In the late 1940s, Golub met the artist Nancy Spero (1926 – 2009) to whom he was married, and collaborated with variously, for nearly 50 years. During this time, Golub became involved with the Monster Roster Group: a post-war circle of artists based in Chicago and united by a shared fascination with surrealism, mythology and ancient art, systems of representation, and the politics of social critique. This early engagement, especially for its motion away from then dominant abstract modes of painting, informed the rest of Golub's career.
In 1950, Golub co-founded the event, ‘Exhibition Momentum,’ a confrontational response to the Art Institute of Chicago's banning of undergraduate submissions to its annual ‘Artists of Chicago and Vicinity’ exhibition. This recalcitrant form of activism proved typical for Golub, remaining a constant facet of his artistic career and personal life. Indeed, Golub was often called upon to lend his voice to political causes and artistic debate.
In the 1970s and 1980s, the subject matter of Golub's work pivots as his attention increasingly turned to diverse manifestations of terrorism: from the subversive operations of governments to urban street violence and corrupt dynamics of power. References to interrogations, war, torture and mortality repeatedly surface in these later works, as Golub tackles themes of violent aggression, racial inequality, gender ambiguity, marginalization, oppression and exclusion.
From the 1990s until his death, Golub experimented with a greater illusionism: often appropriating graphic styles from ancient carvings, medieval manuscripts and contemporary graffiti.