The Brooklyn Rail

Nonprofits rarely exist without donors. These gift-givers do more than keep the lights on—they finance critical changes. But not all of them easily open their wallets.

After over a decade fundraising for the ACLU, Matthew Freeman is well aware of this reality. In his new play, The Ask, he examines this relationship through Greta (Betsy Aidem) and Tanner (Colleen Litchfield)—one, a wealthy Upper West Sider, the other, a nonbinary progressive hire at the ACLU. When Tanner asks for funds, the odd pair find themselves in a “pressure-cooker” while trying to see eye-to-eye.

The Ask explores how far we go to understand each other—and what we give up to get what we need.

Kenneal Patterson (Rail): You’re an award-winning playwright by night—and ACLU’s associate director of giving by day. How did the 9-to-5 grind turn into inspiration for The Ask?

Matthew Freeman: I’ve worked for the ACLU for thirteen years. I’ve always had to work to make a living. I don’t come from wealthy people—my mom is a teacher. My dad is an Episcopal priest.

But writing’s my passion and I’ve been writing for a long time. I never wanted to write about my day job. For most of us in the arts, I think there’s sort of an allergy to including the day job—because it’s the thing you’re trying to leave or working in opposition to. Yet I got fascinated by a particular dynamic going on at the ACLU.

Rail: This dynamic revolves around a wealthy donor and the young employee who asks for her money. They’re very different.

Freeman: One of the things at work in the play is the generational divide. There’s a younger, nonbinary fundraiser who was recently hired. All of a sudden, this young person is in a role that they may not have been before, and they must come to a more experienced, older philanthropist and ask for money.

In every walk of the progressive world, those groups are in some tension. There’s not just a money imbalance, there’s also this feeling of “you don’t understand me,” or “I don’t understand you,” even though everybody in that room is probably going to vote the same way.

Rail: Especially as the election approaches, these divisions are resounding across the country. How do they play out within your office?

Freeman: People support the ACLU due to its commitment to constitutional protection. Through the First Amendment, you defend even the worst people’s rights to speak. Recently, the ACLU was involved in a case with the NRA. Some people were very upset. Other people said, well, that’s what the ACLU does. The ACLU defends an idea more than an individual or group.

But are you so focused on being everything to everyone that you’ve lost your core identity as an organization?

Rail: For generations, young people have asked similar questions and resisted the status quo. But their environments often discourage this kind of skepticism. Is Tanner an example of this paradox?

Freeman: Tanner is doing their job. They aren’t trying to throw in their own perspective. As a fundraiser, you want people to have an authentic experience with you. But you’re there to represent the organization and ask for a gift, and there’s an artificiality to it. A lot of what Tanner may or may not believe gets oppressed by the situation they’re in.

Greta has freedom to express herself. There’s an illusion that Tanner is an equal person to have an argument with. But that’s actually not the case. Tanner cannot do that, because they need something.

Rail: The play seems to ask how far we’ll go for something we need. But the “greater good” can come with costs and consequences.

Freeman: At the ACLU—and the nonprofit sector in general—some donors will say things that offend you. And because they have a lot of money, sometimes the expectation is that you just put up with their microaggression. More and more, there’s this feeling of: maybe we don’t have to sublimate in order to put up with that. Maybe if I’m a young trans person and someone deadnames me in a meeting, maybe I can get up and walk out.

Rail: What are these donors like in real life?

Freeman: We’re often dealing with people that are not villainous at all. They probably have really good values and they mean well. Many of them have been feminists who fought for women’s rights for years.

Now they’re older, and they have money, and when asked for their money, they have strong opinions. They’re not necessarily bad people, but in those environments, they might be accidental bullies.

Rail: At the ACLU, you’re often working to maintain these relationships.

Freeman: We should view people who are charitable with charity. It’s not my inclination to look at someone who’s earned a certain amount of money in their life and wants to give it away and question their motives.

No one’s motives are one hundred percent pure on this earth. Even when you ask for money, you have great intentions—but you also have a job, and you want to not lose that job, and you want to use that job to pay for beer and you want to use that job to pay for rent. Donors are the same way. They care about the organization, but they have certain reasons to give.

We want nonprofits to exist. But they only exist because of this kind of giving. So unfortunately, there’s an inherent kind of power imbalance because of our need.

Rail: Money will always be a touchy topic, so there’s a sense of discomfort inherent in the show. Will the show ask something of us—to question our own beliefs or entitlement?

Freeman: I like plays that give you a little sense of “ouch.” It’s the pleasure of watching a car crash. There are moments where the dynamics definitely shift, or how you feel about the characters you might agree with will be challenged.

Rail: Who are you aiming to lure in?

Freeman: Hopefully everyone in New York!

It’s a bloodbath out there—theaters are closing. It’s a hell of a thing to fall in love with something that’s slowly falling off the face of the earth. It’s harder and harder to get people to come out. But theater is important. It’s about thinking about one another and looking outside of yourself.

I’m hoping that if there are audiences out there to be found, they will find us.