Lenny was born in 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 some time before her death, and her loss hit him hard. Lenny also lost his father's watch in Blackwater.
Events of Red Dead Redemption 2
Lenny takes part in the assault of the O'Driscoll camp, although 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 chase after the train and 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 are sent scouting ahead, and end up in the town of Strawberry. After Micah is arrested for murdering two O'Driscolls in a bar fight, 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. The law will also chase after Arthur, who can escape. If Arthur failed to evade the deputies, however, 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 the stash of weapons and ride off. The pair are ambushed after fleeing the place, but they fight off their attackers and bring the weapons back to camp.
Soon afterwards, Bill approaches Lenny and Arthur, along with Karen, to rob the bank in Valentine. The robbery is successful and, although Lawmen begin to close in, the four gang members manage to fight their way out and escape the law, taking with them several thousand dollars. Lenny later takes part in the assault against the Braithwaite Manor.
Saint Denis Chapter
Lenny, along with Arthur and Dutch, rob 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. Numerous officers from the Saint Denis Police Department then descend upon them. The trio is forced to shoot their way out of the city to escape. Lenny is once again praised for his competency.
Arthur can also rob a stagecoach with Lenny in this chapter; Lenny originally wishes to go alone after finding a lead, but Arthur insists that he should go too. The robbery turns out to be a set up, however, although the pair do manage to complete the robbery. Afterwards, Arthur warns Lenny to be careful of leads that come from the stagecoach company, as they are often used as set ups.
Lenny is also involved in the attack on Angelo Bronte's mansion, and helps fight off the police so that the gang can kidnap Bronte.
Soon afterwards, during the Saint-Denis bank robbery, Lenny is gunned down and killed 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 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 (who also died during the robbery) and Lenny together in the Bluewater Marsh.
Lenny is shown to be an intelligent, fun-loving young man. Like most members, he is very loyal to the Van der Linde gang and considers them family. Although showing signs of fear at the beginning of the game, after he and Arthur get drunk in Valentine his demeanor becomes more confident and determined. Out of everyone at camp, he appears to be the sanest; perhaps the second most insightful to Hosea. This is likely due to his upbringing which, when compared to others in the gang, was more reasonably decent.
He shows a cocky attitude when playing Poker and Five Finger Fillet at camp, and will tease Arthur about being slow due to his older age.
Despite being part of an ethnic minority he displays no real care of what others think, likely because the gang as a whole live an outcast lifestyle and are all minorities themselves in various ways. He sometimes satirically compares himself to common black stereotypes. In a conversation with Sean MacGuire, Lenny states he's uncertain of who to hate more; the slavers who oppressed his ancestors, or the general white populace for antagonizing him because of the recent Emancipation Proclamation.
Lenny has black skin and short, neat hair. He has little in the way of facial hair, and is often seen wearing a white shirt with braces, where the buttons of the shirt are usually undone at the top, accompanied with black trousers. Lenny is a young, nineteen year old man at the time of the Red Dead Redemption 2, and is seen to be of a fairly slim build, and slightly shorter than Arthur. In cold temperatures, Lenny is seen wearing a blue coat with a stripy scarf and grey trousers.
- "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."
- Ironically, both Lenny and Hosea stated in a random dialogue that they wanted to be burried with friends, foreshadowing that they would be buried together.
- Hosea and Lenny's relationship mirrors Arthur and John's. Both relationships feature one member (Hosea and Arthur) being unsure about their more junior comrade (Lenny and John), but later grow to like them and eventually try to convince the other member to leave the gang, however Lenny remains loyal to the gang until death, where as John leaves to start a better life for his family.
- It's apparent that Lenny had a crush on Jenny Kirk from the game's dialogue. He brings up the idea of giving her a proper burial in Colter, mentions her when playing Five Finger Fillet and Arthur and Hosea discuss his fondness of her.
- Whilst at Horseshoe Overlook, he can be seen debating with Dutch over Evelyn Miller and his books. Lenny argues that the author is a fraud; that their gang is a better representation of American freedom than Miller's ideas, which causes Dutch to laugh and concede the argument.
- His primary weapon of choice appears to be a custom Cattleman Revolver with a black steel frame and an ebony grip.
- Lenny is the only member of the gang who dies outside of a cutscene.
- There is a letter at camp titled 'Letter to Lenny from Father'. In it, the writer mentions his own abandonment of his family, that he had been 'more tutor than father' and that he hoped his son's future was as a lawyer. It also states "you have redeemed more than you know, or can ever know, or should ever be expected to bear", tying in with the series' theme of redemption.