Offbeat Oregon – Portland’s ‘shanghai Tunnels’ are mostly myth, but not entirely

A scene from Charlie Chaplain’s movie ”Shanghaied,” which came out in 1915, several years after most historians consider the age of ”shanghaiing” to have more or less ended. Postcard image provided

One of the most popular tourist attractions for visitors to Portland is a tour of the ”Shanghai Tunnels” that run beneath Old Town’s streets.
Historians of old Portland tend to scoff at the whole enterprise. Doug Kenck-Crispin once memorably referred to the process by which the Shanghai Tunnel story developed as ”The Bulls**ttening.” Barney Blalock, Portland’s dean of living waterfront historians, is also extremely skeptical.
And they’re right … up to a point. The fact is, there is pretty good evidence that parts of the underground network we know as ”the Shanghai Tunnels” today were used to shanghai sailors. But they were used as dungeons, not as a transportation network.
The modern Shanghai Tunnel tours are the fruit of the research, exploration, and imagination (in roughly equal parts) of a Portland character named Michael Jones.
In the early 1970s, Mike Jones was the manager of a bank-cum-social-service organization called Transit Bank – ”the world’s only hobo bank” – based in Old Town.
Obviously, this put him in close contact with a lot of the exact sort of people who, clear up into the 1920s, were most at risk of being ”shanghaied”: hobos, bindlestiffs, and tramps. Some of them, in 1972, were old enough to remember those days. Others had just heard the stories from older fellows who were there. All of them were happy to fill Mike’s ear full of wild tales of the goings-on in those dark, sinister tunnels that lay beneath the abandoned, decrepit buildings along Burnside, Couch, Davis, and other streets of Portland’s Skid Row.
Mike, over the decade, collected the stories, mapped the tunnel system, and in 1979 launched the Cascade Geographic Society and went into business leading tours for the curious – regaling them along the way with the stories he’d picked up from his bank customers, augmented to some extent with extrapolations and interpretations of his own.
And that’s the storytelling foundation on which the Shanghai Tunnels tours are based today – still offered through the Cascade Geographic Society.
So, what were the tunnels, then, if they weren’t used for ”shanghaiing”?
The earliest tunnels were probably dug by Chinese merchants, to conceal and smuggle opium. Opium, in the 1890s, was perfectly legal, but heavily taxed, and smuggling it was common and lucrative.
The Chinese also had extensive illegal gambling operations that the police were constantly trying to shut down with heavy-handed raids by sledgehammer-swinging squads of bluecoats. On those occasions, when a half-dozen cops suddenly showed up and started battering away at the front door of one’s Fan Tan parlor, having a secret hidden passage connecting the joint to a laundry shop a couple blocks away was very handy.
These tunnels still were being used for their original purpose in 1914, when Oregon instituted Prohibition, and suddenly there was another useful purpose for secret underground tunnels. It’s not a coincidence that plenty of the Shanghai Tunnels today connect to drinking establishments.
And it’s that connection that makes the strongest case for the tunnels to have been used to ”shanghai” sailors. Because by far the most common way to capture a man was out of a bar.
The classic vision of a ”shanghaiing,” of course, involves a blackjack. But unless you know exactly what you’re doing, clobbering a man hard enough to knock him unconscious is dangerous business. Hit him too easy and you’ve got a bad fight on your hands; hit him too hard and you can get sent up the river for murder. It’s much easier and less stressful to chat your victim up, buy him a couple drinks, and slip a little chloral hydrate into it while he’s not looking.
”Contrary to local legend, and according to an old salt familiar with the Portland waterfront of the period, actual physical violence … was almost never used,” historian Barney Blalock writes, in Portland’s Lost Waterfront. ”Usually it was drugged whiskey in one of the North End saloons, or some sort of trickery played on young or inexperienced newcomers. Over the years, an untold number of men woke up with a terrible hangover onboard a vessel gliding down the Columbia River to the sea.”
There was a problem, though, for the aspiring kidnapper of old Portland. ”Shanghaied” sailors are like electric current – they have to be used just as soon as they’re generated – before they wake up and start yelling for a cop. So, say you’re an unscrupulous bartender at the Valhalla Saloon at First and Burnside, circa 1905; you’ve got a likely-looking prospect at the bar practically begging to be served a Mickey Finn; but the next sailing ship doesn’t disembark until tomorrow night. What do you do?
That’s where the tunnels came in.
