A death row inmate, Wesley Archer, writes to Peggy claiming to have been touched by her substitute teaching. Peggy visits him in prison and brings him books to read, much to the disapproval of Hank. Finding that Wes is illiterate, Peggy begins tutoring him. She plays Boggle with him and gives him the Boggle set to use. At their next meeting, Wes tells Peggy that the Boggle timer was destroyed in a fight, and that his friend will give her a new timer to bring to him.
Meanwhile, Dale, inspired by hearing about Peggy's visiting the prison, wants to become an executioner. The warden accepts Dale's offer to spray the entire prison for $1. Dale then states gleefully that according to the prison manual, he is eligible to become an executioner. The warden agrees to add him to the long waiting list, but erases his name after he leaves the room.
Peggy gets the over-sized timer, packed to the brim, from Wes's friend. Later Wes claims that the sand spilled out of the timer, so Peggy retrieves a brick of "timer sand" from his friend. Soon Wes admits to Peggy that the timer sand was actually cocaine and that he has been using her as a drug mule. He tells her that he had written all of the teachers in the Arlen yearbook and she was the only one naive enough to respond. As Wes tells her, "I never had you as a teacher! I'm from Arkansas. I'm almost 40 for God's sake!"
Wes threatens to turn Peggy in unless she brings him a list of items including a "box of pornography, a jug of corn liquor, a Farrah Fawcett poster and a Milwaukee Sawzall," as well as a brick of cocaine every week. The deadline passes, and Peggy is called to see the warden. Peggy and Hank go to the meeting to find that the only evidence against Peggy is the empty timer, which "looks like it's been licked clean." With no evidence, Peggy is absolved of the crime, and Wes is arrested.
On the way home, Peggy says that "someone" owes her an apology, which means she's talking about Hank. Hank apologizes, but when he doesn't know what he's apologizing for, Peggy accepts and the episode ends.
- When the prison warden erases Dale's name from the list of executioners, one of the other names listed is Alex Delarge, the main character from the Anthony Burgess novel (and Stanley Kubrick film) "A Clockwork Orange".
- Another name on the list of executioners is one of the the writers of the episode John Altschuler.
- The main antagonist of the episode, Wesley Archer, is named after the episode's director, Wes Archer.
- The title is a reference to the popular phrase "death and taxes".
- In the real world, the cocaine in the Boggle timer would have been detected well before it passed through the checkpoint and Peggy would have been detained immediately for questioning.
- Bobby's essay that Peggy covers up with Wesley's drawing reads: "Some people might try to tell you that pollution is good. I think they are wrong. From all the research I have done it seems to me that pollution is bad. Very bad. Pollution makes the sky a funny brown color and that is bad. The only way to stop all this pollution is if we will just stop spilling oil and throwing our garbage around. My dad says that if we all used propane there would be a lot less pollution because propane is a clean burning efficient fuel. I am so sure that pollution is bad that when I get this paper back I will never throw it out."
- Wes is seen again in the Season 11 episode Glen Peggy Glen Ross as Hank is leaving the prison. He is next to the prisoner Hank spoke with regarding the golf clubs.
- Peggy's naivety shines in this episode as she believes Wesley was a former student of hers (even though he's almost 40) and believes the timers are not suspicious. She also believes that he is illiterate, even though he wrote a letter to her earlier. Her naivety becomes a focal point in many future episodes.
- Peggy reveals that Wes was dealing the cocaine to the Aryan Brotherhood.
- When Wesley Archer asks Peggy Hill to translate “Peggy Hill is the smartest, most talented woman on earth” in Spanish, she mistranslates it as “Peggy Hill es bueno.” A more accurate translation would have been “Peggy Hill es la mujer más inteligente y talentosa en el mundo.”
- Bobby: "All sloppy and no joe."
- During the scene in the warden's office where Peggy is accused of smuggling cocaine, the timer is sitting empty on the warden's desk. But after Peggy denies the accusation, the timer is shown full.