Raylan is a Straight Up Asshole Now
Maybe this is a problem for some people who are tired of TV law enforcement officers being shed in a negative light for constant legal and moral breaches. But the series’ first scene, which inspired its name, immediately let fans know that Raylan isn’t a man afraid to sidestep his badge’s implications to get something done. Part of Raylan’s current problems stem from the hit he put on Nicky Augustine back in Season 4, but he goes even further down the rabbithole of questionable behavior in a variety of ways.

To start off with, Raylan is undeniably a terrible father, as he takes a trip into Florida in the very first episode but avoids visiting Winona (Natalie Zea) and their daughter; he also gets uncomfortable any time the subject of his family is brought up. Second, he is given temporary ownership of a large mansion owned by a Detroit mob accountant, and totally moves into it for a while the accountant is behind bars, uses the house for sexual missions with Alison. And when it comes to official business, Raylan is perfectly fine with letting Wendy shoot and kill Daryl – as a bit of revenge for Daryl shooting Chief Deputy Art (Nick Searcy) – and his best tactic to draw a confession out of Kendal is scaring him into thinking he’ll be spending the next 40 years in a federal penitentiary; he does this with a quasi-psychiatrist session where he talks about killing a pig for the first time and becoming a Marshall just to piss his father Arlo off. To me, this was as much a confession to the show’s fans that he was never cut from virtuous cloth, so why should we expect him to be?

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