BackgroundLenny was born circa 1880. Both of his parents were former slaves. His father was an educated man who could read and write, and taught Lenny everything he knew. Lenny's father also gave him a pocketwatch, 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 afterwards, being only 15 years old at the time, and eventually joined the Van der Linde gang while traversing the Grizzlies in late 1898.
Events of Red Dead Redemption 2
Lenny takes part in the assault of the O'Driscoll camp in which he is paired up with Javier Escuella, 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 how he is always ready.
After the explosives that were supposed to bring the train down fail to work, Lenny, Javier and Arthur chase after the train and jump aboard. Although Javier falls off, Arthur and Lenny succeed and the two fight their way across the train. The two manage to eliminate most of the train guards themselves, before Dutch and the others arrive and neutralize the remaining few. Afterwards, Arthur, Lenny and Micah are sent inside to loot the private car, and Lenny is praised by the gang for his actions.
Horseshoe Overlook Chapter
When the gang are leaving the mountains, Lenny and Micah are sent scouting ahead and end up in the town of Strawberry. After Micah is arrested and sentenced to be hanged 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 Lenny to 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. The next morning, Lenny secures their release by paying their bail to a deputy.
Clemens Point Chapter
After wandering around in the town of Rhodes and speaking to the black community 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 named Shady Belle, and have many expensive weapons which they are selling to other countries. He convinces Arthur to go with him, and the two assault Shady Belle. 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 is the driver of the stagecoach that Arthur, Dutch, Hosea and Bill travel in when they attend the party at Mayor Lemieux's residence. When the four leave the party, Lenny drives them back to camp in the stagecoach.
Following a tip given to Dutch by Angelo Bronte at the party, Lenny, Arthur and Dutch rob the Saint Denis trolley station. However, the tip soon proves 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, and the trio is forced to shoot their way out of the city to escape. Lenny leads most of the escape and is later 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 setup, 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 setups.
Lenny is also involved in the assault 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 riflemen while leading the gang's 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.
Later on, Sadie mentions 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 Lenny and Hosea (who also died during the robbery) together in the Bluewater Marsh.
Lenny is shown to be an intelligent, fun-loving young man. He is also shown to be very competent and effective in many situations, with Hosea and Arthur particularly viewing him as one of the gang's best men. Like most members, he is very loyal to the Van der Linde gang and considers them family. 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 confident and cocky attitude; he replies with "’course I’m ready" when Javier asks if he’s ready for the train robbery, and isn’t afraid to get his hands dirty on many occasions. He even leads most of the escape during the Saint Denis trolley station robbery, and later in the bank robbery, showing his confidence. When playing Poker and Five Finger Fillet at camp he will playfully 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 neat, relatively short black hair. He has little in the way of facial hair and is often seen wearing a buttoned white shirt and braces, 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.
- Red Dead Redemption 2
- "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 buried 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.
- 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.
- ↑ During the stagecoach robbery with Lenny, Arthur states that Lenny has been with the gang for six months.