I talked to L. through the mesh wire of a holding cell in the basement of the New Haven County Courthouse. He wore the grime of months living outside like another skin and stared at Carly Levenson, my clinic partner, and me with jaundiced eyes. When we met in the fall of 2014, he was a thirty-year-old recovering drug addict; Carly and I were second year students in the Yale Law School Criminal Justice Clinic. A week before, when I’d been pondering how to introduce myself to a new client, I’d imagine a young black man, like me, not L., a blue-eyed white guy . (L.’s name has been withheld to protect his privacy.) “The Jungle” is what local police officers call the 301-unit housing complex where they picked up L. They figured that any white person walking through that neighborhood must be trespassing and desperate for narcotics. Two officers stopped and questions L. about his presence in the neighborhood. L. told them that he’d been walking through...