Jonathan graduated cum laude from Princeton University, where he was national champion of the American Parliamentary Debate Association, and received his law degree summa cum laude from Harvard Law School, where he was an editor of the Harvard Law Review and winner of the First-Year and Second-Year Sears Prizes. After graduating law school, he served as law clerk to the Honorable Stephen Reinhardt of the United States Court of Appeals for the Ninth Circuit and the Honorable Elena Kagan of the Supreme Court of the United States.