Devon Rodriguez’s portrait of the activist and sculptor John Ahearn is evidence of a profound connection between a mentor and his mentee. Ahearn first encountered Rodriguez’s artwork in an exhibition in 2014, when he was captivated by an oil painting the young man had made of exhausted subway riders. Ahearn invited Rodriguez to visit his studio, and the two developed a friendship.

Ahearn made a double cast of Rodriguez, which was a finalist in The Outwin 2016: American Portraiture Today. Now, Rodriguez is an Outwin finalist himself: “I figured I should add to the conversation and do a painting of John. I wanted to portray him as I saw him: an intense, anxious artist with a hint of anguish. Something that I learned from his work is that every portrait he does transmits something about the subject’s psychology, whether it’s intentional or not.”