In The Loop Magazine Full Casting Announced for Steppenwolf Theatre's Windfall

Full Casting Announced for Steppenwolf Theatre’s Windfall

Mar 09, 2026 admin_bitlc Features, Music News, Musical Theatre, Reviews, This Just In 0

Steppenwolf Theatre Company’s world premiere of “Windfall” features (top, left to right) ensemble members Alana Arenas, Glenn Davis, Jon Michael Hill (bottom, left to right) and Namir Smallwood with Esco Jouléy (Eli) and Michael Potts.

CHICAGO (March 9, 2026) – Steppenwolf Theatre Company, the nation’s premier ensemble theater company, is pleased to announce full casting for its world premiere of Windfall, a gripping new work by Academy Award-winning ensemble member Tarell Alvin McCraney, directed by Awoye Timpo.

Windfall reunites ensemble members Alana Arenas, Glenn Davis and Jon Michael Hill, who starred in Steppenwolf’s Tony and Pulitzer Prize-winning drama Purpose, joined by ensemble member Namir Smallwood, direct from his Broadway turn in Bug. Rounding out the cast, Steppenwolf welcomes Esco Jouléy (Dying for Sex) and Michael Potts (The Wire, The Piano Lesson–Broadway), both in their Steppenwolf debuts.

Continuing Steppenwolf’s 50^th Anniversary Season, Windfall will play April 9 – May 31, 2026 in Steppenwolf’s Ensemble Theater, 1646 N. Halsted St. in Chicago. Single tickets are now on sale at steppenwolf.org or the Box Office at (312) 335-1650. The press opening is Sunday, April 19, 2026 at 6 pm.

About the Production:

This is a story about money. Don’t let them fool you otherwise. When a father loses his child in a clash with the police, he is visited by three strangers who advise him to take the city’s cash settlement, relocate and forget his grief – or else remain, haunted by memories of the world his child fought so hard to protect. This lyrical world premiere is a vital and timely look at the spirit of activism set against the most indifferent system of them all: the almighty dollar.

Steppenwolf Artistic Directors Glenn Davis and Audrey Francis comment, “When we commissioned ensemble member Tarell Alvin McCraney to write a new play specifically built for our in-the-round Ensemble Theater as a centerpiece of Steppenwolf’s 50th season, we weren’t sure what he’d create. But, given that Tarell is one of the most talented writers of his generation, we were not at all surprised that he delivered a stunning, lyrical and undeniably bold script. This is a play for our moment, for our city, tailor-made for an ensemble cast and this unique venue. We eagerly anticipate sharing this vital Chicago story with our community.”

The creative team includes Andrew Boyce (Scenic Design), Qween Jean (Costume Design), Jason Lynch (Lighting Design), Willow James (Sound Design), Marie Ramirez Downing (Dialect and Voice Coach), Bryar Barborka (Dramaturg), Patrick Zakem (Creative Producer), Tom Pearl (Producing Director), JC Clementz, CSA (Casting), Michelle Medvin (Production Stage Manager) and Kathleen Barrett (Assistant Stage Manager).

Production Details:

Title: Windfall
Playwright: ensemble member Tarell Alvin McCraney
Director: Awoye Timpo
Cast: ensemble members Alana Arenas (First Lady, Second Wife, Miss Second, The Last One) Glenn Davis (Marcus), Jon Michael Hill (Nurse, Cori) and Namir Smallwood (Officer, Brother 1) with Esco Jouléy (Eli) and Michael Potts (Henri ‘Mr. Mano’ Tamaño).

Location: Steppenwolf’s Ensemble Theater, 1646 N. Halsted St., Chicago

Dates: Previews: Thursday, April 9 – Saturday, April 18, 2026
Press performance/Opening: Sunday, April 19, 2026 at 6 pm
Regular run: Tuesday, April 21 – Sunday, May 31, 2026

Curtain Times: Tuesdays, Wednesdays, Thursdays and Fridays at 7:30 pm; Saturdays at 3 pm & 7:30 pm; and Sundays at 3 pm. Please note: there will not be 7:30 pm performances on Tuesday, April 14, Wednesday, April 22, Tuesday, April 28, Tuesday, May 5, Saturday, May 9 (Steppenwolf Gala) and Tuesday, May 26; there will not be at 3 pm performance on Saturday, May 9 (Steppenwolf Gala);; there will be an added 2 pm matinee on Wednesday, May 20.

