Lenny accompanied Wade (who had a lot of reservations about letting him tag along) during the kidnapping of Victoria from the Rosewood Orphanage, during which he accidentally killed Sister Mary. After Wade was eliminated by 47, Lenny kidnapped Victoria and brought her back to his hometown of Hope, South Dakota, for his father.
Following these events, 47 tracked down Lenny and his gang members. Once the rest of the Cougars had been dealt with, 47 kidnapped Lenny and forced him to dig a grave in the middle of a barren desert, whilst questioning him on the location of Victoria. Once Lenny tells 47 of Victoria's location, the player is given the choice of killing Lenny (either by shooting him, attacking him in close combat, or the explosives he hides behind) or letting him live at the mercy of vultures, presumably to die from dehydration. Either way, Lenny doesn't reappear in the game.
- He walks with a limp. Hence the name "Limp Dick Lenny". Actual erectile dysfunction is unconfirmed.
- He is the leader of the Hope Cougars, a small-time gang in the town of Hope, South Dakota.
- Has a couple of tattoos on both arms and one on his lower back.
- He may be bisexual; in the End of the Road mission, he'll offer to give 47 "a real good reach-around" in exchange for sparing his life, though this could just be out of desperation. He also has a bunch of books in his room in Blackwater Park with titles like "How To Meet Girls."
- Despite having come face to face with 47 once earlier, he will not recognize him if he is in a barber disguise, even with his face visible. He will even comment what happened in Rosewood Orphanage while he can see 47 through the mirror.
- However, if 47's cover is blown, he will comment about 47.
- Lenny and his Hope Cougars gang are disliked by most people in Hope, South Dakota. You can listen to NPCs comment on Lenny before you meet him.
- If the player decides to leave Lenny alive in the desert, Lenny will continue to speak during the 'Lost and Found' menu, stating that he was once a cub scout, along with miscellaneous dialogue.
- The End of the road mission where 47 kills Lenny, might be a reference to the book Of Mice and Men where a character Lennie is shot by George after he is hunted for a crime.
- If the player lets Lenny limp to the derelict explosives wagon without doing anything; he will suddenly take cover behind the wagon, turn hostile and shoot at 47 with his derringer pistol, all the while mocking him with several insults. Lenny has no spare ammunition, is incredibly inaccurate, and has very low possibility to kill 47 even with two direct hits should even be fortunate enough to do that. He will then return to his cowardly state after running out of ammo and walking near him, justifying his assault because 47 killed his friends and he thought he was going to attack him.
- If the player shoots the five vultures (while they are in the air) in End of the Road, Lenny will walk closer to 47 and stand in the middle of the road, where he will be hit and killed by a speeding ice cream truck.
- In Blackwater Park, his bedroom contains half-eaten Pop Tarts, a guide titled "Get the Girls You Want," a bong, and a sniper rifle with a nearby tally of how many pigeons he's shot.
- In the leaderboard of McGarmond's Gun Shop, you can see his name on the contest scoreboard. He apparently used a Swiss Derringer (which you can find on his corpse in End of the Road) and scored 129, significantly lower than all but one other contestants.
- Apparently, Lenny was a cub scout in his youth, according to the bonus dialouge after End of the Road. Within the same bonus dialouge, it's revealed that 47, strangely, left Lenny's phone with him as he tries to call for his gang members, though this might be due to 47 not wanting to waste any more time on Lenny.