Green’s Dictionary of Slang

(Aus./US) derog. term for a member of the Industrial Workers of the World (IWW).

1909		Seattle Star (WA) 3 Nov. 4/1: In Spokane at present I.W.W. stands for I Won’t Work.
1913		Voice of the People (New Orleans) 2/2: What is the I.W.W.? ‘I won’t work!’ - they answer in chorus.
1918		R.H. Knyvett ‘Over There’ with the Australians 260: On Saturdays I felt it might be a Jew or a Seventh-Day Adventist, but then it [i.e. a paralysed leg] did not work on other days either, so I thought it must be I. W. W., ‘I Won’t Work’ as they are called in Australia.
1923		N. Anderson Hobo 235: The I.W.W. is little understood by society in general. The public believes it is an organization of ‘tramps who won’t work,’ and that the initials stand for ‘I Won’t Work,’ or ‘I Want Whiskey’.
1930		(con. 1900s–10s) Dos Passos 42nd Parallel in USA (1966) 325: The boss said he’d have no goddam I Won’t Works in this outfit.