The son of a Greek immigrant grocer, Kass was born June 23, 1956, on Chicago's South Side and grew up there and in Oak Lawn. He held a number of jobs — merchant marine sailor, ditch digger, waiter — before becoming a film student at Columbia College in Chicago, where he worked at the student newspaper. He obtained an internship at the Daily Calumet in 1980, and ended up working there as a reporter until he left for the Tribune in 1983. He has won honors including the Society of Professional Journalists' Sigma Delta Chi national award for general column writing, the Scripps Howard Foundation's National Journalism Award for commentary, the Chicago Headline Club's Lisagor Award for best daily newspaper columnist and the Chicago Tribune's Beck Award for writing. He lives in the western suburbs with his wife and twin sons.