Tickets: Single tickets for Windfall ($20 – $148.50*) are now on sale at steppenwolf.org and the Box Office at (312) 335-1650. Steppenwolf Flex Memberships are currently on sale at steppenwolf.org/memberships: Black Card Memberships with six tickets for use any time for any production and RED Card Memberships for theatergoers under 30. *Pricing includes an $8.50 handling fee

Steppenwolf offers 20 tickets for $20 (no added fees) for each performance of every membership series production. Use promo code 20FOR20 to redeem this offer online, available in advance until they’re sold out for every main series show. Limit 2 tickets per person. You can also purchase by phone at (312) 335-1650 on the day-of show at 12 pm for main series performances. Limit 2 tickets per person.

Accessible Performance Dates:

Audio-Described and Touch Tour: Sunday, May 24 at 3 pm (1:30 pm Touch Tour)
Open-Captioned: Saturday, May 16 at 3 pm & Thursday, May 21 at 7:30 pm
ASL-Interpreted: Friday, May 29 at 7:30 pm

Education and Engagement:

Throughout the 2025/26 season, Steppenwolf continues its commitment to the next generation of theatre learners, makers and appreciators with robust education and engagement programming. Programming includes dedicated student matinee performances during four of the five Membership Series productions including Mr. Wolf, Amadeus, The Dance of Death and Windfall, in-school residencies in partnership with Chicago Public schools, workshops, panels and events specifically geared towards teens, as well as professional development trainings and resources for educators. Additionally, Steppenwolf is reimagining their community engagement and will pilot new public programming, continue accessibility programming and offer opportunities for deeper explorations for audiences throughout the season. For additional information about Steppenwolf’s Education and Engagement programming and to register your school for a field trip visit steppenwolf.org/education-and-engagement/steppenwolf-field-trip-series.

Artist Biographies:

Tarell Alvin McCraney (Playwright, he/him) is Artistic Director of Geffen Playhouse. In this role, he is responsible for identifying, developing and programming new works and re-envisioned classics. He sets the strategic artistic course for the Geffen’s Gil Cates and Audrey Skirball Kenis Theaters. McCraney is an award-winning writer, producer and educator, best known for his acclaimed trilogy, The Brother/Sister Plays. His script In Moonlight Black Boys Look Blue is the basis for the Oscar–winning film Moonlight directed by Barry Jenkins, for which McCraney and Jenkins also won a Best Adapted Screenplay Oscar. He is an ensemble member at Steppenwolf Theatre and a member of Teo Castellanos D-Projects in Miami, a graduate of New World School of the Arts, The Theatre School at DePaul University and the David Geffen School of Drama at Yale. He received an honorary doctorate from the University of Warwick. He was recently Co-Chair of Playwriting at the David Geffen School of Drama, where he remains on faculty. He is an associate at the Royal Shakespeare Company, London, and a member of the Academy of Motion Picture Arts and Sciences (Writers Branch).

Awoye Timpo (Director) is a Brooklyn-based Director and Producer. She recently directed Ngozi Anyanwu’s Leroy & Lucy at Steppenwolf. Her recent New York credits include The Swamp Dwellers by Wole Soyinka (TFANA), Syncing Ink by NSangou Njikam (Apollo Theater), Elyria by Deepa Purohit (Atlantic Theater), Wedding Band by Alice Childress (Theatre for a New Audience), In Old Age by Mfoniso Udofia (New York Theatre Workshop), Carnaval by Nikkole Salter (National Black Theatre), Good Grief by Ngozi Anyanwu (Vineyard Theatre and Audible) and The Homecoming Queen by Ngozi Anyanwu (Atlantic Theater Company). Regionally she has directed at the Huntington, Studio Theatre, Paradise Blue, Actors Theatre of Louisville, Berkeley Rep, Marin Theatre Company. Other projects include concert performances for independent artists as well as for the NBA, Ndebele Funeral (59E59, Edinburgh, South African Tour), “Black Picture Show” (Artists Space/Metrograph), and Bluebird Memories (Audible). Awoye is a Creative Arts Consultant for the African American Policy Forum and the Founding Producer of Classix, a collective of 5 artists created to explode the classical canon through an exploration of dramatic works by Black writers and Black performance history, theclassix.org .

