Because It’s True: Courage, Conviction, and Being an Unapologetic Jew — with Shabbos Kestenbaum

I’ve admired Shabbos Kestenbaum for a while.There are obvious reasons for this. He sued Harvard. He has become one of the most recognizable young Jewish voices in America. He is willing to walk onto stages where neither Jews nor Israel are especially welcome, wearing a yarmulke, and say plainly what he believes.But that isn’t really what I admire most about him.What I admire is his clarity. Shabbos seems to possess something increasingly rare: a willingness to decide what is true before deciding what it will cost him to say it.At one point in our conversation, I asked him where he gets his courage.He resisted the question.He doesn’t experience himself as courageous. When it comes to Israel, the Jewish people, and the 3,000-year-old story he inherited, he doesn’t feel that he is bravely defending some controversial position. He believes these things are true. He feels profoundly fortunate to belong to this story. And standing up for it is, as he puts it, simply “what you do.”I found that answer striking, because it gets at something deeper than courage.Courage suggests overcoming fear. Shabbos was describing something that comes before fear: knowing who you are.That became, for me, the thread running through our conversation.We spoke about his unusual childhood and Jewish upbringing; Harvard and October 8th; Israel; Kiddush Hashem; the story of Yonah; and what Jewish resistance actually looks like. Sometimes resistance means taking Harvard to court. But it can also mean wearing a Magen David. Dating Jewish. Learning Torah. Building a Jewish home. Becoming, quietly and deliberately, a little more Jewish than you were yesterday.And beneath all of it was a question I kept returning to: What happens when a person knows who he is deeply enough that he no longer needs the world’s permission to be it?This is a conversation about courage, although Shabbos might reject the word. It is a conversation about conviction, responsibility, Jewish pride, and the peculiar freedom that comes from knowing that your life belongs to a story that began long before you and, God willing, will continue long after you.