The Wisdom of the Chutzpahdik Student’s Teacher
Shabbos Stories | March 08, 2026
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The Wisdom of the Chutzpahdik Student’s Teacher

Shabbos Stories | March 09, 2026

Rav Zelig Pliskin

Rav Zelig Pliskin writes that boldness and brazenness are two sides of the same coin. One leads to great acts of courage, and the other can cause great harm, but both can be turned to do good. Chutzpah and courage have certain elements in common. But they are on the opposite ends of the scale. Courage is a great virtue, while Chutzpah is generally a negative trait.

An extreme form of Chutzpah is exemplified by someone who murders his parents and then claims that the court should be lenient with him because he is an orphan. A more common form is seen by a child who speaks rudely to a parent, or by a student speaks to a teacher without respect. Chutzpah usually means that someone is doing or saying something that is not appropriate.

Rebbe Yehudah ben Teima made two statements in Pirkei Avos (5:23,24), to be bold as a leopard... to fulfill the will of Hashem; and, the brazen go to Gehinom, but the bashful ones goes to the Gan Eden. In the first statement, we see that being bold, in Hebrew, Az, is a virtue. In the second statement, he uses the strongest language to condemn someone who is brazen, in Hebrew, Az Panim. What makes the difference between the quality that is very positive and the one that is very negative?

Rav Zelig shares a story: When I was a young child, I was fearless around other people. I had the ability to say whatever came to my mind. At first, I was too young to understand that I needed to be more diplomatic about what I said and how I said it. My parents kept telling me to refrain from saying things that they told me were Chutzpadik to say. But I would argue, “Why is this chutzpah? This is the truth.” As a child, I didn’t realize that even when speaking the truth, there are unacceptable ways to express oneself. I didn’t realize that even when speaking the truth, there are acceptable ways to express oneself, and there are unacceptable ways.

Teachers kept telling me that I have Chutzpah, and I would disagree with them. I didn’t understand why they didn’t understand that I was speaking the truth. Finally, I had a teacher who understood me. This teacher realized that I didn’t mean to do anything wrong. My teacher told me, “You have a tremendous talent, but you have a responsibility to use it for the good. You need to be more aware of how the way you say things affects people. You will be able to do many acts of kindness with your ability to say whatever you feel is right. You will be able to ask people to donate money to Tzedakah and worthwhile organizations. You will be able to suggest to people that they need to correct their actions and their Middos. But what you have is like dynamite. It can be used for building, and it can also be used for destroying. The more powerful the explosive, the more careful one needs to be with it.”

This teacher gave me several private lessons to help me differentiate between positive and negative ways to say things. This was the most important lesson in the world for me. I am very grateful that this teacher didn’t just tell me that I had Chutzpah. Rather, this teacher showed me how to utilize it properly!”

Reprinted from the Parshas Terumah 5786 email of Rabbi Yehuda Winzelberg’s Torah U’Tefillah.

Rav Zelig Pliskin

Rav Zelig Pliskin writes that boldness and brazenness are two sides of the same coin. One leads to great acts of courage, and the other can cause great harm, but both can be turned to do good. Chutzpah and courage have certain elements in common. But they are on the opposite ends of the scale. Courage is a great virtue, while Chutzpah is generally a negative trait.

An extreme form of Chutzpah is exemplified by someone who murders his parents and then claims that the court should be lenient with him because he is an orphan. A more common form is seen by a child who speaks rudely to a parent, or by a student speaks to a teacher without respect. Chutzpah usually means that someone is doing or saying something that is not appropriate.

Rebbe Yehudah ben Teima made two statements in Pirkei Avos (5:23,24), to be bold as a leopard... to fulfill the will of Hashem; and, the brazen go to Gehinom, but the bashful ones goes to the Gan Eden. In the first statement, we see that being bold, in Hebrew, Az, is a virtue. In the second statement, he uses the strongest language to condemn someone who is brazen, in Hebrew, Az Panim. What makes the difference between the quality that is very positive and the one that is very negative?

Rav Zelig shares a story: When I was a young child, I was fearless around other people. I had the ability to say whatever came to my mind. At first, I was too young to understand that I needed to be more diplomatic about what I said and how I said it. My parents kept telling me to refrain from saying things that they told me were Chutzpadik to say. But I would argue, “Why is this chutzpah? This is the truth.” As a child, I didn’t realize that even when speaking the truth, there are unacceptable ways to express oneself. I didn’t realize that even when speaking the truth, there are acceptable ways to express oneself, and there are unacceptable ways.

Teachers kept telling me that I have Chutzpah, and I would disagree with them. I didn’t understand why they didn’t understand that I was speaking the truth. Finally, I had a teacher who understood me. This teacher realized that I didn’t mean to do anything wrong. My teacher told me, “You have a tremendous talent, but you have a responsibility to use it for the good. You need to be more aware of how the way you say things affects people. You will be able to do many acts of kindness with your ability to say whatever you feel is right. You will be able to ask people to donate money to Tzedakah and worthwhile organizations. You will be able to suggest to people that they need to correct their actions and their Middos. But what you have is like dynamite. It can be used for building, and it can also be used for destroying. The more powerful the explosive, the more careful one needs to be with it.”

This teacher gave me several private lessons to help me differentiate between positive and negative ways to say things. This was the most important lesson in the world for me. I am very grateful that this teacher didn’t just tell me that I had Chutzpah. Rather, this teacher showed me how to utilize it properly!”

Reprinted from the Parshas Terumah 5786 email of Rabbi Yehuda Winzelberg’s Torah U’Tefillah.

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