[1] As a young boy growing up in Chicago, Simon was impacted by the politics of the 1960s, including anti-war protests and the assassination of Fred Hampton.
[3] Simon cites his academic interest in crime and punishment as stemming from his own experience being arrested for civil disobedience in 1981, and witnessing the demographics and treatment of the prisoners in jail in Alameda County, California.
[3] With Malcom Feeley, Simon published a theory of "new penology" in 1992 that placed early attention on what is sometimes called, "actuarial justice" or "risk assessment," which is primarily concerned with the correct identification, classification, and management of groups categorized according to perceived dangerousness and the logic of efficient administration.
[7] In 2014 Simon published his most recent monograph, Mass Incarceration on Trial: A Remarkable Court Decision and the Future of Prisons in America, in which he "examines the 2011 U.S. Supreme Court case Brown v. Plata as a lens into the country’s larger dependence on mass incarceration as a crime control policy" and explores the causes and consequences of prison overcrowding amid falling crime rates in the 1980s.
[8] As of 2022, Simon has published over 90 academic articles on subjects including crime, punishment, incarceration, eugenics, violence, the death penalty, and more.
He often contributes to news platforms and magazines such as the San Francisco Chronicle, the New York Times, the Atlantic, NPR, and more.