Alana Arenas (First Lady, Second Wife, Miss Second, The Last One) joined the Steppenwolf Theatre Company ensemble in 2007. She most recently appeared in Steppenwolf’s world premiere of Purpose by Branden Jacobs-Jenkins in Chicago and on Broadway (Tony Award – Best Play). Alana also created the role of Pecola Breedlove for the Steppenwolf for Young Adults production of The Bluest Eye, which also played at the New Victory Theater Off-Broadway. Recent Steppenwolf appearances include: the Steppenwolf for Young Adults production of Monster, The Fundamentals, Marie Antoinette, Tribes, Belleville, Head of Passes, Good People, Three Sisters, The March, Man in Love, Middletown, The Hot L Baltimore, The Etiquette of Vigilance, The Brother/Sister Plays, The Tempest, The Crucible, Spare Change and The Sparrow Project. Broadway: Purpose. Other theatre credits include Disgraced (American Theater Company), The Arabian Nights (Lookingglass Theatre Company, Berkeley Repertory Theatre and Kansas City Repertory Theatre), Eyes (eta Creative Arts), SOST (MPAACT), WVON (Black Ensemble Theater) and Hecuba (Chicago Shakespeare Theater). Television and film credits include David Makes Man, Canal Street, Crisis, Boss, The Beast, Kabuku Rides and Lioness of Lisabi. She is originally from Miami, Florida, where she began her training at the New World School of the Arts. Alana holds a BFA from The Theatre School at DePaul University.

Glenn Davis (Marcus) is an actor, producer and Artistic Director of Steppenwolf Theatre Company, alongside Audrey Francis, where he has been an ensemble member since 2017. He most recently appeared in Steppenwolf’s world premiere of Purpose by Branden Jacobs-Jenkins in Chicago and on Broadway (Tony Award – Best Play, Tony nomination – Best Featured Actor). Other Steppenwolf credits include Downstate, The Christians, You Got Older, The Brother/Sister Plays, Head of Passes, King James (also Mark Taper Forum), Describe the Night. Broadway credits include: Purpose; Bengal Tiger at the Baghdad Zoo (also Kirk Douglas Theatre, Mark Taper Forum). Off-Broadway credits include Transfers (MCC Theatre), Wig Out! (Vineyard Theatre), Downstate (Playwrights Horizons, Outer Critics Circle Nomination) and King James(MTC). Other regional credits include Moscow x6 (Williamstown Theatre Festival). International credits include Downstate (National Theatre, UK); Edward II, The Winter’s Tale and As You Like It(Stratford Festival); Othello (The Shakespeare Company). Television credits include Billions, 24, The Unit, Jericho and The Good Wife. Glenn is an Artistic Associate at the Young Vic in London and at the Vineyard Theatre in New York. He is also a partner in Cast Iron Entertainment, a collective of artists consisting of Sterling K Brown, Brian Tyree Henry, Jon Michael Hill, Andre Holland and Tarell Alvin McCraney. Cast Iron is currently in residence at The Geffen Playhouse in Los Angeles. In 2021, Glenn founded The Chatham Grove Company along with his producing partner Tarell Alvin McCraney.

