The fifth freedom seeker known to have been held in the Old Jail was a man named Tom, who had escaped from Dr. Henry A. Ford of Leonardtown. Contemporary records described him as approximately 34 years old, six feet tall, and well built, weighing around 160 pounds, with a distinctive imperfect thumb on his right hand. Also arrested in St. Mary’s County was Randolf Taylor, a free Black man standing about five feet ten inches tall and similarly built. Randolf told authorities he had come with the military and was originally from Maine.

In 1864, both men were charged with stealing a horse and cart from the estate of the late George C. Morgan, as well as with “enticing away” an enslaved woman and her children from that same estate — language that reveals how the law criminalized the act of helping people escape bondage. On the night of Sunday, January 28, 1864, the St. Mary’s Gazette reported that both men had escaped from the jail.

As in the case of the freedom seeker named John, Sheriff Philip H. Dorsey played a direct role in the pursuit. He publicly offered a $25 reward for the capture and return of both men, or $12.50 for either one — a reminder of how local law enforcement actively worked to enforce the slave system even as the Civil War was reshaping the nation around them.