Friendship and loyalty are at Taking Sides’s core. The story develops this theme through Lincoln’s two closest friends, Tony and James. Tony is the “old friend” from San Francisco’s urban Mission District who has known Lincoln for most of his life. James is the “new friend” who lives in Sycamore, the affluent San Francisco suburb where Lincoln and his mother have just moved. Lincoln is conflicted throughout much of the story because he is unsure how to exist in both his old world and his new, and Tony and James are markers for this aspect of Lincoln’s arc. The parallels that exist between Tony and James underscore both that one can have friends in multiple places and that true friendship is not affected by physical or temporal distance.

Tony is almost as important as Franklin or the Mission District itself to Lincoln’s perception of himself and the world around him. The book opens with Lincoln and Tony talking on the phone about Lincoln’s new neighborhood and school, which demonstrates that the friends are still close despite the physical distance between them. However, the physical distance becomes emotional distance as the narrative develops. During their argument about the TV’s theft, it seem as though Lincoln’s changed circumstances now divide them; Tony accuses Lincoln of succumbing to middle-class, “white” naivete, while Lincoln, newly put off by Tony’s attitude, fails to recognize that Tony has Lincoln’s best interests at heart.