Jon Michael Hill (Nurse, Cori) joined the Steppenwolf Theatre Company ensemble in 2007. He most recently appeared in Steppenwolf’s world premiere of Purpose by Branden Jacobs-Jenkins in Chicago and on Broadway (Tony Award – Best Play, Tony nomination – Lead Actor). Steppenwolf Theatre Company: Leroy and Lucy, True West (also Galway Arts Festival), Pass Over, Constellations, Head of Passes, The Hot L Baltimore, The Tempest, Kafka on the Shore, The Unmentionables. Broadway: Purpose, Superior Donuts, Pass Over. Off-Broadway: The Refuge Plays (New York Theatre Workshop) Pass Over (Lincoln Center). Film: Pass Over, Widows, In The Radiant City, No Pay, Nudity. Television: A Man in Full (Netflix), Elementary (CBS), Detroit 1-8-7(ABC), Eastbound and Down (HBO), Law & Order: Special Victims Unit (NBC) and Person of Interest (CBS).

Esco Jouléy (Eli) won over audiences as “Sonya” in the Emmy-nominated FX series Dying for Sex, alongside Michelle Williams and Jenny Slate, and previously starred in the Sundance anthology series, State of the Union, opposite Patricia Clarkson and Brendan Gleeson. Esco recently returned to the stage for the sold-out, Off-Broadway run of Trophy Boys at MCC Theater. On stage, Esco also received rave reviews for their “magnetic” performance in New York Theater Workshop’s production of Merry Me, as well as their award-winning turn in Wolf Play.

Michael Potts (Henri ‘Mr. Mano’ Tamaño) is an award-winning actor whose prolific career on stage and screen has resonated with audiences for over four decades. Michael starred in the Broadway production of August Wilson’s The Piano Lesson (which he received an Outer Critics Circle nomination) and he then reprised his role of ‘Winning Boy’ to great acclaim in the Netflix adaptation, written and directed by Malcolm Washington opposite Samuel L. Jackson, Daniel Deadwyler and Corey Hawkins. Potts alongside the star studded cast were awarded the Tribute Award at the Gothams in 2024 for their cinematic artistry. Potts’ long line of screen credits include: Highest 2 Lowest (Apple TV, Spike Lee, dir.), Rustin (Netflix, George C. Wolfe, dir.), Ma Rainey’s Black Bottom (Netflix, Geore C. Wolfe, dir.), Change in the Air, Cicada and Here and Now. Next up on television, Potts will be seen co-starring in Courtney Kemp’s Nemesis for Netflix and in the new FOX medical drama Best Medicine from Liz Tuccillo, opposite Josh Charles. His other significant roles in television include: Law & Order, East New York, The First Lady, Prodigal Son, Madam Secretary, Law & Order SVU, Show Me a Hero, Gotham, True Detective, Damagesand ‘Brother Mouzone’ in The Wire. On stage, Michael’s career spans plays and musicals that endure in the lexicon of the American theater. Those include Jitney (NY Drama Critics Circle Special Citation), Grey Gardens, The Book of Mormon, The Iceman Cometh, The Prom, 1984 and Lennon. Off-Broadway he’s appeared in Richard II (Shakespeare in the Park), The America Play (Obie Award), Overtime (NY City Center), Mud River (Playwrights Horizons), Arms and the Man(Gramercy Theatre), Once Around the City (Second Stage), Twelfth Night (Shakespeare in the Park), The Mysteries (Classic Stage Company) and many more memorable turns.

Namir Smallwood (Officer, Brother 1) joined the Steppenwolf Theatre Company ensemble in 2017. He is currently starring in ensemble member Tracy Letts’s Bug on Broadway opposite ensemble member Carrie Coon. Steppenwolf: Mr. Wolf, You Will Get Sick, The Book of Grace, Seagull, Bug, True West, BLKS, Monster, Man In Love, The Hot L Baltimore, Last Night and the Night Before. Broadway: Pass Over, Bug. Off Broadway: Pipeline, Pass Over (Lincoln Center). Chicago: The Lost Boys of Sudan (Victory Gardens Theater); Charm (Northlight Theatre); The Grapes of Wrath (The Gift Theatre); East Texas Hot Links (Writers Theatre). Regional: Marin Theatre Company, Pillsbury House Theatre, Ten Thousand Things, Guthrie Theater. International: True West (Galway International Arts Festival). Television: Chicago Fire, Betrayal, Elementary, American Rust (Showtime/FreeVee); Power Book IV: Force (STARZ). Film: Rounding.

