Jonathan made aliyah from New York in 2003 and enlisted in the IDF, where he served as a combat officer. He currently holds the rank of Major in the reserves. Jonathan completed a bachelor's and master's degree in international relations from Hebrew University in Jerusalem. After working for Jerusalem Mayor Nir Barkat and Prime Minister Netanyahu, Jonathan made a career change to medicine. He is currently a medical student at Ben-Gurion University in the Negev.