In Al Capone Shines My Shoes, Al Capone appears as a representation of the nature of celebrity and notoriety. While Capone is famous as the island’s most notorious prisoner, Moose must deal with the complex nature of Capone’s personality and behavior: While the gangster is sometimes charming and kind, there is also a hint of menace just below the surface.

Moose’s direct dealings with Capone leave him with mixed feelings about Capone. On one hand, Capone appears an attractive and alluring person. When Moose asks him to help Natalie get into the specialist school for neurodivergent children, Capone obliges. Moose later meets Capone in person twice in the novel. During the first visit, Capone humbly offers to shine Moose’s and his father’s shoes and behaves in a very complimentary and gracious manner toward Moose. Moose is starstruck by this encounter, even telling his father afterward that he would vote for Capone as president. In the second encounter, Capone is cradling Darby’s missing baby. Capone treats the baby with tenderness, presenting himself as trustworthy and well-meaning.

There is, however, another and much darker side to Capone. Moose witnesses Capone spitting into the food prepared for the guests of honor at the banquet, including the food of the man who put Capone behind bars.