The Prologue opens with the sudden and magical appearance of The Confidence Man who immediately begins to work his wiles and confidence games. With each new game he changes his costume; and with each change, another man appears-dressed in the clothes he has just discarded. In this fashion three men appear, Avatars of the Confidence Man, to form a metaphor for his multi-faceted nature. To make the point that man lives or dies by trust and faith in his fellow man, he invites the audience to come with him to Crystal City on the Mississippi where the story of China Aster will unfold and prove his thesis.

The townspeople go about their business while a young peddler hawks his wares. The Confidence Man and his Avatars stroll about arousing great interest. The Missourian engages The Confidence Man in an acrimonious dialogue and the “great hoaxer” illustrates his point by acting out a story with one of his Avatars. In the next scene China Aster, a candlemaker, appears with his wife, Annabella. They are a struggling, loving young couple. Orchis, China’s friend, who has won a lottery prize, offers China a check for one thousand dollars to improve his business. Annabella refuses to take Orchis seriously and leaves. Orchis then entices China into taking the check and giving him a 4-year note. When China thinks better of it and tries to retrieve his note, Orchis departs, leaving China distressed and in conflict. China attempts to return the check once more, but Orchis, together with The Confidence Man, encourage him to cash it. China is further enticed by a dream of The Angel of Bright Future who showers him with gold and makes him believe that cashing the check will completely change his life. Later, when he tells Annabella, Old Plain Talk and Old Prudence of his vision and his determination to follow his dream, they ridicule Orchis and dreams of riches. A heated argument ensues which sends the old men off in a huff. Annabella tries to warn China against his dream, but to no avail.

One year later, at the Barber Shop, Old Prudence is trying out his counterfeit bill detector to the amusement and annoyance of the Barber. The Confidence Man enters, followed closely by Old Plain Talk, from whom we learn that China has fallen on exceedingly hard times as a result of the loan, and that Orchis, dramatically changed, has returned to get his money back. Not only is he married, but he has joined a religious sect. The two old men rush out to find China and tell him the bad news, leaving the wily Barber and The Confidence Man to play out still another version of the con-game.

When Orchis and his wife appear at the Candle Shop, they find China and Annabella also drastically changed. Orchis is determined to get his money and leaves, demanding that it be ready for him in three days. China, already despairing, loses all hope after another visitation from The Angel of Bright Future, who, this time, shows her harsh and cruel nature. She blames China for his troubles, criticizing him for losing his faith and confidence. Meanwhile, the long-awaited Minstrel Show has come to town. In the climax of the minstrel production, China rushes onstage, pursued by angry creditors. The real and unreal dramas collide; China falls to the ground. Annabella accuses the townspeople of bringing about China’s death, lashing out at them for their vileness, yet asking for their help and sympathy. Old Plain Talk and Old Prudence each take her by the hand when The Confidence Man directs the men to take down the door of the Candle Shop so that China can be carried home.

In the Epilogue, Old Prudence reads China’s epitaph. China has attributed his troubles to putting his faith in a “bright view” of life rather than heeding “the sober view,” but Old Prudence believes otherwise. According to him, the “root of it all was a friendly loan.” The people disperse; last to go are The Confidence Man and his Avatars. Their final words are, “Something yet may come of this masquerade.” The lights go down. When they come up again, the entire cast is assembled onstage, giving voice to the sentiment that no matter what happens, life can go on only if we place the trust of perfect confidence in each other.