The paper's contents were a mix of radical politics, alternative lifestyles, and the counterculture, reflecting in part Marcuse's Frankfurt School Marxist/Freudian ideas of cultural transformation.
Break-ins, vandalism, and the fire-bombing of a car owned by the commune were allegedly carried out by paramilitary vigilantes calling themselves the Secret Army Organization (SAO).
Street vendors were arrested and the paper's editorial offices were broken into and robbed; in a break-in on Christmas Day 1969, a $4000 typesetting machine was thoroughly wrecked.
Several weeks later a fund-raising cocktail party to raise funds for the Street Journal was raided by police, who arrested Diepersloot for selling alcohol without a license.
On June 4, 2012 a group, associated with the OB Rag, including former contributors to the original San Diego Free Press/Street Journal, started SanDiegoFreePress.org as a website featuring neighborhood news and progressive viewpoints.