At the Vatican with Chicago’s mayor, a rabbi gave Pope Leo a White Sox kippah
Rabbi Lizzi Heydemann said she thanked the pontiff for recognizing the humanity of both Israelis and Palestinians
A delegation of Chicago faith leaders meet with Pope Leo XIV on May 28, 2026. (Courtesy of Simone Risoluti/Vatican Media)
(JTA) — Lizzi Heydemann didn’t plan what she was going to say to Pope Leo XIV.
But when the Chicago rabbi found herself face-to-face with the new pontiff during a Vatican visit alongside a delegation of Chicago leaders, she thanked him for the way he has spoken about the war in Gaza.
“I said, you know, it’s been a hard time over these past two years to be a rabbi, but I want to thank you for, in the midst of conflict, holding the humanity of everyone involved in the conflict,” Heydemann recounted.
Leo, the first American pope and a native of Chicago’s South Side, repeatedly advocated after his election last year for the release of the Israeli hostages as well as a ceasefire in the war in Gaza, which he has referred to as “vengeance” and “barbarity.” The comments angered some Jewish leaders who have interpreted them as unfairly targeting Israel, but for others including Heydemann, they have offered a template for how to criticize the war.
“You may be anti-war, but I do not hear you denouncing or degrading people,” Heydemann said she told Leo. “Thank you for holding the humanity of Israelis and Palestinians in the same breath and the same thought. It’s not something that is modeled very often.”
She added, “He seemed grateful, and like he knew exactly what I was talking about.”
Heydemann, the founder and leader of Mishkan Chicago, an independent Jewish spiritual community, had been invited by Chicago Mayor Brandon Johnson to join a delegation of civic, business and faith leaders traveling to Rome last week. (Johnson has been a vocal critic of Israel who has drawn criticism himself from some Jewish leaders in Chicago.) She said she was the only rabbi to take part in the trip.
As she waited for the pope to enter a room where the delegation was assembled on Thursday, Heydemann said she began weeping.
“What I reflected on is that he, maybe more than anyone in the world, is a religious leader with the world’s eyes on him,” Heydemann said. “He is beloved and critiqued constantly, and every rabbi in America has had a little taste over the last few years of that weight.”
While the interaction carried an unexpected emotional weight for Heydemann, it also came with a distinctive Jewish Chicago touch: a White Sox-themed kippah.
She said she included the kippah, which featured the Chicago White Sox logo on the exterior as well as a pomegranate on the inside, in a chest of Chicago-themed gifts presented to the pope on Thursday during the visit as a nod to his lifelong devotion to the baseball team.
“We thought that would be a sweet point connection between me and the pope,” Heydemann said, adding that the pontiff’s typical white zucchetto looks “awfully like a kippah.”
“It brings us all joy to imagine that after a long day at work wearing the cream-colored one that matches his robes, maybe at the end of the day he’ll switch it out for a jersey material, White Sox kippah, and thinks fondly of sweet home Chicago, and the Jewish spiritual community gave it to him,” Heydemann added.
A list of gifts that circulated in local media included another piece of Jewish paraphernalia: a tote bag with the words “Resisting tyrants since Pharaoh.” That’s a catchphrase from T’ruah, the rabbinic human rights group where Heydemann has been on the board. But the rabbi said the inclusion was an error: She was carrying the bag, not giving it to Leo.
Looking back on the meeting with the pope, Heydemann said her experience reflected a broader conviction about “building bridges, even in the presence of difference.”
“There’s too much at stake in our world for us to not be continuing to be in relationship with one another in the presence of differences,” Heydemann said.
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