Perhaps not surprisingly given the episode title or advanced press releases, the season opens with Raylan on the stand giving reluctant testimony about that time when Dewey was made to think he'd lost his kidneys, which seems like a hundred years ago but has actually been only a few months or so in show time. When Dewey's lawyer dangles the threat of a class-action lawsuit against the Marshal Service and the FBI -- using Raylan's supposed/actual abuse of Dewey to do it -- Vasquez agrees to a $300K payoff. And Dewey's not the only Crowe on the show anymore, as we're introduced to his cousin Dylan, who's not necessarily brighter than our Dewey but is definitely more dangerous, as the first thing we see him do is kill a dirty Coast-Guard-associate of his family's for making fun of his stutter.

Art wants to send Raylan to Florida to investigate Dylan's Cuban career-criminal associate (oh-by-the-way-ing that this would give Raylan a chance to see his daughter), but Raylan instead goes to chat with Dewey, and you know what he did with his ill-gotten gains? Bought Audrey's off Boyd, of course! And hired Wade Messer, who's out of prison, to help! Dewey knows nothing -- it may surprise you to hear -- so Raylan heads off to Miami, which always ends up well for everyone. (To wit, Raylan later video-chats with Winona and his daughter, but skips any mention of the fact that he was in their town.)

Ava's in jail and Boyd tells her he's going to do whatever it takes to influence the legal system sufficiently to get her out, but first he has more Northern fish to fry, as a truck from Detroit meets with Boyd in what's supposed to be a normal drug delivery/purchase -- you'll remember SERIES REGULAR Wynn appointed Boyd his Detroit heroin rep in last season's finale and meant it this time -- but with Detroit "in free fall," as the traitorous yet hapless driver tells Boyd before Boyd kills him, no product is actually delivered. One of the other guys wings Boyd in the ear before he meets his maker, so in frustration Boyd calls Wynn and tells him they're taking a trip to Detroit.

They climb fourteen floors in a dystopian hollowed-out industrial space and demand their drugs from Picker -- who answers by shooting Sammy Tonin in the back of the head and spraying Wynn and Boyd with his blood, which at least isn't a new experience for one of them. This all is part of Picker's plan to pay off some Canadians to whom Sammy was in debt for seven figures. Boyd and Wynn aren't taken so easily, though, and end up capturing Picker, who sets up a meeting with "the Canucks" (one of whom is played by Dave Foley, like, this casting is blowing my mind), who are done with doing business with incompetent US criminals but agree to give Kentucky one more shipment, whereupon Picker offers to broker new business for them in Mexico. It's all trust and good feeling from here on out, I'm sure.

In Florida, the local marshals tell Raylan about Dylan Crowe's partner in the Coast Guard officer's demise -- he's a Cuban national who works for the Crowes as a family enforcer, and the family business is currently selling embargoed Cuban sugar (not a euphemism) at below-market prices. Raylan and Deputy Marshal (I'm assuming) Dave Koechner head out to confront the entire Crowe family, the undisputed leader of which is Michael Rapaport's Darryl Crowe Jr., whom Raylan put in prison during his stint in Florida. Darryl is none too pleased with his brother's incautious murder of the Coast Guard dude and orders him to take the corpse to "the Haitian" for disposal. They have to wait in the swamp's reeds, though, because Raylan gets to the Haitian (played by Edi Gathegi of X-Men: First Class) first, with whom he has a bit of a history as well.

Raylan lets it drop to the Haitian that Dewey has recently become flush, while Darryl sends his sister Wendy (Alicia Witt), a paralegal, to Raylan to try to negotiate an end his parole probation, offering his Cuban associate as a bargaining chip. Raylan agrees, so Darryl pays off the Cuban and his teardrop tattoo to go on his way, surreptitiously setting him up for Raylan to get him and figuring he and Raylan will kill each other in a firefight; he then has another brother "Danny" (A.J. Buckley of CSI: NY) off Dylan for his incompetence. I'm kind of glad, because with Dewey around there's really only room for one criminally stupid Crowe.

The Cuban is also smarter than his associates guessed, as he stashes a gun in Wendy's car and uses it to take her prisoner, but she too shows some resourcefulness as she swerves her ride into a collision on the passenger's side, allowing her to escape the vehicle ahead of the momentarily dazed Cuban. Wendy calls Raylan and tells him what happened, so he and Deputy Marshal Dave Koechner head for the marina from which the Cuban plans to escape back to his homeland, and the two marshals end up shooting the Cuban dead when he draws on them. Raylan reports back to Darryl the next day and tells him their deal is done, and later -- with their sugar business gone -- the Haitian brings up Dewey, so you can bet Darryl's going to be visiting Harlan to see how much of that 300K he can get his hands on.

In the end, Boyd's efforts to get Ava out are not going well, so he goes to Lee Manners to try to bribe him for his influence, but Lee Manners offers him a different deal -- he can lie in a sworn confession that he killed Delroy and forced Ava to move the remains. When Boyd says nothing, Lee Manners sneers that he knew Boyd didn't love his "white-trash fiancée" enough to make that sacrifice -- whereupon Boyd beats Lee Manners with his gun butt, apparently to death. He offers to pay off his (mail-order?) Latvian doctor wife rather than murder her too, and she agrees -- but when he's gone, she rushes to her husband and whispers she'll take care of him. So either he's still alive and she's going to treat him, or she's going to use the resources of his funeral home to really send him out in style.