Ask a Jew

Cry Me a River to the Sea


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Shabbos Kestenbaum is probably the most famous Jewish Harvard grad since Natalie Portman. You may know him as a former Bernie Bro and divinity student who went on to sue Harvard for discrimination, speak at the Republican National Convention, and accompany President Trump to the gravesite of the Lubavitcher Rebbe. We talk about what to do with all this sweet, sweet Jewish money, where Israel goes wrong on messaging, what Shabbos saw at the Gaza humanitarian aid crossing, and much more.

Also:

* Whats’s the deal with his name? (ask his siblings “Independence” and “India”)

* From the Harvard Divinity School to yelling on Piers Morgan

* Shabbos’s mom unfollowed him on X

* "In a place where there are no people, strive to be a person"

* History didn’t start on October 7…Shabbos on Harvard antisemitism in 2022 in Aish.com

* Lots of students agree with Shabbos….quietly

* The watermelon Yamulke crowd

* How to combat antisemitism (hint: not more Holocaust studies)

* Why the ADL stopped inviting him to meetings, but he still respects Jonathan Greenblatt (so do we by the way, in case you want to invite us to speak)

* GIVE THE MONEY TO STUDENTS

* Big Tent, Little Tent, Chabad and Hillel

* Ladies, he’s single - a sharpt turn toward dating and the Marvel Universe

* Why does Israel suck at messaging? Unclear, but here’s what to do

* A very interesting meeting at the Gaza aid crossing



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