When I Was the Greatest explores different ways the concept of family, and one’s relationship to family, can be defined. Reynolds achieves this primarily, but not exclusively, through Ali and Noodles’s interactions with their siblings and mothers. This allows for a more expansive and realistic representation of African American single-parent households.

The similarities between Ali and Noodles’s families ironically double as points of contrast in their family dynamics. For example, both boys live in female-headed single-parent households, but their mothers’ approaches to parenting could not be more disparate. Both mothers are often away from home, but Doris makes sure there is food for Ali and Jazz—enough even for Noodles. Conversely, the James brothers live in a house so bare that that it “didn’t even have frozen water” (134). This basic aspect of care considered a norm in most families, including Ali’s, is entirely absent from Noodles and Needles’s family. At one point, Ali is dumbfounded when their mother Janice “ran down the stoop, passed Needles, and into the black cab. She didn’t even acknowledge him” (65). Actions like these, and her general lack of affection for her children, make Janice a perfect model of the stereotypically neglectful single mother.