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This is a "Wild Mass Guess" entry, where we pull out all the sanity stops on theorizing. The regular entry on this topic is elsewhere. Please see this programme note.
Justified
Raylen is the reincarnation Seth Bullock
Due to the actor that plays them.

Raylens hat is the source of his power

Quarles gun will jam
They keep mentioning the possibility of the quick-draw-under-sleeve device pistol jam and screw quarles in the process, if it happens will be in the worst possible time and WILL get Quarles killed.

Rage bubbling just under the surface? Check. Depravity? Check. Mentally unhinged? Check. Maybe Quarles takes Oxycontin to prevent himself from frenzying. When the old woman in "Measures" said he resembled a husky, she must have seen him in lupus form after he killed the drug dealers.

Quarles is a Lannister
Blonde hair? Check. Ruthlessness? Check. Strange sexual appetites? More than check.

Billy St. Cyr is getting addicts off drugs with ibogaine. The unknown drug that Ellen May snorted in "Hole In The Wall" was powdered ibogaine.
Billy's using more than spiritual upheavals to get addicts in his congregation off drugs. He's giving them ibogaine, a hallucinogenic drug that can allegedly ease or eliminate drug addiction. In "Hole In The Wall", Arnold got ibogaine from Billy, transporting it in the play money that Billy uses to advertize his church. Arnold then gave Ellen May ibogaine in a well-meaning attempt to cure her drug addiction. Unfortunately, ibogaine being a hallucinogen, Ellen May hallucinated that he was a monster when he came out wearing a bear costume, so she shot him.

Billy will eventually become a Badass Preacher.
Seriously, why not? Harlan County is definitely a Crapsack World. Even the purest people tend to get involved in crime or take levels in badass. Despite his sister, who seems to be a Lady Macbeth, Billy doesn't seem to want to be a cult leader. He seems to want to be a regular, generic Christian preacher. But, when his sister's operation goes south, and Boyd shoots down the whole congregation, he will begin a Roaring Rampage of Revenge.

Quarles is secretly alive, and will appear midway through Season 4, only to get killed off about two episodes later.
He seemed like he was still alive when his arm was chopped off. Yes, it's likely that he could have bled out. I admit that. But, if he got medical attention quickly enough, he could have lived.

Duffy will eventually become head of the Dixie Mafia
Emmitt Arnett & Robert Quarles are dead and Sammy is ineffectual. Raylan will either kill or put away Theo Tonin by the end of the fourth season, and Duffy will take advantage and manipulate/machete his way into power.
  • Duffy is already the head of the Dixie Mafia which is subordinate to the Detroit mob that Theo Tonin runs. He has no contacts in Detroit and could never take over that operation. If the leadership of the Detroit mob is taken out, Duffy might instead try to make the Dixie Mafia an independent organization (ie not have to pay Detroit their cut of his profits).

Jackie Nevada is a mathematician.
That is the science most useful to a professional poker player.

Shelby is Drew Thompson.
  • Confirmed.

Theo Tonin will take a while to be in the lime light.
Sammy will probably be the Big Bad of season 5. Theo won't be an active threat until season 6. He'll probably reign as the primary Big Bad until season 7, or so. Thus far, Theo has been remaining in the shadows, while his various Dragons have been doing all of his "dirty work". Once Sammy is out, the only other major players are Boyd and Duffy.
  • If the series runs its natural course and does not get abruptly cancelled, you can bet Raylan vs. Boyd will be the final conflict, though.
    • Jossed. Theo's health problems result in his arrest in Season 5.

Loretta and Kendal will become a criminal duo.
They're about the same age, they're both familiar with the crime world, and they're both in state custody. Loretta and Kendal will meet through their mutual social worker (Allison), become friends, and work together as partners in crime.

Gio Reyes will return in Season 6

With Theo Tonin out of the picture, Gio's the only plot thread (besides Wynn Duffy and Boyd themselves) to still be hanging out there. His storyline was never really resolved, and all it would take is Raylan's old boss getting transferred or suffering an "unfortunate accident" to take his vendetta against Raylan off hold. Throw in the fact that he's the one who had Boyd's father killed, and his longstanding connections to Harlan, as well as the fact that his empire remains intact, and he has the potential to be very good penultimate villain (Boyd and/or Duffy will of course be the last one).

The Kentucky Women's State Prison will see a huge crackdown on corruption

Corruption is rampant among the guards, who bring in drugs, collaborate with criminals, and commit sexual misconduct with the prisoners. Someone in a position of authority will notice all this, and heads will roll when it is discovered just how corrupt the prison is.
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