After a rash of shootings in his first few months on the job at the Lexington US Marshal’s office, Raylan has been told to take a vacation while being investigated by internal affairs. He attempts to use the time to get reacquainted with his ex-wife, Winona, but instead gets drunk in a bar, picks a fight and gets his butt whupped.
Winona eventually shows up at the bar, but not until after Raylan has been beat up…and had his hat taken. She drives him home and tends to his wounds while the ex-couple discuss her recent security issues, specifically the visit from Wynn Duffy. Raylan confesses to Winona that he visited her husband, Gary, after she gave him a list of names to run and suspects that he’s got himself into something he shouldn’t.
While Winona is dealing with a drunken and beaten Raylan, Gary is off visiting an old friend – ex NFL player and former University of Kentucky star Toby Griffin. He presents Toby with an investment opportunity, but Toby sees right through Gary’s lies. Gary explains that he borrowed some money from a private investor, but his investment has gone south and he needs to pay up, close to seven figures.
Toby can’t loan him the money to pay off his creditor, but he’s willing to be some muscle when Gary goes to talk to Duffy. The pair go down to Wynn’s office and Gary tries to plead his case to Duffy that if the creditor, Mr. Arnett, simple holds on to the investment his money will double in two years. Duffy is more interested in Toby, who looks familiar. Toby tries to threaten Duffy, but he returns the favor, offering Toby a chance to get out before he’s in too deep.
Later that evening, Wynn Duffy and his associate, Billy Mac, pay a visit to Toby and then Gary for a little physical intimidation. For Toby, Wynn simply doesn’t like someone trying to intimidate him. For Gary, he has a message – get him the money by 9am the next morning.
Raylan turns the tables on Duffy and Billy Mac by following the later back to his apartment. After easily disarming him, Raylan strong arms Duffy’s muscle into revealing Duffy’s plan for the evening – abduct Winona to put added pressure on Gary. Out ahead of Duffy’s plan, Raylan picks up Winona and convinces her to let him take her to a safe place. In exchange, he’s going to try to find Gary who Winona hasn’t heard from all night.
After apologizing for Toby for getting him involved in his mess, Gary heads to the site of his failed investment – land for a shopping destination. Raylan finds him there and Gary is suicidal, hoping Winona could collect the life insurance money after his death. The US Marshal is able to convince Gary not to take his own life (mostly because his life insurance policy is void if he does) and promises to go with Gary to Duffy’s office the next morning.
Gary and Raylan arrive at Duffy’s office at 9am as instructed, but Gary does not have the money. Instead he offers to forfeit his ownership of the land to Mr. Arnett, who is present, to repay his debt. Arnett shocks Duffy by accepting Gary’s offer and this does not sit with Wynn or Billy Mac, who are expecting to get paid for their debt collection services. Duffy points his gun around wildly and a shoot out ensues with Duffy, Billy Mac and Arnett’s body guard all getting shot. Fortunately for Raylan and Gary, they’re unharmed and able to walk away.