Main has been an adjunct professor at Loyola University Chicago, teaching media law.
[2] Main won the 2011 Pulitzer Prize for Local Reporting with Mark Konkol and John Kim for articles documenting violence in Chicago neighborhoods and the culture of silence that allows it to continue.
[3] The entry included two series that examined the same issue: how many assault and murder cases in Chicago go unsolved because victims, witnesses and neighbors refuse to cooperate with police.
Main spent four months shadowing homicide detectives as they tried to solve the gang-related murder of a teenager only to be stymied by a "no-snitch" culture.
[4] In 2017, Main won the APME national storytelling award for 'Life on a Ledge,' which detailed a suicide he witnessed in Chicago.