In "What You Pawn I Will Redeem," Jackson is challenged by his own character traits and flaws when trying to earn the $999 that it will cost to buy his grandmother's regalia from the pawnbroker. For example, at one point along his journey, Jackson wins $100 from a lottery ticket, but instead of pocketing all his winnings, he gives $20 to Mary, the clerk who sold him the ticket, because he says that it's an Indian custom to share the proceeds of winnings. Jackson's good heart sets him back in terms of the money, and his flaws also contribute to setting him back: after he wins the lottery money, he goes to a bar and ends up buying rounds of drinks for himself and others. In addition, on other occasions during the journey, Jackson falls into the grips of his alcoholism and ends up losing money. These are some of the challenges that Jackson faces as he tries to earn the $999.