I live in Chicago and pass by the IWW world headquarters each day, but it's a very small storefront and office, and I know it used to be a much more prominent organization. My grandfather was a sailor, a member of the IWW, and a very vocal socialist. He had an IWW songbook, and I recognize some of the songs from Woodie Guthrie and Pete Seeger.
I can help a bit on this one. The Wobblies were the radical edge of the union movement. Some unions aspired to get better conditions for their workers, or simply prevent them from being abused. In the periodic "panics" or economic depressions of the later 1800's, workers were often the easiest target when businesses were cutting costs, and conservative unions like the AFL simply wanted to keep their wages from being constantly reduced. The IWW wanted to remake society, embracing socialism, and tried to enroll not only factory workers but even migrant laborers. It also was willing to resort to sabotaging equipment and getting workers to slow down their pace, instead of having direct and open negotiations and strikes. It was therefore regarded by business interests ( which typically would be not only businesses in a state but the governor of the state as well) as far more threatening. But as its societal goals were far deeper and wider than unions like the AFL, its rhetoric was loftier.
It was therefore just the kind of place for an idealistic poet, and it got one in Joe Hill. ( Joel Haaglund) 1879-1915. He tramped around the US after arriving in 1902, agitating and writing many songs and poems. In 1915 the State of Utah took the opportunity to convict him of murdering two men in a robbery, and made him into a martyr for the labor movement. His words in a final letter to IWW leader Bill Haywood "don't mourn- organize!" have continued to be used. His execution inspired many good songs ( like Edward Robinson's Joe Hill) and many of his own songs continued to be sung, like The Tramp.
The University of Utah did a nice documentary on Hill here. William Adler did a new biography of him , The Man Who Never Died, that has more information on precisely how Hill came to have a gunshot wound when police picked him up in 1915.