Since Portland’s earliest days, the neighborhood now known as Old Town has been the place for the transient, the homeless and the unwanted. Portland’s most racially mixed neighborhood before 1919, the North End was the home to Chinese, Japanese, African-American, Gypsy and other immigrant Portlanders. Oregon’s economy was built on migrant labor, and the city’s population often tripled during the rainy season. The migrant workers, many of them flush with cash, joined the ethnic stew of the North End.

Following the anti-vice campaigns of the 1880s illegal vice activities – gambling, prostitution and drug use – were confined more and more in the North End. The police force’s policy of containment created a kind of “free crime zone,” and the North End became a dangerous neighborhood. The combination of diverse ethnicity, a transient population and rampant criminal activity made the North End ripe for political organizing. One of the most successful and interesting examples of organizing in the North End was the Industrial Workers of the World (IWW), or Wobblies.

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The early 20th century was a time of radical ideas as Americans began to learn how to govern themselves. The IWW, born out of the bloody struggle between the Western Federation of Miners and the Rocky Mountain mine operators, was the first embodiment of an industrial union – in which workers throughout an industry bargained together, regardless of their job. The IWW, devoted to the General Strike – in which the workers would seize control of the means of production, excising capital from the system – was committed to equal rights and focused their organizing on workers excluded from traditional unions: women, non-white workers, young workers and the unemployed.

The Portland branch of the IWW organized in 1907 during the strike at the Eastern and Western Lumber Mill. The first IWW office was located on West Burnside Street near Second Avenue, but it soon relocated to Northwest Second and Couch and then to Northwest Davis Street, where it remained for many years. The IWW was subject to harassment by the police and by vigilantes, and its office was wrecked several times.

The Portland branch of IWW got its first national recognition during its annual convention of 1908. The big question that year was whether the IWW would endorse political candidates or focus only on union organizing. The Portland branch, with many talented musicians such as J.H. Walsh, Pat Kelly and Harry “Haywire Mac” McClintock as members, sent a singing delegation, known as the Overalls Brigade, to campaign for organizing over political action. The Overalls Brigade, dressed in black shirts and overalls with bright red bowties, walked and rode the rails to Chicago where they used songs, such as Pat Kelly’s “Hallelujah, I’m a Bum” to rally the forces for organizing. After the 1908 convention, the IWW rejected political action as a tactic, concentrating on organizing instead.

Cultural resistance, making use of popular forms of expression like graphic design, cartoons and songs, was one of the Wobblies’ most effective tools. The Industrial Worker, the IWW newspaper sold for many years on the streets of Portland, gained great popularity mostly through the strength of Mr. Block, their comic strip anti-hero. Portland’s biggest contribution to this cultural resistance was in song. “The Little Red Songbook,” carried like a bible by union organizers all over the world, was born in the North End office of the IWW in Portland.

“The Little Red Songbook,” still printed and used today, was first published in Spokane, Wash., in 1909, but most of the original songs came from Portland Wobblies, many of whom were members of the Overalls Brigade. When Joe Hill, the famous Wobbly songwriter and martyr (killed by the state of Utah in 1915), wanted to have his song “The Preacher and the Slave” included in the collection, he came to Portland to audition. His song, which coined the phrase “pie in the sky,” was first performed for an audience in Lownsdale Square in November 1910.

One of the IWW’s most visible tactics was the Free Speech Fight, a campaign of civil disobedience where Wobblies converged on a city to challenge bans on street speaking with the goal of “filling the jails.” The IWW staged Free Speech Fights in every major city in the West, becoming famous for oratory by such talented speakers as Helen Gurley Flynn and Big Bill Haywood.

Portland’s Free Speech Fight occurred in 1913 during the Oregon Packing Company strike. The Oregon Packing Company, at Southeast Seventh and Belmont streets, employed mainly women workers. Women in the fruit cannery worked 10- to 12-hour days. Working for a “piece rate,” most workers in the factory earned less than a dollar a day and worked under horrible conditions. For example, in an effort to keep union organizers out of the plant, the employer chained the doors closed, forcing temperatures inside over 100 degrees.

