Meet Rabbi Jenna, Jewish Cubs Fan of the Week

by Samuel Milligan / June 3, 2026

The GatherDC blog strives to present a holistic portrait of the DMV’s Jewish community, sharing a wide variety of Jewish voices and perspectives. If you have a 20- or 30-something to nominate as our Jewish Person of the Week or for a Spotted in Jewish DMV feature, please email us!

Rabbi Jenna and I sit down at Yerevan. In the cool shelter of the air conditioning, we chat about their professional journey to Sixth & I, the overlap between sports fandom and religious belonging, where to get lunch, and our responsibilities as future Jewish ancestors.

Jenna and their dog.

Samuel: What brought you to the DMV?

Jenna: I grew up in Chicago, in a family that did Judaism but…Judaism wasn’t a deep part of our life story, so it wasn’t an obvious thing that I would go on and become a rabbi. When I was in high school, I got involved in a youth group, and I was like: Whoa, Judaism is this thing we can build, we can create, it’s fun, it can bring people in, it can meet people where they’re at. Around the same time, I kind of accidentally stumbled into a mayoral campaign office. The energy and sense of passion and possibility that came from local politics felt deeply spiritual to me, and I was like: I want to move to DC to do politics. So I came here for college at American University! From the minute I stepped off the plane in DC, I [felt like] this is where I want to be for the rest of my life. I’ve been here since 2013, with some gaps in between. DC is deeply, deeply home.

Samuel: What’s keeping you here?

Jenna: It’s funny – the thing that brought me here and made me fall in love with this city is not what keeps me here. The city has changed tremendously, and I’ve thought often in the last year about what it means to love the city and find it home when that feels really hard. We’re watching gentrification, occupation, all these things. But also, I love bookstores. I love museums. I love food. And this is such an amazing city to hear stories through books, through food, through museums. There’s a lot here.

Rabbi Jenna at Simchat Torah.

Samuel: What’s your ideal museum, bookstore, meal trio?

Jenna: I’m going to Purple Patch for lunch. I’m going to the National Museum of Women in the Arts or the Postal Museum. And then I’m going either to Lost City Books or Capitol Hill Books. 

Samuel: You’re an Associate Rabbi at Sixth & I. How do you approach being the rabbi for a community like that?

Jenna: Something that I love about being a rabbi and hold with so much weight and humility is that people trust me with the deepest stuff they’re sitting with right now. Like, I need you to help me get through the next week, I need you to help me figure out this crisis that I’m grappling with. It’s so immediate and holy. There’s this person sitting in front of me and my job is to see their holiness, to see their soul, and to accompany them in this really amazing way. I feel like I have been entrusted with a lineage that has gone way before me and will, God-willing, continue to go way after me. 

Sixth & I staff holding Pride flags.

So, how do I sit in the deep immediacy of the person in front of me while also thinking about the future? When I think of myself, as a Queer and trans person…there are not many models of trans rabbis at big congregations and communities. So many rabbis before me have opened doors so that I could walk through, so inherent in my identity is to be a door opener for other people and the people who will come after me. I would love to see a universe where being a trans rabbi is not a big [deal]. There are days where I don’t want to be a “trans rabbi,” I want to be a rabbi. My identity is what shapes who I am and helps me understand the world, but I’m a rabbi for the Jewish people. I serve our tradition, I serve the Jewish people, I serve God. I’m a rabbi. That’s the project, and it’s really cool.

What made me fall in love with Judaism – and I fell in love with Judaism before I had the language to articulate that I was trans – is that Judaism, if done right, is one of the most powerful tools to help you access what’s inside of yourself that is hard to put into words and make sense of. What is your inner world? Judaism, and the wisdom of our tradition, can help you access that. The silence and space and sound of prayer, the community, the wisdom: all of those are tools of access. When we expand attentive Judaism to reach those in the margins, those in the center who Judaism has always been “for” are just made stronger. I approach Judaism like: What do we get to do because the doors are open wide? Every single person is a shaper of our tradition. Judaism is a collective project.

Samuel: What else is feeling alive for you Jewishly right now? 

Jenna: I’m really interested in the ways that the story around trauma and antisemitism and fear has distracted us from building a Judaism that is loving and creative and meaningful and joyous. I’m interested in the question of: What is a Judaism that recognizes Jewish stories and histories of trauma, but is shaped by possibility, imagination, joy, and love instead of that trauma? How do we build that Judaism and a Judaism that will survive into the future? How do we build a Judaism that can hold the complexity of everything we bring to it? Our tradition has survived destruction, displacement, plagues, the Holocaust, and our Jewish tradition has held moments of joy, confusion, grief, and deep euphoria. What does it mean to let ourselves fall into the beauty and wisdom and possibility within our tradition? 

I’ve been spending a lot of time over the last two years learning what Jewish tradition has to say about imagination. I have a dear friend, Becca Leviss, who writes about Judeo-futurism. She invites us to think about not just what we’re doing next week, a year from now, five years from now, but also what Judaism looks like in fifty and a hundred years from now. We’re future ancestors. What is the foundation of Judaism that we’re creating for our [descendants]? I’m spending a lot of time thinking about both what we can learn from our ancestors and how we can be good ancestors. 

Rabbi Jenna holds a baseball at a game.Samuel: Okay, real big topic shift here. How do Judaism and baseball overlap for you?

Jenna: In third grade, my Mom and I were at Game Six of the 2003 National League Championship Series. The Cubs were five outs away from the World Series…that’s the Steve Bartman game. I knew I was a Cubs fan, I knew I was excited about the Cubs, but I didn’t understand the weight of what I was stepping into. My Mom turns to me and says: This is unbelievable, you’re too young to understand, but you’re about to witness history. And then Steve Bartman happens and the entire stadium just starts booing and chanting [Chicagoan expletives]. And it’s clear [that the Cubs will lose], and the stadium just went silent.

As I reflect on it later, I think a lot about how that moment taught me about what it means to be part of a spiritual community. Like, that was the first collective spiritual experience I ever had, and I think a lot about the idea of collective effervescence. That’s the idea that we are collectively having an experience, and the experience might be different for everyone, but there’s something in that collective…and that is Judaism. 

And, that is baseball. To understand sports is to understand the project that religion is doing. Being a baseball fan gives me the tools to be a better rabbi. So much of the experience of sports is reckoning with history and legacy and tradition. There’s insiders, there’s people who know every rule, and there’s people who are just there at Wrigley for a beer on a nice day. That’s a metaphor for the Jewish people, too. For some people, the language of something greater than yourself is God. For other people, it’s many other things. I think God is the experience that happens in deep connection between people. 

Jenna speaking into a loudspeaker.

Samuel: Okay, a couple quick ones to close. How do you feel about the Pope being a White Sox fan?

Jenna: It continues to buffer my stance that sports are one of the most powerful tools to access God.

Samuel: You’re hosting Shabbat dinner and can invite any three people. Who are you bringing?

Jenna: There’s a meal where I want to understand what it means to be a person in the world. For that meal, it’s Adrienne Maree Brown, Martin Buber, and Moses. There’s another version of the meal where I’d love to have dinner with Theo Epstein, Anthony Rizzo, and some other key members of the 2016 World Series Cubs team. And there’s a third version where it is younger versions of myself and people I love, hosted by our grown-up selves.

Samuel: Last one. Finish the sentence: When Jews of the DMV gather…

Jenna: Something transformative happens. It creates a container to combat loneliness. When Jews gather, we see each other, we see ourselves, and we learn a little about the world we’re in, which makes it less hard to hope.

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