BackgroundLenny was presumably born sometime in the late 1870s to early 1880s. 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 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 watch in Blackwater.
Events of Red Dead Redemption 2
Although Lenny took part in the assault of the O'Driscoll camp, he first takes the spotlight when the gang is robbing the Cornwall Company Train. Before the robbery, Dutch praises Lenny for his eagerness, and always being ready. After the explosives don't go off that were supposed to bring the train down, Lenny and Arthur jump aboard it. The two fight their way across the train before Lenny is ambushed by the engineer. Arthur slays the engineer, and they stop the train. Afterward, Lenny is praised by the gang.
Horseshoe Overlook Chapter
Not long after moving to the Valentine area, Lenny and Micah go wandering over to the town of Strawberry. After Micah is captured for murdering an O'Driscoll gang member, Lenny runs back to the gang and tells them what happened. Dutch tells Arthur to take him to the Smithfield's Saloon to calm his nerves, where the two get very drunk. They later get chased by the deputies in the town for their drunkenness. However, Lenny is caught by a deputy. If Arthur failed to evade the deputies, he and Lenny will be seen in a jail cell. Lenny will pay their bail to a deputy.
Clemens Point Chapter
After wandering around in the town of Rhodes and speaking to the colored folk there, he learns of a group of ex-confederates known as the Lemoyne Raiders. He learns that this gang is camped in an old plantation house, and have many expensive weapons which they are selling to other countries. He convinces Arthur to go with him, and the two assault the plantation. After killing the Lemoyne Raiders occupying the plantation, they take a bunch of weapons and ride off. The pair is ambushed after fleeing the place, but they fight themselves free. Immediately afterward, Bill approaches them, and they along with Karen rob the bank. Lawmen quickly close in, but the four gang members fight their way out, taking with them several thousand dollars. Lenny later takes part in the assault against Braithwaite manor.
Shady Belle Chapter
Lenny, along with Arthur and Dutch, goes and robs the Saint-Denis trolley station, after receiving a tip from Angelo Bronte. The tip soon proved to be a setup, as the station's vault contained only ninety dollars. Lawmen then descended upon them, and they were forced to ride an empty trolley out of the city.
During the Saint-Denis bank robbery, Lenny is unceremoniously gunned down by two Pinkerton agents during their escape on the rooftops. After quickly killing the Pinkertons, Arthur kneels down next to Lenny to briefly mourn his death before being forced to flee.
Sadie Adler mentions later on that she and the remaining gang managed to get Lenny's body out of Saint-Denis by robbing the local morgue, and eventually buried both Hosea and Lenny together in the Bluewater Marsh.
Lenny is extremely eager, and always happy to help the gang, whom he considers his family.
- "Outlaws from the West"
- "Old Friends"
- "Who the Hell is Leviticus Cornwall?"
- "Eastward Bound"
- "A Quiet Time"
- "Preaching Forgiveness as He Went"
- "Sodom? Back to Gomorrah"
- "Blood Feuds, Ancient and Modern"
- "The Battle of Shady Belle"
- "The Gilded Cage"
- "Urban Pleasures"
- "Revenge is a Dish Best Eaten"
- "Banking, The Old American Art"
- After his death, he is buried next to Hosea. They can be visited after the mission "Fleeting Joy" in Chapter 5.