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Since its original 2020 Off-Broadway debut was postponed until 2024 by the Covid-19 Pandemic, Itamar Moses’ “The Ally” has likely ripened in its effectiveness. Not because the play has changed, but because the world has.

A 2025 Pulitzer finalist, now in its Midwest premier at Theater Wit, it revolves around the ambivalence of Jewish college writing professor Asaf (Jordan Lane Shappell in a sterling performance) as his Black student Baron (DeVaughn Asante Loman) asks him to sign-on to a manifesto decrying the killing of his cousin by campus police.

Initially sympathetic to this cause, Asaf becomes reluctant to sign on, even though he agrees with its indictment of systemic injustice against people of color. His sticking points? A section ties in charges against Israel for operating an apartheid state vis a vis Gaza, condemning what it describes as policies of genocide against Palestinian people—even more timely topics today given current political discourse and a war in Iran.

Through a fast-paced dialog, the playwright puts on stage detailed explications of points of view that are known to trigger family battles during holiday dinners, or have become verboten altogether in the interests of peaceful coexistence. There seems nowhere safe to listen to opposing positions.

But not so on the stage in “The Ally.” Expertly directed by Jeremy Weschler, who has led a stellar cast to precision delivery with impeccable timing, this production is remarkable simply on the basis of how well rehearsed the performers seem to be in a complicated, granular script.

In publicizing the play, Weschler says, "Before October 7th, I — like a lot of American Jews on the left — held two ideas at once: that Israel was a haven and that the occupation was wrong. Itamar Moses saw, honestly before I did, that those two ideas were becoming impossible to hold simultaneously. But there are always two ways to answer the question ‘What do I believe?': what do I think, and what do I feel? Where we land on that spectrum is a constant negotiation between ourselves and the world around us. What ‘The Ally’ asks — what it really demands — is that we face that negotiation honestly. Can we be good people when our hearts and our heads aren't aligned?”

In the main setting, a library meeting room, impassioned, invested characters put forth their positions. Most have direct experience of that about which they speak. This is both enthralling and compelling, emotionally engaging at the peak moments, as we hear them passionately expounded their positions. Each felt equally compelling, even though they are often diametrically opposed.

Moses is a skillful playwright. He has wrapped the political discourse in a romantic drama, the relationship between Asaf and his wife Gwen (K Chinthana Sotakoun), a faculty member who is of Asian descent. The play opens with a skillful rendering of a couple tentatively probing and challenging each other in a very realistic way.

That scene changes from the living room to campus. Having heard from Baron, and as Asaf tussles with signing the manifesto, the playwright ups the stakes. Palestinian student Farid, (Arman Ghaeini) and his “ally” (a recurring theme) Jewish student Rachel (Mira Kessler), ask Asaf to support the appearance of a noted speaker who questions Israel’s actions in Gaza. Asaf agrees to be their student group sponsor authorizing the speaker.

When Reuven (Evan Ozer) a Jewish PhD student, discovers this, he barges in on Asaf to lay out all the reasons this speaker should not be allowed to address the student body. While Israel may seem brutal at home, he contends, one must think of it in context: Israel is surrounded by middle eastern states that oppose its very existence. Any presentation that might undermine Israel’s welfare should be banned.

Moses’s script is designed to give each of the characters a long moment in the spotlight. For relief he reverts to scenes between Asaf and Gwen. Each of the characters is articulate and brilliant. When Reuven makes his case for Israel, for example, he also recounts accurately the arguments of its opposition as he dispels them.

Most intriguing, and emotionally compelling, is Farid. In his first few appearances he is reticent, retreating, polite. But when the playwright offers him his featured monolog, Farid expresses the suffering of Palestinians, and then, moves to a vehement display of their anger. Arman Ghaeini runs away with this scene, engendering from me empathy and even catharsis. When have I heard this expressed? Never before.

Likewise for Baron, who is generally rather laconic. As the debates on stage progress over the connections between the Israel-Palestinian conflict and racial injustice in the U.S., Baron has his moment for a passionate peroration, and Loman's delivery is powerful.

Throughout, Asaf remains the buffeted everyman, conscious of the warring sympathies within himself, and unable to resolve them. The play has some weaknesses as a drama—an old flame now community activist Nikea (Sharyon Culberson) appears, igniting jealousy in Gwen. But as an expression of the struggle we experience societally, through the vehicle of the conflicted Asaf—that weakness doesn’t hamper the impact and value of “The Ally.”

It is worth noting “The Ally” was written before the Hamas strike against Israel in October 2023. That event killed 1,200 and saw 251 taken hostage. In its subsequent defense, Israel has retaliated and sought to destroy Hamas, killing 73,000 Palestinians and isolating Gaza. Also noteworthy: this Chicago production is only the second staging of the work. Perhaps its incendiary subject makes producers skittish.

But “The Ally” has a heightened immediacy today, and should be seen. Highly recommended, “The Ally” runs through May 2, 2026 at Theater Wit in Chicago.

Extended through May 17th!

This review is proudly shared with our friends at www.TheatreInChicago.com.