Bobby first appears in "Haymaker", though he is not named until "Undertaker". He is a passenger in the hearse while Abelard is driving it in pursuit of Rocky and Ivy, ultimately striking Rocky in "Haymaker". After getting out of the hearse, Bobby refers to Abelard as an "ordained maniac", and points out that the hearse has been significantly damaged during the chase. Bobby seems less concerned with the possibility that Ivy and Rocky may still be in the area than with the damage to the car. Ivy threatens Abelard and his associate with a gun that she took from their hearse in "Jellybeans", though after Bobby indicates that he believes Ivy and Rocky are just trying to steal their liquor, Ivy points out that they intended to purchase it. However, Bobby states that their simply being present is now an issue. In "Brimstone", Abelard advances on Ivy and demands that she give him the gun, but quickly backs down when she fires several bullets into the hearse. Ivy asks them what it will take to convince them that they are all on the same side, and Bobby asks what bootleggers Ivy is affiliated with.
In "Undertaker", Bobby and Abelard take Ivy and Rocky's unconscious body to the Arbogast Funeral Home. Elsa asks about Rocky, and it is quickly made clear that she and Bobby are close. Bobby asks Elsa to tend to Rocky's head wound, and in "Medicament" reveals that he met Elsa overseas shortly after World War I. He goes on to tell Elsa that Ivy claimed she was sent to them by Viktor, and the three of them discuss their past associations with Lackadaisy. While Elsa considers Atlas to have been, "mild, softspoken", Bobby seems dubious, referring to Atlas as, "softspoken and positively Machiavellian", especially when in the company of Viktor and Mordecai. In "Gravediggers", Bobby continues to relate the story of their involvement with Lackadaisy, though he is cut off by Elsa, who asks him not to tell Ivy more "awful stories". However, Ivy is eager to hear more, and Bobby continues his story in "Bushwhack" through "Powder-keg".