Dropping into the Spanish-American War, Bogg and Jeffrey find out that the Rough Riders never turned the tide because Theodore Roosevelt was killed by Billy the Kid. The two make another time jump and join up with Billy's gang in an effort to find Roosevelt. However, Jeffrey's over-idealized view of Billy causes friction between him and Bogg, something of which Billy is too eager to take advantage.
This episode includes examples of the following tropes:
- A Real Man Is a Killer: Bogg's perspective seems to be an inversion of this; he's blunt that he doesn't think much of Billy's hair-trigger temper and tendency to solve his problems with firearms. As he says to Roosevelt while trying to talk him out of a gun battle, Billy is the better shot with a gun, but he's no kind of a man at all.
- Broken Pedestal: Jeff encounters Billy the Kid, who he thinks is not honestly such a bad person. He changes his mind after seeing how mean and dishonorable he could be. After seeing Billy preparing to kill Roosevelt, he chews him out, telling him that he used to admire him, to the point of dressing up as him for Halloween, but this isn't what he expected or wanted. Billy just insults Jeff and continues on his way.
- Counting Bullets: Bogg lures Billy into firing the remaining bullets at him. He counts six and then comes out to confront Billy, hoping he counted correctly. He did.
- Cry into Chest: Jeff begins to cry as he hugs Bogg after the fight with Billy.
- Does Not Like Guns: A major conflict between Bogg and Jeffrey relates to this. Billy offers to teach Jeffrey how to shoot, but Bogg refuses to allow it. Even when he needs to take down Billy near the end, he doesn't initiate a gun battle; he just tricks Billy into firing at him till he runs out of bullets.
- Historical Domain Character: Billy the Kid, Theodore Roosevelt and Benjamin Franklin appear in this episode.
- Like a Son to Me: While talking with Bogg, Rita (a woman he rescued in the opening) asks if Jeffrey is his son. Bogg says he isn't, but he wishes he could say that he was.
- The Teetotaler: While Billy's gang are keeping an eye on him and keeping him from going after Billy and Jeffrey, Bogg asks if they have any whiskey to pass the time. When they tell him where it is, Bogg says he doesn't drink and stuns them by throwing the whiskey into the campfire.
- Uncovering Relationship Status: Rita asks Bogg if he's married.
- "Shut Up!" Gunshot: Theodore Roosevelt is trying to organize a posse to go after Billy and can't get everyone to stop what they're doing. He takes a gun and fires a single shot in the air to get their attention.
- Toxic Friend Influence: Bogg's situation throughout the episode should seem pretty familiar to someone who's worried about their child's physical or moral well-being after the child falls in with the wrong crowd.
- Villainous Breakdown: Billy loses it after Bogg lures him into firing all his bullets, leaving his gun useless, and defeats him. He runs around, yelling at the townsfolk to give him a gun and screaming his name to convince them, causing Jeffrey to note that he's not much without a weapon.
- You're Not My Father: A third person variation; Billy mistakes Bogg for being Jeff's father. Jeff, irritated with Bogg at the moment, is quick to correct the misconception.
