Think back to the beginning of the season. Remember when Raylan took up a side job bounty huntingto bring in some extra cash? It was a questionable decision at the time considering he is prohibited by the Marshal’s office from engaging in side jobs. Now that Jody, the man he captured, has escaped and killed the two people transporting him to Florida, it looks like Raylan made a very bad decision by getting involved.
Even so, Raylan would likely prefer to deal with the murderous Jody than have to go see Arlo in prison. Art orders Raylan to go because they need more information on Drew Thompson and Arlo is the only one who can help. The scenes between Arlo and Raylan are usually great. They have a caustic, yet easy banter, and there is always the tension of whether or not they can actually love each other considering what they’ve gone through. The answer on that last question is definitely ‘no.’ Arlo is black-hearted, and Raylan has accepted it – which makes their jabs at one another even more fun.