Levi Hollingsworth, younger brother of Zebulon Hollingsworth Jr., was born on 29 November 1739 in Head of Elk (present-day Elkton), Maryland. As a young man he moved to Philadelphia, where he became a successful merchant. A pre-Revolutionary War volunteer for Philadelphia cavalry, Hollingsworth fought in the battles of Trenton and Princeton. He later became a leader of the Federalist party in Philadelphia while continuing his mercantile career. Hollingsworth and wife Hannah Paschall (1744–1833, m.