Why Did Rabbi Yehuda Hanasi Cry Over the Teshuvah of Rabbi Eliezer ben Durdaya
Brooklyn Torah Gazette | November 24, 2025
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Why Did Rabbi Yehuda Hanasi Cry Over the Teshuvah of Rabbi Eliezer ben Durdaya

Brooklyn Torah Gazette | December 07, 2025

A Chassid once came to the Chiddushe Harim (Rabbi Yitzchak Meir Alter, the first Gerer Rebbe) and asked the following question. The Gemarah tells us that there was someone who sinned greatly and one day suddenly aroused to do Teshuva. His name was Rabbi Eliezer ben Durdaya. He sat on the ground and cried so bitterly from regret that he passed out and died.

The Gemara tells us that Rebbi Yehuda Hanasi cried and said, “there are those that can merit their Olam Haba in an hour.” (I.e. Rabbi Elazar ben Durdaya had done such sincere Teshuva the last hour of his life that he merited Olam Haba.)

The Chassid asked, how is it possible that a Rasha that sinned his whole life should merit Olam Habba just like the Rebbe who has spent his whole life in Torah, Tefillah and Avodas Hashem? Secondly, if Rabbi Eliezer ben Durdaya did Teshuva and merited Olam Haba why did Rabbi Yehuda Hanasi cry? He should have rejoiced?

The Rebbe answered with the following story. There was a wagon driver who was on his travels in the cold winter and was traveling through the snow. He heard a strange noise from outside. He stopped his wagon and went outside. He saw a Jew on the ground so cold and frozen, literally on the verge of dying. He carried the man in to his wagon and started warming him up. He rubbed snow on his ears to help him warm up, he covered him with dry blankets and slowly the man started warming up. No doubt the wagon driver had saved the man’s life.

There was an uproar in Heaven. The Gemarah says that a person who saves someone’s life is as if they kept up the whole world. No doubt this man was worthy of Olam Haba. On the other hand, he wasn’t a big Tzaddik and if he dies in another thirty or forty years he will have done enough sins that he wouldn’t be able to receive the reward of this great Mitzva.

In Heaven they decided to send Eliyahu Hanavi to ask the man what he prefers? To die now and go straight in to Olam Haba or to stay alive. The man decided he wants to die straight away. He asked permission to be able to bid farewell from his family and after that he passed away.

As promised he came to Heaven and it was ruled that he deserves Olam Haba. However, the man wasn’t very learned so in Heaven they weren’t sure that he would enjoy Gan Eden. So, they asked him what he would like for his reward? The man answered that he worked for a living as a wagon driver and many of his travels were on stony roads. Therefore, if he can choose, he would like a golden comfortable carriage, six powerful white horses and a smooth track to be able to ride his horses on. The man was granted his wish and drove off on a track that will never end forever.

What a pity on that man, said the Rebbe. He got Olam Haba but what was his Olam Haba? What a waste! That is what Rabbi Yehuda Hanasi cried. A person who had no connection to spirituality and does Teshuva the last moments of their life, they may earn Olam Haba but what will they enjoy as a reward in Olam Haba? That is what Rabbi Yehuda Hanasi cried, that he acquired his Olam Haba in an hour, but how sad, what his Olam Haba might be.

No doubt that for coming to Shul in such challenging times we will receive reward. But what reward will we receive? In the Yehi Ratzon before we say Tehillim we say that in the same way we said Tehillim in this world, so we should merit to be able to say praises of Hashem in Olam Haba. So, if we get a Siddur or Tehillim in Olam Haba, what will we do with it? We won’t understand a word we are saying, we will find it monotonous, we won’t have our neighbor from Shul to chat with. That won’t be fun.

So, Hashem will prepare us a big hall full of laid tables. There will be a Kiddush beyond our dreams. All sorts of cakes, pastries, crackers, herrings, cholents, kishka, gala, all different sorts of meats, cold cuts and kugels , drinks, whiskies, chocolates and an appetite that never ends forever, so we can eat nonstop forever. Is that the Olam Haba we are really waiting for, asked the Rebbe who has spent his whole life in Torah, Tefillah and Avodas Hashem?

