Lenny was born circa 1880. Both of his parents were former slaves. His father was an educated man that knew how to read and write and taught Lenny everything he knew. Lenny's father also gave him a pocket watch, which his former owner gave to him. One fateful night, his father was beaten to death by a few drunk men, whom Lenny killed in revenge. He was forced to go on the run afterward, being only 15 at the time, and later joined the Van der Linde gang sometime before the failed Blackwater Ferry Robbery. It is known that he fell in love with Jenny Kirk sometime before her death, and her loss hit him hard. Lenny also lost his father's pocket watch in Blackwater.