How a Playwright Became One of the Most Incisive Social Critics of Our Time

In person, Jackson at first seems unassuming and even shy. He does not reflexively generate small talk. But he responds candidly and at length when asked a question about almost anything, and he is wickedly funny. In Jackson’s diagnosis, the fan in question was haplessly inspired by the racial reckoning then gripping the nation; he felt compelled to “show up” in the name of white allyship and anti-racism. Jackson compromised with his would-be savior: For the benefit of the latter’s conscience, he’d accept the vest’s cash value of $400. The man promptly sent this sum to Jackson via Venmo.