In the season 2 episode "Mr. Monk and the Captain's Wife", Karen is badly injured after a sniper lethally shoots a tow truck driver, sending the truck into a head-on collision with Karen's car. Leland is left with the same type of pain that Monk has learned to deal with. His emotions nearly get the better of him twice, first when confronting a labor union boss he believes to be implicated in the shooting, and then when arresting the actual criminal.