst neighborhood immediately upon arrival. If things were not cleaned up, their first impression of Portland would likely be one of seedy saloons, drunk sailors, and winking prostitutes.

Sullivan, sensing the shift in political winds, made a last-ditch attempt to get himself elected to the city council. When, in spite of his considerable voter-fraud resources, he lost, he left Portland for Goldfield, Nev., where he promptly involved himself in what historian Barney Blalock calls “one of the greatest bunco schemes ever perpetrated — a multi-million-dollar banking and mining concern that bore the name ‘Sullivan Trust Company.’” The story of Larry’s adventures in Nevada will be the topic of a future column.

Billy, though, stuck around. The White brothers stuck around too, taking care of the dwindling business in tall-ship sailors clear into the 1920s. Jim, after serving a one-year prison stretch for shanghaiing a sailor, decided the job was too rich for his blood and quit, but Harry carried on. In the 1920s, after all risk of non-homeless men actually being shanghaied was gone and it was “safe” to joke about such things, he adopted the nickname “Shanghai White” and continued serving the dwindling grain fleet through at least 1928, possibly later.

Billy remained a colorful Portland character. In 1910, he was in the news for socking a socialist agitator in the kisser during an argument over politics. The following year, his ex-wife’s new husband emptied a five-shot revolver at him, hitting him four times and nearly killing him. He survived, though, apparently without permanent injury.

I haven’t been able to learn what Mysterious Billy did during Prohibition, but all things considered it’s a pretty safe bet that it involved moonshine in some way.

After Prohibition ended, he opened a new saloon, a beer joint this time, at 15th and Wheeler in Albina. He called it The Champion’s Rest, and that’s exactly what it was. The onetime slugger, shanghaier, and bar fighter finished his days pouring beer and reminiscing with his customers as the host of one of pre-war Portland’s favorite watering holes. He died in 1937.

(Sources: Portland’s Lost Waterfront and The Oregon Shanghaiers, two books by Barney Blalock published in 2012 and 2014 respectively; Portland Morning Oregonian archives from 1903, 1904, 1910, and 1911)

— Finn J.D. John teaches at Oregon State University and writes about odd tidbits of Oregon history. His book, Heroes and Rascals of Old Oregon, was recently published by Ouragan House Publishers. To contact him or suggest a topic: or 541-357-2222.

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