During law school, Jonathan served as an intern in the U.S. Attorney's Office for the Eastern District of New York, where he conducted legal research and prepared legal memoranda for the attorneys in both the General Crimes and Organized Crime and Gangs divisions. He was also a clinic student at the U.S. Senate Committee on Foreign Relations and at the Brennan Center for Justice.
Prior to law school, Jonathan was awarded a Fulbright Scholarship and spent a year as an English teaching assistant in Cao Bằng, Vietnam, and served as an intern in the Juvenile Division of the Office of the Public Defender.