Arts & Entertainment
Steppenwolf’s ‘Windfall’ Explores a Father’s Grief and the Value of a Life
A son lost in a clash with the police. A huge cash settlement on the table. And a father torn between staying put in Chicago or starting anew.
That all-too-real dilemma is what underpins the play “Windfall,” a new work by Oscar-winning Steppenwolf Theatre ensemble member Tarell Alvin McCraney that began previews last week. It’s the first play written specifically for Steppenwolf’s Ensemble Theater, with the audience seated in the round — an immersive experience that befits the play’s emotional weight.
“I often talk about the spiritual aspects of theater — that we come into a room and we believe together, and therefore an act of faith is happening,” McCraney said. “In this play, we’re interrogating what we believe. And we believe as a society more than anything that money cures more things than we’d like to admit.”
“Windfall” was commissioned as part of Steppenwolf’s 50th anniversary season. Cast member Glenn Davis is Steppenwolf’s co-artistic director, along with Audrey Francis.
“Usually, actors don’t run theater companies,” Davis said. “I think here at Steppenwolf, because it’s an ensemble theater made up mostly of actors — we also have directors and writers — but we started as an acting company and that very much still is our identity today.”
The cast of Steppenwolf Theatre Company’s world premiere of “Windfall.” (Michael Brosilow)
Among Davis’ castmates are Alana Arenas and Jon Michael Hill, all three of whom appeared in 2024’s “Purpose,” which opened at Steppenwolf and eventually moved to Broadway, winning the 2025 Tony for best play.
“The secret weapon of Steppenwolf, I often say, is the fact that you have these relationships that have traversed time and space over so many years,” Davis said.
That includes Davis’ relationship with fellow ensemble member and “Windfall” playwright McCraney: “not only my best friend, but also” one of the great dramatists of his generation.
McCraney described “Windfall” as the play he was most anxious about writing.
“Money is the key factor in most breakups, in most relationships ending, in friendships going awry,” McCraney said. “Money is the thing that some people say the root of all evil is based on, that wars are started about, and here I was wanting to make a play … about the ways in which monies are attributed to Black bodies, particularly those who are harmed by the city.”
The challenging material appealed to longtime New York-based actor Michael Potts, who’s making his Steppenwolf debut.
“I’d wanted to work here for a very, very long time. I was wondering why I hadn’t been asked!” Potts said with a laugh.
(left to right) Michael Potts, Esco Jouléy and ensemble member Glenn Davis in Steppenwolf Theatre Company’s world premiere of “Windfall.” (Michael Brosilow)
Potts described the material as emblematic of McCraney’s impressive voice.
“You’re going to see an extraordinary wash of emotions and language and concepts coming at you, left, right, center, above and below,” Potts said. “It’s going to be a lot of the unexpected, but it is ultimately going to be a human story that I think everyone is going to relate to. I love puzzles and I love this kind of puzzle he’s created about this character, about these characters, and this story and how it fits in the human experience.”
Despite the heavy themes “Windfall” explores, Arenas said “the play is infused with the joy of community, the joy of tackling something together. … Tarell is very masterful in knowing that we need to have a serious conversation, but choosing a tone that makes it palatable for us to all engage.”
Arenas has known McCraney since high school and an arts community center in Miami. They both went on to study at DePaul University, where they met Davis.
“Maybe more than once our directors looked at us and had to say, ‘Do I have to separate you?’” Arenas said with a smile. “There’s a lot of playfulness in the room but it’s cozy, you know? Like an old comforting sweater.”
Steppenwolf has previously staged several of McCraney’s works. He’s also well known as the writer of the Oscar-winning film “Moonlight,” adapted from one of his own plays. Recently, “Sinners” writer-director Ryan Coogler joined McCraney as just a handful of Black artists with a screenplay Academy Award.
Playwright/ensemble member Tarell Alvin McCraney in rehearsal for Steppenwolf Theatre Company’s world premiere of “Windfall.” (Jeremy Williams)
Asked what it was like to see Coogler on the Oscars stage, McCraney said: “Oh, man — I might cry. It was extraordinary … and the way in which he holds his community so close and that he’s a leader in the community, it was astonishing to see.”
As Steppenwolf marks its 50th season, the artists working on “Windfall” are cognizant of the history they’re carrying on and helping write.
“The initial group of ensemble members who started in the mid-70s, they’ve played husband and wife, brother and sister, brother and brother, father-son, mother-daughter, all the things over what essentially is 50 years now,” Davis said. “To be able to know someone that well is a gift.”
Directed by Awoye Timpo, “Windfall” also features ensemble member Namir Smallwood, who recently appeared in “Bug” on Broadway with Carrie Coon. “Windfall” has its grand opening Sunday and begins its regular run Tuesday. The play is scheduled to run through May 31.
Contact Nick Blumberg: [email protected] | (773) 509-5434 | @ndblumberg
WTTW News arts coverage is supported by the JCS Arts, Health & Education Fund of the DuPage Foundation.
