- "You see the rules of the hunt don't mean jack out here. Now that rabbit you're holdin' is claimed, boy. Claimed whether you like it or not. So if I was you, I'd hand it over, now, before you get to wish you didn't even get out of bed this morning. You know, I bet there's a bitch, got you all messed up, am I right? Got you walking around here like a dead man, you just lost yourself a piece of tail, must've been a good'un'. Tell me something, was it one of the little'uns? 'Cause they... don't last too long out here."
- —Len to Daryl Dixon while they're hunting[src]
Nothing is known about Len's life before or as the outbreak began. It is implied, before his death, that before the outbreak he was a cop who was disgraced for some questionable action.
Len was shown to be a brutal, sadistic and cunning individual. He appeared to be a loyal member of the Claimer's, though in contrast to his other group members, did not follow the rules to the same extent. He appeared to be a capable fighter as seen when he took Tony down in order to take a bed away from him. Through words exchanged between him and his group after discovering Michonne's shirt, it is more than likely that Len was a rapist and appeared to be eager at the chance to rape her once she returned to the house she, Carl and Rick were staying in. It is hinted that he has raped and murdered many women as shown during a conversation with Daryl in which he questioned him about Beth and warned him that women like her do not last long in the new world.
Len appeared to despise Daryl for the short time they knew each other after he was forced to share a rabbit with him and cunningly attempted to frame him in order for his group to beat Daryl to death for disobeying the rules, though this plan would backfire as Joe witnessed what really transpired, which led to Len's own death at the hands of his fellow group members.
Len is one of the men who unknowingly invade the house Rick Grimes is resting in. He is first heard downstairs along with his fellow group members apparently either torturing or murdering a man they have been holding captive. After arriving upstairs and getting an argument with fellow gang member Tony over the bed that Rick is hiding under, Len strangles Tony until the latter has passed out. Len doesn't hear the utterings of Tony, who noticed Rick under the bed and was attempting to tell him. A survivor is later heard screaming, most likely due to Lou reanimating.
Len is first seen with his group gathering around Daryl Dixon, while Daryl is sitting down in the middle of a road. After Daryl punches their leader Joe and points his ready-to-fire crossbow at Joe, Len and the other group members point their weapons at Daryl. Len then says that he claims Daryl's vest, because he likes the wing patches on the back of it. After Joe talks Daryl into lowering his crossbow, Len and the other group members lower their weapons too.
At the beginning of the episode, Daryl is seen hunting a rabbit, but just before he is about to shoot the rabbit, Len shoots it dead first. Len then "claims" this rabbit. The two begin to argue, but Joe breaks it up before it comes to blows. He explains to Daryl that according to the rules of their group, if you "claim" something, then it is yours. Joe also tells Daryl that any rule breakers will be punished by beatings or worse. Joe then splits the rabbit between Daryl and Len by cutting it in half with his tomahawk when they still can't reach an agreement. Later in the episode, Len frames Daryl for stealing his half of the rabbit, but Daryl denies that he stole it. Joe empties Daryl's bag and Len's half of the rabbit falls out. Joe asks Daryl if he stole the rabbit, and again Daryl denies it. Joe then asks Len if he framed Daryl and Len denies it. Joe then punches Len. Joe tells Daryl that he saw Len put his half of the rabbit in Daryl's bag. Joe then orders the rest of the men to beat Len. Later, Daryl wakes up and finds blood on the floor where the men beat Len. Outside, below the loading dock of the building where the group had just stayed overnight, Daryl finds Len's bloodied corpse. There is an arrow protruding from Len's head. It is apparent that Len was murdered by his former group members, either by beating him fatally or shooting him in the head with an arrow.
This list shows the victims Len has killed:
After Joe called Len out on his lying to try to get Daryl beat up, he punched him in the face and subtly ordered his men to kill Len. He is brutally beaten up and then killed by the rest of his group, as evident by the arrow through his eye socket. This is due to Len planting his half of the rabbit in Daryl's bag to frame him for stealing it. Afterwards, an arrow is seen through Len's skull.
- "Teach him gents. He's a lying sack of shit and I'm sick of it. Teach him all the way."
- —Joe regarding Len's behavior[src]
Not much about their relationship is known, but Joe had him killed for breaking the rules of their group and lying, suggesting that any past relationships became null when infractions were made. Joe also mentions that he was tired of Len's bullshit, showing that he did not care for him.
Tony and Len have had a rough relationship. Len bothered Tony about the bed he was sleeping in and sought to take it for himself. This caused the two to get into a fight and Len choked Tony into unconsciousness. After his victory, Len remarks "My bed now, jack-off." However, considering this behavior was normal for the Claimers, it was unlikely that they had any kind of grudge afterwards. Tony however probably did not care much for him as he helped to beat him to death.
Harley was a fellow group-member. It is unknown about their relationship other than that, however Harley did not hesitate to beat up and kill him.
Dan was a fellow group-member. It is unknown about their relationship other than that, however Dan did not hesitate to beat up and kill him.
Billy was a fellow group-member. It is unknown about their relationship other than that, however Billy did not hesitate to beat up and kill him.
Len and the rest of his group come across Daryl sitting down in an open road, and they allow him to join them. In "Us", Len and Daryl are seen hunting together, and Len tries to claim a rabbit that Daryl killed, and proceeds to talk about how Daryl must have lost a young woman, and how "the little ones" never last, resulting in Daryl pulling his knife on Len. This tension rises after the two settle with the rest of Len's group. Len plants his half of the rabbit that the two split in half in Daryl's knapsack, and calls out Daryl so he will be punished by Joe. Ultimately, Len is beaten after Daryl is proven right. The next morning, Daryl finds Len's body, which had been beaten to death, and contemplates on whether to cover the body with a bed sheet, showing remorse; however, he ends up leaving the bed sheet on the deck instead.