Accessibility:

As a commitment to make the Steppenwolf experience accessible to everyone, performances featuring American Sign Language Interpretation, Open Captioning and Audio Description are offered during the run of each STC production. Assistive listening devices (ALDs), large-print programs and braille programs are available for every performance and all our spaces are equipped with an induction hearing loop. Our building features wheelchair accessible seating and restrooms, push-button entrances, a courtesy wheelchair and all-gender restrooms, with accessible counter and table spaces at our bars. For additional information regarding accessibility, visit steppenwolf.org/access or e-mail [email protected].

Sponsor Information:

Windfall is supported in part by Conagra Brands Foundation, Laurents/Hatcher Foundation, and CNA. United Airlines is the Official and Exclusive Airline of Steppenwolf. Steppenwolf is also grateful for the significant season support from lead sponsors Allstate Insurance Company, Paul M. Angell Family Foundation, Bloomberg Philanthropies, Crown Family Philanthropies, Caroline and Keating Crown, Julius Frankel Foundation, Lefkofsky Family Foundation, Northern Trust, Anne and Don Phillips, John Hart and Carol Prins, Shubert Foundation, Inc, Walder Foundation, and Zell Family Foundation. Steppenwolf also acknowledges generous support from premier sponsors Anonymous, Andrew and Amy Bluhm, Michael and Cathy Brennan, Ann and Richard Carr, Chicago Community Trust, Conagra Brands Foundation, Rich and Margery Feitler, FROST CHICAGO, John D. and Catherine T. MacArthur Foundation, The Orlebeke Foundation, Polk Bros. Foundation, Sacks Family Foundation, Harold and Mimi Steinberg Charitable Trust, Thoma Bravo, Bryan Traubert and Penny Pritzker, and Vinci Restaurant. Steppenwolf also acknowledges support from the Illinois Arts Council and the City of Chicago Department of Cultural Affairs and Special Events.

About Steppenwolf Theatre Company:

Steppenwolf Theatre Company is the nation’s premier Ensemble Theater with 50 members who are among the top actors, playwrights and directors in the field. Thrilling, powerful, groundbreaking productions have made this theatre legendary. From the 1980 phenomenon of Balm in Gilead, to The Grapes of Wrath, August: Osage County, Downstate, The Brother/Sister Plays, and now, the 2025 Pulitzer Prize and Tony Award-winning Purpose, Steppenwolf Theatre has had a long-running and undeniable impact on American Theatre and Chicago’s cultural landscape. Founded in 1975 by Terry Kinney, Jeff Perry and Gary Sinise, Steppenwolf started as a group of young people in their teens and early 20s performing in the basement of a church. Today, the company’s artistic force remains rooted in the original vision of its founders: an artist-driven theatre, whose vitality is defined by its appetite for bold and innovative work. Every aspect of Steppenwolf is rooted in its Ensemble ethos, from the intergenerational artistic programming to the multi-genre performance series LookOut, to the nationally recognized work of Steppenwolf Education and Engagement which serves nearly 15,000 teens annually. While grounded in the Chicago community, more than 40 original Steppenwolf productions have enjoyed success nationally and internationally, including Broadway, Off-Broadway, London, Sydney, Galway and Dublin. Steppenwolf also holds accolades that include the National Medal of Arts, 14 Tony Awards, two Pulitzer Prize-winning commissions and more. Led by Artistic Directors Glenn Davis and Audrey Francis, Executive Director E. Brooke Flanagan and Board of Trustees Chair Keating Crown — Steppenwolf continually redefines the boundaries of live theater and pushes the limits of acting and performance.

Steppenwolf’s Mission: Steppenwolf strives to create thrilling, courageous and provocative art in a thoughtful and inclusive environment. We succeed when we disrupt your routine with experiences that spark curiosity, empathy and joy. We invite you to join our ensemble as we navigate, together, our complex world.

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