The Industrial Workers of the World (IWW), or Wobblies, originated in Chicago in 1905 as a loose amalgam of labor and political entities, principally the Western Federation of Miners (WFM) and various socialist political parties. The union aspired to organize all workers by industry (hence the name "Industrial") instead of by skill categories, as did trade unions like the American Federation of Labor. Led by "Big Bill" Haywood from the WFM, the Wobblies moved from organizing eastern factories full of unskilled immigrants and women in the early years to organizing the huge migrant labor force in the western United States that worked in the extractive industries of lumbering, mining and petroleum, and agriculture. Immigrant, homeless, relying on the railroads for transportation, and camping on the edges of towns in so-called jungles, the migrant worker was the ultimate invisible person. The Wobblies created an organization that enlisted migrant workers as the foot soldiers in their "army of the revolution."

The IWW did not see itself as a political party and eschewed involvement with any political system. Rather, it favored "direct action"–the use of labor action to solve labor problems. Rich in symbolism, and using a variety of visual images to present its story to a largely immigrant and often illiterate audience, the Wobblies became identified by the black cat and the French wooden shoe (sabot), the symbol for sabotage. Although the Wobbly newspaper hinted broadly at the advantages of sabotage for realizing goals, it is not clear to what extent sabotage was actually practiced.

In the Great Plains, the Wobblies reached their greatest extent and impact just prior to the World War I with a concerted effort to organize migrant wheat harvesters, the socalled bindlestiffs. They used a "contagion" method of organizing, where any new member could sign up additional new members. Capitalizing on the fact that railroads were really the only means of long-distance transportation, Wobblies took control of boxcars, organizing everyone in the car as the freight trains moved from town to town. Small-town sheriffs had no idea what to do when boxcar after boxcar loaded with singing, shouting Wobblies landed in their town. If they arrested one or two for disturbing the peace, the rest of the union would surround the jail and demand release. Employers were unaccustomed to having migrant workers band together to demand higher pay.

Between 1915 and 1917 the IWW swept across the Plains like a prairie fire. By the summer of 1916 the IWW was collecting dues from more than 18,000 migrant harvesters, and its organizers boasted of an "800-mile picket line" from Oklahoma to South Dakota. The Wobblies' mobility, developed from many years of practice as migrants, allowed them to appear to be everywhere at once.

After the onset of World War I, the image of the saboteur was used effectively against the union by state and federal agencies. When the Wobblies attempted to capture, in the form of increased wages, some of the money being fed into wartime industry, they were accused of sympathizing with Germany. Following the success of the Russian Revolution in 1917, the "army of the revolution" was dealt a serious blow by a series of coordinated government raids on IWW headquarters across the United States in September of that year. Hundreds of iww leaders were arrested and tried for treason and other charges, draining the union's coffers. Wichita, Kansas, became infamous for its rotating jail cells, in which at least one Wobbly died and many more wasted away waiting for trial. Big Bill Haywood emigrated to communist Russia following the war.

Ultimately, the advent of combine wheat harvesters obviated the need for huge numbers of migrant laborers, and the adoption of the automobile split migrants into small groups that could not be organized as effectively as entire boxcar loads. By the late 1920s the I Won't Works, as the Wobblies were nicknamed, were little more than an exciting memory in the Great Plains.