Ep. 562: Why Is Yom Kippur the Holiest Day of the Year? episode artwork

EPISODE · Sep 29, 2025 · 1H 9M

Ep. 562: Why Is Yom Kippur the Holiest Day of the Year?

from MyLife: Chassidus Applied · host Rabbi Simon Jacobson

Rabbi Jacobson will discuss the following topics: Vav Tishrei Any recollections of Vav Tishrei 5725? Why did the Rebbe honor his mother by explaining Rashi’s commentary on the parsha? Can you tell a story about the Rebbe’s mother to inspire us as we head into Yom Kippur? Why is this the holiest day of the year? What is the personal significance of this day? Does G-d need to “atone” for suffering He has caused us? Why lekach? Is Yom Kippur a joyous day? Why do we fast? Why is Yom Haki-purim compared to Purim? What is the connection to a lottery? Why two goats? Should we fight our enemies or transform them? What are some suggestions the Rebbe made to help win the Yom Kippur war? Can we do some of those things this Yom Kippur to win today’s war? Kaporos Kol Nidrei Ki Hinei KaChomer Why do we say in Avinu Malkeinu that “we have no accomplishments”? Why were the ten martyrs killed? V’tiher Rabbi Yishmael How should we react to the embarrassing conflicts in our own shul? Chassidus Applied to Yom Kippur  Yom Kippur Prayers How should we react to countries like England, France and Canada declaring a Palestinian state? Can we expect peace in Israel if we have no peace in our communities? 

Rabbi Jacobson will discuss the following topics: Vav Tishrei Any recollections of Vav Tishrei 5725? Why did the Rebbe honor his mother by explaining Rashi’s commentary on the parsha? Can you tell a story about the Rebbe’s mother to inspire us as we head into Yom Kippur? Why is this the holiest day of the year? What is the personal significance of this day? Does G-d need to “atone” for suffering He has caused us? Why lekach? Is Yom Kippur a joyous day? Why do we fast? Why is Yom Haki-purim compared to Purim? What is the connection to a lottery? Why two goats? Should we fight our enemies or transform them? What are some suggestions the Rebbe made to help win the Yom Kippur war? Can we do some of those things this Yom Kippur to win today’s war? Kaporos Kol Nidrei Ki Hinei KaChomer Why do we say in Avinu Malkeinu that “we have no accomplishments”? Why were the ten martyrs killed? V’tiher Rabbi Yishmael How should we react to the embarrassing conflicts in our own shul? Chassidus Applied to Yom Kippur  Yom Kippur Prayers How should we react to countries like England, France and Canada declaring a Palestinian state? Can we expect peace in Israel if we have no peace in our communities?

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Ep. 562: Why Is Yom Kippur the Holiest Day of the Year?

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This episode is 1 hour and 9 minutes long.

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This episode was published on September 29, 2025.

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Rabbi Jacobson will discuss the following topics: Vav Tishrei Any recollections of Vav Tishrei 5725? Why did the Rebbe honor his mother by explaining Rashi’s commentary on the parsha? Can you tell a story about the Rebbe’s mother to inspire us as we...

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