High atop a New York penthouse, Tess is entertaining at a society party hosted by bon vivant Everett Clay when his octogenarian father Benjamin, who still runs the family business, makes a surprise appearance to chastise his son and grandson about their wasteful ways.  The following morning, Benjamin tells Everett the Bible story of the prodigal son who squanders his fortune.  Benjamin reminds Everett that his great grandfather started this company carving handmade buttons and that he’s being disinherited to learn the importance of self-reliance and hard work, handing him a framed deerskin jacket, with buttons carved by his great grandfather.  Angry and penniless, Jake busts the frame, when Tess appears in her Cadillac, offering Everett a ride to Colorado, where some friends of his had invited him to stay.  Before long, they arrive in Central City, the mining town that was in its heyday at the turn of the century.

They stop at the historic Teller House saloon where Everett notices a portrait of a woman’s face painted on the barroom floor.  Tess tells Everett some of the folklore surrounding the fabled portrait, then goes on to tell him its connection to his great grandfather, Jack Clay.  It turns out that the woman whose likeness appeared on the barroom floor worked at the saloon and was friends with Jack Clay.  Tess recounts the story of how Jack had come to Central City to hawk his miracle elixir, preaching its curative powers with the conviction of an evangelist.  Jack loses a game of poker to a known con man named Barkley Stubbs, who not only left town with Jack’s horse and gun, but a bag full of handcrafted buttons he made for his wife.

With Monica and Andrew as his guides, Jack tracks Barkley to a remote mountaintop and finds him unearthing a treasure.  Jack holds Barkley at gunpoint to hand over the treasure.  Monica tries to talk Jack out of it when Barkley makes a move for the gun.  A struggle ensues and the gun goes off, wounding Barkley.  Physically unable to reach the nearest hospital, Barkley prepares to meet his Maker.  But before he does, he advises Jack to put his button-making skills to use, and gives Jack the map to find his way back to Central City.  Tess explains that Jack left the treasure intact, taking only his due.  Realizing what this means, Everett searches the deerskin jacket, finds the treasure map and returns to the spot to unearth the treasure his great grandfather buried over a hundred years ago.  But when he opens it, he is flabbergasted to find a lone button — the button that came off during the struggle between his great grandfather and Barkley Stubbs.

When Everett realizes he’d come all this way for naught, Everett goes into cardiac arrest.  He’s rushed to the hospital and while the doctors work on reviving his body, Monica goes to work on his soul.  With Monica’s help, Everett finally comes to understand the lesson his father had been trying to impart.  When Everett regains consciousness, he calls his father to apologize and to assure him that he’s coming home a changed man.