Upon his father's death in 1788, Ravenscroft returned to Virginia to manage the family lands, as well as pursue their Loyalist indemnification claims. At age 27, he enrolled at the College of William & Mary to prepare for a legal career under the guidance of George Wythe and St. George Tucker. However, the wealthy young man also had extracurricular activities which, with his hot temper, earned him the nickname "Mad Jack". Eventually, he returned to Scotland to finish settling his father’s estate.