The Boss Saloon: A Den of Scullduggery. (1870s-1940s)

The Boss Saloon in later, less scandalous times.
Before the Willamette was bridged, river crossing was via ferry. One such ferry, beginning around 1870, ran from Flanders St. on the west bank to a spot where the current Steel Bridge makes landfall on the east bank.¹ On the west side, between Davis & Flanders, stood a 2-story waiting room building of the "flatiron" design: triangular w/ 3 sides.

In 1888, when ferry service ended after the 1st Steel Bridge was completed, the building became a saloon, moonlighting as a hiring hall for sailors to serve the grain ships which docked nearby. Not suprisingly, it was also, purportedly, a hotbed for shanghai-ing.²


Portland harbor in 1906.
According to legend, the Portland Merchants Exchange was birthed at the Boss.

a bartender, tired of answering questions, put up a blackboard behind his bar to list incoming ships and their berths for the information of sailors and waterfront gentry.

The exchange was organized and incorporated in 1879, the same year the O&CRR Ferry No. 2 was launched, and moved "uptown" to First and Ankeny streets.³

In later years the saloon became a simple eatery, "Boss Lunch."

I'm sure it was demolished no later than the 1940s to make way for Harbor Drive (subsequently transformed into Waterfront Park).

-d.d.



¹ This ferry was essentially a shuttle service to the terminal of Henry Villard's (& subsequently Ben Holladay's) Oregon & California RR, which also owned the ferry. Holladay would later build Portland's 1st horse-drawn steetcar line to shuttle RR/ferry passengers south into "downtown" Portland.
² Perhaps more of a nerve center for Portland's shanghai system. Famous crimper Jim Turk used it as a base. Turk, reportedly, shanghai-ed his own son!! By the Willie Week (great article, btw), Turk is buried

Close by the corner of 20th and Morrison one finds the grave of hard-drinking Jim Turk, one of Portland's most infamous shanghai specialists, who sent many a drunk and unconscious lumberman to sea via the mildewed tunnels beneath Old Town; in death, Turk masquerades as little more than a wealthy pillar of local industry.

Further tales of Turk & fellow crimpers Larry Sullivan & Jim 'Bunco' Kelly include Kelly (who crimped 50 men in 3 hours, once) discovering 20 dead men who

had apparently found a keg in the cellar of a saloon and drunk heartily. It turned out, however, that they were actually in the mortuary next door and had drunk embalming fluid (formaldehyde) instead! Not a man to waste an opportunity, Kelly sold the bodies to an unsuspecting captain for $52 each ($2.00 over the going rate) because he had managed to get the men so “dead drunk” that they surely wouldn’t awaken until well out at sea.

Of course, if your are familiar w/ Portland in the end of the 1800s none of this should come as a surprise. Still, you should read this comic.
³ You can read about the Boss, & mainly abt what became of the 2nd ferry for which people awaited at the Boss, here.