Right before Kol Nidrei, we make a startling declaration: we permit ourselves to daven together with the transgressors. Chazal go even further and teach that a communal fast without the sinners of Israel is not considered a true fast.
Why?
Because Yom Kippur is not meant to become a private religious experience. The Navi Yeshayahu tells us that if our fasting causes us to turn inward and stop seeing the hungry, the wandering, and the broken, then we have misunderstood what the day is supposed to accomplish.
In this shiur, delivered in Tomer Devorah, Rav Burg explores the deeper meaning of Yom Kippur as a day when the walls between Jews begin to fall away, culminating in Neilah and the revelation of the Yechidah, the place where we are all one.
At the center is the remarkable story of Rabbi Ronnie Greenwald, who spent much of Yom Kippur sitting in a hotel lobby with a group of struggling young Jews. He did not lecture them or try to win an argument. He simply stayed with them.
He gave them his Yom Kippur.
And in doing so, he may have shown us what Yom Kippur is really about.