Reprinted from the Parshas Chayei Sarah 5786 email of Rabbi Dovid Caro’s Inspired by a Story.

A Chassid once came to the Chiddushe Harim (Rabbi Yitzchak Meir Alter, the first Gerer Rebbe) and asked the following question. The Gemarah tells us that there was someone who sinned greatly and one day suddenly aroused to do Teshuva. His name was Rabbi Eliezer ben Durdaya. He sat on the ground and cried so bitterly from regret that he passed out and died.

The Gemara tells us that Rebbi Yehuda Hanasi cried and said, “there are those that can merit their Olam Haba in an hour.” (I.e. Rabbi Elazar ben Durdaya had done such sincere Teshuva the last hour of his life that he merited Olam Haba.)

The Chassid asked, how is it possible that a Rasha that sinned his whole life should merit Olam Habba just like the Rebbe who has spent his whole life in Torah, Tefillah and Avodas Hashem? Secondly, if Rabbi Eliezer ben Durdaya did Teshuva and merited Olam Haba why did Rabbi Yehuda Hanasi cry? He should have rejoiced?

The Rebbe answered with the following story. There was a wagon driver who was on his travels in the cold winter and was traveling through the snow. He heard a strange noise from outside. He stopped his wagon and went outside. He saw a Jew on the ground so cold and frozen, literally on the verge of dying. He carried the man in to his wagon and started warming him up. He rubbed snow on his ears to help him warm up, he covered him with dry blankets and slowly the man started warming up. No doubt the wagon driver had saved the man’s life.

There was an uproar in Heaven. The Gemarah says that a person who saves someone’s life is as if they kept up the whole world. No doubt this man was worthy of Olam Haba. On the other hand, he wasn’t a big Tzaddik and if he dies in another thirty or forty years he will have done enough sins that he wouldn’t be able to receive the reward of this great Mitzva.

In Heaven they decided to send Eliyahu Hanavi to ask the man what he prefers? To die now and go straight in to Olam Haba or to stay alive. The man decided he wants to die straight away. He asked permission to be able to bid farewell from his family and after that he passed away.

As promised he came to Heaven and it was ruled that he deserves Olam Haba. However, the man wasn’t very learned so in Heaven they weren’t sure that he would enjoy Gan Eden. So, they asked him what he would like for his reward? The man answered that he worked for a living as a wagon driver and many of his travels were on stony roads. Therefore, if he can choose, he would like a golden comfortable carriage, six powerful white horses and a smooth track to be able to ride his horses on. The man was granted his wish and drove off on a track that will never end forever.

What a pity on that man, said the Rebbe. He got Olam Haba but what was his Olam Haba? What a waste! That is what Rabbi Yehuda Hanasi cried. A person who had no connection to spirituality and does Teshuva the last moments of their life, they may earn Olam Haba but what will they enjoy as a reward in Olam Haba? That is what Rabbi Yehuda Hanasi cried, that he acquired his Olam Haba in an hour, but how sad, what his Olam Haba might be.

No doubt that for coming to Shul in such challenging times we will receive reward. But what reward will we receive? In the Yehi Ratzon before we say Tehillim we say that in the same way we said Tehillim in this world, so we should merit to be able to say praises of Hashem in Olam Haba. So, if we get a Siddur or Tehillim in Olam Haba, what will we do with it? We won’t understand a word we are saying, we will find it monotonous, we won’t have our neighbor from Shul to chat with. That won’t be fun.

So, Hashem will prepare us a big hall full of laid tables. There will be a Kiddush beyond our dreams. All sorts of cakes, pastries, crackers, herrings, cholents, kishka, gala, all different sorts of meats, cold cuts and kugels , drinks, whiskies, chocolates and an appetite that never ends forever, so we can eat nonstop forever. Is that the Olam Haba we are really waiting for, asked the Rebbe who has spent his whole life in Torah, Tefillah and Avodas Hashem?

Reprinted from the Parshas Chayei Sarah 5786 email of Rabbi Dovid Caro’s Inspired by a Story.

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