The fifth episode of season 5, “Shot All to Hell”, is by far the best episode of that season. It is so good that I feel comfortable, after a re-watch, in saying that it belongs on the list of the series’ all-time greatest episodes. It’s absolutely terrific.
And yet, season 5 is clearly the weakest of the “fully serialized” seasons (meaning besides season one, which was a different sort of show). So what went wrong?
I think I figured it out: “Shot All to Hell” should have been within the last three episodes of the season.
A ridiculous amount of stuff happens this episode (spoilers for those who care). Theo Tonin is caught, Lee Paxton is killed, Sherriff Mooney is killed, the case against Ava collapses, a guard stabs himself to ensure Ava stays in jail, and Raylan reveals to Art that he was the dirty cop from the Nicky Augustine shooting.
This is a TON of new information for a single episode to go through. Most seasons don’t contain this much change. And this is episode 5 of the season!
The season should have been made up of mostly Ava in jail (while cutting to her as little as possible, because that was a weak plotline), with Boyd’s plan to get her out finally coming to fruition in “Shot All To Hell”, only to have it fail due to the guard stabbing himself. Ava knows nothing about Boyd’s work to get her out, and Raylan by the next episode offers her a way out if she rats on Boyd. She refuses initially but changes her mind when she’s nearly killed in prison.
Meanwhile Art, having just captured Theo Tonin and incredibly pissed at Raylan, is shot by Daryl Crowe, thinking it’s Raylan. And then the last episodes could end roughly as planned. Presumably, and hopefully, the Mexican mafia won’t have worn out their welcome too much, and Raylan would be more involved. You can also have the marshals perhaps start closing in on Boyd, leading him to picking a clean slate over Ava’s release.
The big strength of this season has been that the writers have never lost sight of their end goal. They went into the season with a plan in mind and stuck with it. Season 5 suffered from disorganization, and if it had focused itself in a similar way it had the potential, seen in such classics as “Shot All to Hell”, to be great as well.