"Hatless" has Raylan losing that signature ten gallon cowboy hat when engaging in a drunken brawl outside a bar with a couple of yahoos. He's in a bad way at this moment with the Ava ordeal and soon having to deal with Winona's safety (and her realtor husband's predicament with a loan shark (and the loan shark's "middle man", Duffy)) doesn't help matters. So Raylan will try to get Winona to a safe place, find Gary, and hope to find a way to smooth all this over without bloodshed. Duffy is the current "advocate" for Emmitt Arnett (Steven Flynn), and it is about loaning money for this grand "investment" in Gary's shopping and family center. The money's due and Gary simply doesn't have it because of the current state in real estate. Winona has her share of angst with Raylan, always emphasizing her true love and care for Gary, just wanting him to remain safe (and she doesn't want Raylan to gloat about Gary's troubles). Although it would appear, "Hatless" is a one-off for the Duffy character (he gets "winged" during a shootout after pulling his gun in protest to Arnett's acceptance of the contracted property, sure to accrue in value over time), he would become one of many thorns in the sides of Lexington law enforcement. This is more about the ongoing triangle between Raylan, Winona, and Gary; the likes of Duffy--as a character proving that he plans to collect on what he believes he's owed--are part of the criminal element always at odds with Raylan and the US Marshals. Gary gets an old buddy (a UK football star with a Super Bowl ring) involved, meeting Duffy, using Toby (Malik Yoba) as his intimidating muscle. However, Duffy has "muscle" of his own, a broken-down (but tough little fella) featherweight named Billy Mac (Travis Webster). Billy Mac may not be much to look at but he's a nasty little bruiser who seriously roughs Toby up. Raylan, though, makes a statement by taking Billy Mac's own gun and threatening to use it on him if the guy doesn't clue him in. The "meeting" is rather funny because Duffy, not Arnett, is irate that the money isn't available. Duffy is a man that wants his cut; of course, Raylan gets out of this crazy scenario yet again. Raylan's got a guardian angel. Oh, and you can guess that hat's coming back to its rightful owner, too.