Corvallis resident Karen Watte’s family story of the adventures of her grandfather and great-uncle – two Danish ship’s officers who made an unfortunate choice of places to have a drink – illustrates the system.
The two of them stepped into the Valhalla for a drink sometime in the late nineteen-oughts, and wound up in a sort of dungeon underneath it. Their shoes were taken from them, and broken glass was scattered around to prevent them from trying to escape. There they were held until the ship was ready to receive them.
When it was time to go, they were then given pills to take – probably at gunpoint – so that they would be unconscious for the transfer to the ship.
(In their case, the ship was delayed by bad bar conditions, and Karen’s grandfather and great-uncle woke up while it was still anchored near Astoria waiting for things to calm down. Both men dove overboard and swam to shore, to the captain’s dismay; as trained officers, they were probably his first and second mates, so it was a much bigger deal to lose them than it would have been with ordinary sailors. The two of them had to hide out with a friendly fellow Dane who kept a shop there in town while the police combed the streets looking for them.)
Were the tunnels used to actually convey Karen’s unconscious relatives to the waterfront to be loaded aboard ships? Almost certainly not. Why would they be? The scene of a couple of half-drunk sailors helping a passed-out shipmate back to his berth was very familiar to anyone who spent any time in the old North End. There was literally no way to tell if that passed-out sailor was being ”shanghaied,” or just helped to bed by his trusted friends. There was simply no reason to go to the bother of using tunnels to deliver victims.
Furthermore, during much of the year, the ends of the tunnels close to the riverbank would have been flooded. Before the seawall was built in 1928, the river often came right up into the streets of town during spring floods.
It’s that seawall that’s responsible for much of the mystery surrounding the tunnels, by the way. When it was built, dozens of buildings were demolished, and any tunnels that might have run underneath them were collapsed. By that time, the Valhalla had already met a similar fate during the construction of the new Burnside Bridge two years before, in 1926. So one can’t simply go into the tunnels and see if they lead to the river; if they once did, they sure don’t any more.
But there is one other important thing to consider about the Shanghai Tunnels. Most historians agree ”shanghaiing” more or less ended when sailing ships were replaced with the faster, safer, more predictable steamships. Why would a sailor ship out on a sailing ship when he could serve on a steamer – a much more comfortable and less dangerous job?
And so between about 1910-15, as most of the merchant marine fleet switched to steam, ”shanghaiing” petered out and was gone – so goes the conventional wisdom on the subject.
But in 1915, when the activity supposedly was a thing of the past, there still were plenty of windjammers afloat. The last windjammer built in Oregon was built in 1921, and it still was operating profitably in 1928 when it ran aground on Peacock Spit.
Where were the remaining windjammers getting their crews, in 1920 and 1925 and 1930?
They probably weren’t getting many from the ordinary run of sailors and merchant marines. There were a few old shellbacks who refused to switch to steamers, but after ’25 or so there couldn’t have been many of them left.
They clearly weren’t getting them by ”shanghaiing” ordinary loggers and farmers out of saloons and brothels, like in the 1890s.
But then, in the 1890s almost every ship in the harbor was a windjammer. By the mid-1920s, maybe the shrunken remnant of the tall-ship fleet could get by on a smaller pool of victims … drawn from Portland’s population of homeless men.
Was ”shanghaiing” still going on into the 1920s, quietly and with the tacit approval of city officials who had every incentive to support it … so long as the criminals restricted themselves to preying exclusively on the homeless?
Mike Jones got his stories and legends from hobos. A lot goes on in the ”hobo jungle” that nobody in ”respectable” society ever hears about.
Of course, there’s plenty of tall-tale telling being done there as well. But – it’s entirely possible, and in fact rather likely, that the truth content of Mike’s storytelling is quite a bit higher than most of us would like to think.

(Sources: Portland’s Lost Waterfront, a book by Barney Blalock published in 2012 by The History Press; ”The Last Word on the Shanghai Tunnels,” an article by Barney Blalock published Feb. 21, 2013, at; ”Shanghaiing in Portland and the Shanghai Tunnels Myth,” an article by Richard Engeman published March 17, 2018, at; correspondence with Karen Watte)
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: [email protected] or 541-357-2222.



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