Through Walter F. Starbuck and near-rambling biographical sketches of the various characters referenced in the novel, Jailbird concerns itself with the history of the American labor movement, while also pointing out flaws in corporate America, the American political system, the American red scare of the late 1950's, and both capitalist and communist theory.
Jailbird also features a brief appearance of Kilgore Trout, a recurring Vonnegut character who writes science fiction novellas.