In an effort to call attention to the struggle of the Oregon Packing Co. workers, the union staged marches across the Morrison Bridge at rush hour. The marches would usually end near the corner of Southwest Sixth and Washington Street with large rallies and many street speakers. The location was chosen, although Lownsdale Square was the traditional location for political speec, because of the large crowds of working people who would gather there on their way home from work.

The newly elected mayor, Russell Albee, was a supporter of craft unionism and sympathetic to the striking workers, but in an attempt to be “impartial,” he ordered Multnomah County Sheriff Tom Word to take a hard line with the demonstrators.

July 1913 saw bloody street battles as speaker after speaker was dragged from the soapbox, beaten and arrested. The events of that summer are credited with radicalizing two of Portland’s most important political activists: Dr. Marie Equi and Tom Burns.

Equi, whose practice specialized in women’s health, was the doctor of many striking workers from Oregon Packing. Angered by the treatment the striking women received from the police, Equi joined the street speakers and was arrested herself. Equi, Portland’s first well-known lesbian, protested passionately and eloquently against the brutality of the police, beginning her career as a political activist that eventually led to her serious injury at the hands of the police and a prison sentence for speaking against the Great War.

Burns, a clock maker and son of a British member of Parliament, came to Portland in 1905. During the Oregon Packing Co. strike of 1913, Burns was one of the first street speakers pulled from his soapbox and beaten after proclaiming, “We will fly the red flag of anarchy over the marble palace up there,” while gesturing toward City Hall. Burns, who died in 1957, remained politically active for the rest of his life, earning the titles of “Mayor of Burnside” and “Portland’s Most Arrested Man.” His Clock Shop, at 221 W Burnside, had a radical lending library in the basement and took the place of the old Wobbly Hall as the gathering place for radicals in Portland.

With support from Equi; C.E.S. Wood, Portland’s most important literary figure at the time; and John Reed, a Portlander who became an internationally famous journalist with his reporting of the Russian Revolution, the IWW became socially popular. Many of Portland’s literary and art community came to support the IWW’s radical cause. Wobbly Hall on Northwest Davis became a popular gathering place for radicals, and those who flirted with their ideas. Political speakers from around the world found an audience there while Portland socialites rubbed elbows with the down and out.

Between 1900 and 1919, Portland experienced a great surge of progressive politics and support for labor unions, culminating in Will Daly’s campaign for mayor in 1917. Wobbly Hall in the North End was an important part of that surge, and the Wobblies were the main target of the police and other forces of oppression. In 1913, Police Chief Enoch Slover tried unsuccessfully to convict IWW organizer Gordon Napier for the murder of John A. Brown at the Elkhorn Café, near Wobbly Hall. Although the murder case fell apart quickly and the investigation into the killing was dropped, the Wobblies were smeared with a reputation for violence. The truth was that most Wobblies were committed to non-violence and were usually victims themselves.

Although the Elkhorn murder case may have been legally worthless, the propaganda value was enormous. The Greek Scandal, which followed the next month, in which young gay men and trans women were arrested at the Monte Carlo Poolroom and Fairmont Hotel in the North End, was an attempt to smear immigrant working-class men with the label “homosexual.” Police propaganda campaigns couldn’t hurt the IWW’s popularity among the working class, but they successfully eroded their popular appeal among artists and society members. More and more, the radical IWW was isolated from the mainstream progressive community.

The IWW gained its greatest strength in the lumber camps of Oregon and Washington, where they fought for the eight-hour day and better living conditions. By 1917, the lumber industry in the Pacific Northwest was nearly paralyzed, especially the vital production of spruce needed to build both ships and planes for the Great War. The U.S. Army seized control of the lumber industry, giving in to the striker’s demands, but outlawing the IWW. By the time of the 1919 Centralia Massacre, in which Wobblies were lynched for defending their union hall from violent American Legion vigilantes, the union was in serious decline with most of its leaders dead, in prison or in exile.

In Portland, most Wobblies went underground, joining other unions, such as the sailors union and the longshoremen’s union. Their ideals gained popularity with the labor organizing of the 1930s, and IWW tactics and theories became very important in the industrial unions of the Congress of Industrial Organizations, or CIO. In the 1990s, the IWW was reborn as a union, and it has been building its strength in Portland ever since, continuing the work of organizing those excluded from traditional unions.

JD Chandler is a Portland historian and the author of “Hidden History of Portland.” (History Press)