Steven Dudley was born in 1969 in St. Louis, Missouri, and grew up in Oak Park, Illinois, a place another Oak Park-native, Ernest Hemingway, once remarked had "broad lawns and narrow minds." By the time Dudley was growing up, the Republicans had been replaced by Chicago-based mobsters. One of them, Sam "Mooney" Giancana, had a house on the south side, the same place where he was assassinated in 1975. The area's "Big Tuna," Anthony Accardo, had a house in the town next door. Dudley's brothers played football with Accardo's grandchildren; Accardo attended the games wearing a fur coat with bodyguards in tow.

Dudley attended Cornell University, far from the Chicago Mafia, where he studied Latin American history. His fascination with evil governments and mobsters eventually led him to Guatemala and later Colombia where he worked in Human Rights. After doing a Master's in Latin American Studies at the University of Texas, Austin, he returned to Colombia where he reported for the Washington Post, the Economist, National Public Radio, the BBC and others, and wrote a book, Walking Ghosts: Murder and Guerrilla Politics in Colombia (Routledge: 2004) on Colombia's war. He later served as the Miami Herald's Bureau Chief in the Andes, and in 2010, he co-founded InSight Crime, a think tank that investigates organized crime in the Americas.

He currently lives in Washington DC where he is co-director of InSight Crime and a fellow at American University's Center for Latin American and Latino Studies. He was a Knight Fellow at Stanford University (2007-2008) and a fellow at the Woodrow Wilson Center in Washington DC (2012-2013). He is also a member of the International Consortium of Investigative Journalists, and in 2019 he won the Lucas Prize for work-in-progress for his forthcoming book, MS-13: The Making of the World's Most Notorious Gang