What is the “Golden Gift of Grey” in the story and who gives Jesse this gift? What does it mean to Jesse?

The most direct answer to this question is that Everett Caudell gives Jesse a proposal to not do what his parents tell him to do, (return gambling money he got from winning games of pool), in a way that releases Jesse from the guilt he feels about disappointing his parents.

What seems a simple choice on the surface actually has much deeper meaning to Jesse and is experienced as a problem that goes to the very heart of his character and his relationship with his parents. It is a coming-of-age moral dilemma that every one of us is faced with in adolescence: the internalized expectations of his parents vs. his own personal ambitions. 

Jesse’s parents have a very black and white view of morality that has shaped Jesse’s conscience.  The author describes this metaphorically in the opening paragraph of the story when Jesse is watching the clock and feeling guilty for making choices he knows his parents disapprove of:

“There they were, perfectly vertical, like a rigid arrow of accusation seeming to condemn by their very rigidity and righteousness everything in the world that was not so straight and stern as they themselves.” (p.59)

Jesse is a bright student who does very well in school but has parents who lacked education. He feels his parents do not understand him and that he does not understand them well either.  He has grown up with conflicting feelings of respect and shame for his parents and the label of “hillbilly” that the town has for his family.  He begins spending time in small local bar where he learns how to play pool by watching others play and practicing on his own.  Jesse knows his parents would not have allowed him to be there, so he keeps his activities a secret from his family for two years.  Then a day comes when Jesse decides to play games against the men for money and surprises himself by winning again and again.  He decides not to go home even though he knows this will cause a conflict with his parents.  As the night goes on, Jesse has a constant inner conversation where he imagines his parent’s disappointed reaction.  It makes him feel so guilty that he does not feel any joy in his accomplishment.  Before going home to face his parents, Jesse comes to the conclusion that he will give his winnings to his parents and this gives him great relief from the guilt he felt for his wrongdoing.

“It would be the first worthwhile gift that he would give to those from whom he had always taken.  And he was filled with a great love for the strange people that were his parents.  Parents whom he found so difficult to understand… And he was ashamed now of the times he had been ashamed of them.”  (Pp. 73-74)

When he returns home, Jesse’s parents react how he expects by being upset and questioning his whereabouts.  However, when he offers them the money he is surprised that they refuse to take it and insist that he return the money because it was earned by gambling which is against their values.  Jesse obeys his parents by going to the house of Everett Caudell who helped him learn to play pool and was the first person Jesse had won money playing against.  Everett invites Jesse into his house and Jesse ends up confiding very emotionally to the older man about his conflict and then giving Everett the gambling money.  Before Jesse leaves, Everett stops him and the most significant point of the story happens:

“Before he could move he saw the older man quickly and quietly tuck the three bills into the shirt pocket of his guest.” Now there, “he said, “there ain’t nothen wrong.  There’s no lie. You give it to me and I took it.  We’ll leave it be like that.”  (p. 78)

Everett shows Jesse the “grey area” in between the black and white definition of his parent’s code of morality.  At this point it really isn’t about Jesse keeping the money or not, it is about Jesse feeling redemption for his wrongdoing.  As the story ends it is clear a weight has been lifted from his shoulders and it is implied that he will now be focused on school and living according to his parent’s expectations.  The story is a perfect parable for the Catholic idea of confessing to a priest one’s wrongdoings to be released from the burden of sinning against God and then going forth with a clean slate to “sin no more.”  Or in psychology it could be an allegory for the id (the impulses and urges we feel a desire to act upon), the superego (the inner parent, morality, or conscience), and the ego (the mediator that can come to a rational compromise between the id and superego).