In Windfall, Playwright Tarell Alvin McCraney Asks If Money Is a Substitute for Justice

Only a short list of playwrights makes the cut when Chicago’s Steppenwolf Theatre decides to produce a world premiere. Samuel D. Hunter and Branden Jacobs-Jenkins are among them and the company’s faith in these artists has proved well-placed. Hunter’s Little Bear Ridge Road and Purpose by Jacobs-Jenkins both transferred to Broadway after premiering at Steppenwolf in 2024; the latter won two Tony Awards, including Best Play, and the Pulitzer Prize for Drama. Tarell Alvin McCraney is another writer in that select group. While planning Steppenwolf’s 2025–26 50th anniversary season, artistic directors Glenn Davis and Audrey Francis were eager to include a world premiere by McCraney, who joined the Steppenwolf ensemble in 2010. The in-demand playwright agreed, and the resulting drama, Windfall, opens April 9 under the direction of Awoye Timpo (it runs until May 31).

“Tarell is one of the great artists of his generation, a brilliant writer,” says Davis, a close friend and collaborator of McCraney’s who has acted in several of his previous plays at Steppenwolf. “I think for him to come and write this play for Chicago is a huge testament to how he feels about this city.”

At age 45, McCraney has an impressive resume: he’s a MacArthur Fellow, author of The Brother/Sister Plays trilogy, and the Academy Award-winning co-writer of the 2016 film Moonlight, which is based on his own semi-autobiographical play. He’s also an accomplished educator and administrator, currently a faculty member at Yale University (where he recently co-chaired the playwriting program) and the artistic director of the Geffen Playhouse in Los Angeles.

While many of his previous works are set in McCraney’s hometown of Miami or elsewhere in the southern United States, Windfall takes place in Chicago, where a Black father named Mr. Mano (Michael Potts) loses his youngest child to a police shooting. In response, the city offers him a large cash settlement, an amount that would propel him up the economic ladder yet provide cold comfort for such devastating grief. With the voices of his older child, Marcus (played by Davis), and three visiting strangers urging Mano to take the money, the play raises difficult questions about capitalism, justice, and the worth of Black bodies.

“I really feel strongly that we have a kind of affinity or religiosity or a belief system around money that we don’t really interrogate,” McCraney tells Playbill. “Can money mete out justice? Can it defer harm? Can it protect us? Most people believe it can, and that is kind of astonishing.”

Chicago has a long history, not only of police misconduct, but also of paying settlements to victims or their families. According to The Chicago Reporter, police-related verdicts and settlements cost the city’s taxpayers more than $1.11 billion from 2008 to 2024. This context was top of mind for McCraney as he wrote Windfall.

“I often call Chicago America’s first city, because all of the issues that we wrestle with day-to-day are more transparent here than they are in other places,” suggests McCraney. “You sort of have to dig for them in other cities. Where I’m from, Miami, we sort of pretend like these things don’t happen all the time. I don’t want people thinking I’m coming down hard on Chicago, because I love that about Chicago. I love the fact that, with the flaws, there is at least a hope to be transparent.”

McCraney often draws on mythological and literary sources in his writing; The Brother/Sister Plays incorporate Yoruba mythology, and his 2013 play, Head of Passes, was inspired by the biblical book of Job. In that same vein, Windfall is intended to have a fable-like quality, and its text contains numerous biblical allusions. Structurally, the play explicitly evokes Charles Dickens’ A Christmas Carol, with Mano’s three visitors mirroring Ebenezer Scrooge’s ghostly guests.

“Tarell employs so many techniques that he’s learned over the years from other writers, other artists, and then he chooses when he wants to deviate and break the form,” observes Davis. “You feel like you’re doing something that’s very much in the tradition of many writers who’ve come before him, like the Greeks or Shakespeare or Marlowe, and then people like Lorraine Hansberry, Arthur Miller, or Tennessee Williams, all the way up to people like Lynn Nottage. But at the same time, he chooses where he wants to make his own mark.”

Timpo, a Brooklyn-based director who made her Steppenwolf debut directing Ngozi Anyanwu’s Leroy & Lucy in 2024, is also a longtime admirer of McCraney’s work. The two first met nearly 20 years ago when she was the assistant director an early production of The Brothers Size, the middle play of The Brother/Sister Plays triptych. With Windfall, Timpo hopes to communicate both the “macro and micro” modes of storytelling apparent in McCraney’s writing. Windfall may be set in Chicago, but Timpco observes, it should resonate anywhere in the country. “I think the thing that’s so brilliant about Tarell’s writing is that it’s always rooted in a very ancient type of storytelling that connects the personal with the cosmic.”