When John Wilkes Booth was cornered and killed at the Garrett farm, it marked the end of his escape and the southernmost point of his journey. However, the Garrett Farm was not the southernmost point for his co-conspirator David Herold, who accompanied him. After Booth was dropped off at the Garrett’s on the afternoon of April 24th, David Herold continued south with three Confederate soldiers, Willie Jett, Absalom Bainbridge and his cousin Mortimer Ruggles. About halfway before they reached the city of Bowling Green, the quartet stopped at the home of Mrs. Carter called, “The Trappe”. The Trappe was a tavern for passing visitors and also a house of entertainment. While at the Trappe, the men discussed where they would go from there.
Willie Jett had a girlfriend in nearby Bowling Green by the name of Izora Gouldman. Her family owned the Star Hotel in Bowling Green, and so Jett planned to ride there and spend the night with them. Bainbridge knew another family who lived outside of Bowling Green named the Clarkes. Bainbridge had served with James Clarke, the son of the owner, Virginia Clarke and he proposed to spend the night there. Davy Herold, remarkably, had also met James Clarke three or four years previously and decided to go with Bainbridge to the Clarke house for the night. Where Ruggles spent the night, either at the Star Hotel or Mrs. Clarke’s house, is unknown to this author. The men then split up and went to their prospective places of rest. The next morning, all the men regrouped at the Star Hotel before Davy decided to go and rejoin Booth at the Garrett farm. Ruggles and Bainbridge escorted him while Jett stayed behind in Bowling Green. That night, Willie Jett was still at the Star Hotel when the Union troops came looking for him. He was asleep and sharing a bed with Izora’s brother, Jesse Gouldman when the troops surrounded the hotel and forced Jett to reveal Booth’s whereabouts. With Jett arrested and acting as a guide, the cavalry travelled to the Garrett farm for Booth’s final performance.