The famous writer and civil rights activist James Baldwin was twenty-one when Delaney created this iconic portrait. Baldwin often featured queer male characters in his works, but as an out gay man involved in the civil rights movement, he was often excluded from inner circle discussions of Black liberation. Closely cropped and vibrantly painted, his image jumps out from the canvas, presenting an up-close encounter with the sitter. As in Delaney’s self-portraits, the artist painted one eye slightly different from the other, a pictorial device also found often in Pablo Picasso’s paintings. Of the many portraits Delaney made of Baldwin, this one is among his most direct and expressive.