Howard grew up in Port Jefferson, New York, the son of a French librarian mother and American philosopher father. As a child, Howard spent summers in Normandy with his grandparents and is a native speaker of both English and French. In 1993, Howard graduated from Yale University with a B.A. in Ethics, Politics, and Economics. He received two degrees in Political Science from the University of California, Berkeley, an M.A. in 1995 and a Ph.D. in 1999. While a student, he lived and researched in Germany for several years and in Russia for nearly one year, and he is fluent in German and Russian. Howard briefly taught at the University of California, Santa Cruz and at the University of Maryland, College Park from 2000 to 2003. Since 2003, Howard has been a professor in Georgetown's Department of Government. He received a J.D. in 2012 and a courtesy appointment as Professor of Law in 2014 from the Georgetown University Law Center. In 2016, Howard founded the Georgetown University Prisons and Justice Initiative, which brings together scholars, practitioners, and students to study the problem of mass incarceration. He is the author of the book, The Weakness of Civil Society in Post-Communist Europe. He also wrote The Politics of Citizenship in Europe, in 2009. Howard is the author of the forthcoming book Unusually Cruel: Prisons, Punishment, and the Real American Exceptionalism, which will be published by Oxford University Press in 2017.
Howard is a prominent supporter of criminal justice and prison reform in the United States. He became involved in prison reform through the case of his high school classmate, Marty Tankleff. In 1988, at age 17, Tankleff falsely confessed and was convicted of murdering his parents. Howard visited Tankleff in 2004 and began helping him win his release. In 2007, after 17 years in prison, Tankleff was exonerated and released when an appellate court overturned his conviction. Howard started teaching a course called "Prisons and Punishment" at Georgetown in 2011. The course featured a tour of the Jessup Correctional Institution, a maximum-security prison in Maryland, as well as a meeting and conversation with a group of "lifers" at Jessup. In 2014, Howard began teaching a full course to inmates at Jessup as part of the JCI Scholars Program.