Timothy Olyphant's Raylan? Walton Goggins' Boyd? Jeremy Davies' Dickie? ID all the main players, and see where they're at as season 3 begins
Wynn Duffy is a businessman who handles security systems for Lexington's wealthy, has ties to Dixie Mafia member Emmitt Arnett (Steven Flynn), and first tangled with Gary, Winona's ex, when they were still married in season 1. Gary had borrowed money from Arnett for a real estate deal that went nowhere. Duffy was sent to collect and threatened Winona. Winona asked Raylan to step in. Gary handed over the deed to the land to Arnett, explaining to him that even then it was worth about what Gary owed him, and in the future it would be worth far more. Arnett was fine with this, but Duffy, who was supposed to get paid out of the cash Gary handed over, wasn't.
In season 2, Gary made more poor financial decisions while going through his divorce with Winona and put out a hit on Winona with Duffy so they could collect the insurance money when she died. After one failed attempt, Raylan figured out the plan and could have used Gary to put Duffy away but he knew that if Winona learned that Gary, who'd tried to call off the hit, had wanted her dead, it would have torn her apart. So Raylan took Gary to see Duffy, who'd been going to kill Gary to tie up loose ends, and assured him that Gary was leaving town (he hasn't been seen since). Raylan also told Duffy, whom he was essentially letting walk, ''The next time that we have this conversation, there won't be a conversation.''
Image Credit: FX