Joy Brings Success Sadness Leads to Failure
למודי משה | February 28, 2026
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Joy Brings Success Sadness Leads to Failure

למודי משה | February 28, 2026

Joy Brings Success, Sadness Leads to Failure

ותתחלחל המלכה מאד ותשלח בגדים להלביש את מרדכי ולהסיר מעליו שקו
“The queen [Esther] was greatly distressed; she sent garments to clothe Mordechai, and to remove the sackcloth from upon him.” (Esther 4:4)

The Tiferes Shlomah asks: “Why did Esther send clothing to Mordechai? Did she think Mordechai didn’t have clothes to wear?”

The Tiferes Shlomah answers: Mordechai and Esther debated how to annul Haman's decree. Mordechai followed the path of crying and mourning to arouse Hashem’s pity and sympathy. Esther believed they would accomplish more with joy, so she sent Mordechai proper clothing.

The Tiferes Shlomah writes: “When Esther heard Mordechai's loud cries for Klal Yisroel, she sent him clothing and asked him to remove his sackcloth. She was implying that he shouldn’t be in agony. Instead, he should gird himself with joy and daven to Hashem with joy. Mordechai disagreed because one needs to begin with humility and fear and only afterwards with joy.”

They both agreed that joy was necessary. Their debate was only about how to begin. Esther believed they could start with joy, and Mordechai understood they must begin with remorse. However, they both understood that joy was necessary for the salvation to come.

The Megillah elaborates on the honor Mordechai received from Haman as Haman led him through the streets of Shushan. Why was this episode so important?

The Tiferes Shlomah zt”l explains: “Mordechai was asked to ride the king's horse, dressed in the king's clothes. People sang and played music before him. All this was to make Mordechai happy. Immediately after Mordechai was happy, Klal Yisroel's salvation arrived, and the wonderful miracle occurred.”

All honor accorded to Mordechai was just for Mordechai to be happy, and when there was happiness, the salvation arrived.

The Gemara (Megillah 16a) says: “Haman took the king's clothing and horse and went to Mordechai. Mordechai began to daven, and Haman waited until Mordechai finished davening.” Then Haman led Mordechai through the streets of Shushan with immense honor.

The Ben Yehoyada ask: Why did Haman wait until Mordechai finished davening? Why didn’t he tell him right away that he came to honor him?

He answers: “Haman knew that Mordechai was davening with sadness, and Haman preferred it that way. Haman thought, 'If I interrupt his tefillah, he will need to daven again. And after hearing the good news [that I must honor him], he will daven with immense joy, and then it is likely that his tefillos will be answered.’”

Haman preferred that Mordechai daven with sadness because the tefillos are less effective, so he waited patiently until Mordechai finished davening.

At the first party, Achashveirosh said: מה שאלתך וינתן לך ומה בקשתך עד חצי המלכות ותעש – “What is your request? It will be granted to you. What is your petition? [Even if it be] until half the kingdom, it shall be fulfilled” (5:6). What better time to express her plea for Bnei Yisroel, but Esther's only request was that Achashveirosh and Haman come to the second feast, which she would host the following day. Why did she push off pleading for the Jewish nation? This seemed like such an ideal time! Achashveirosh told her that almost whatever she asked for, he would give her!

The answer is that Haman was happy at the first party, as it states:ויצא המן ביום ההוא שמח וטוב לב – “That day Haman went out joyous and exuberant" (5:9). Esther knew she couldn’t bring down Haman when Haman was happy, so she pushed off pleading for the Jewish nation for the next day.

The next day Haman was sad, as it states (Esther 6:12): אבל וחפוי ראש – “despondent, and with his head covered." That was an ideal time to bring about Haman's downfall. Indeed, Haman was hanged that day. This teaches us that joy brings success (and even for a rasha like Haman), and sadness leads to failure. (R’ Elimelech Biderman)

Joy Brings Success, Sadness Leads to Failure

ותתחלחל המלכה מאד ותשלח בגדים להלביש את מרדכי ולהסיר מעליו שקו
“The queen [Esther] was greatly distressed; she sent garments to clothe Mordechai, and to remove the sackcloth from upon him.” (Esther 4:4)

The Tiferes Shlomah asks: “Why did Esther send clothing to Mordechai? Did she think Mordechai didn’t have clothes to wear?”

The Tiferes Shlomah answers: Mordechai and Esther debated how to annul Haman's decree. Mordechai followed the path of crying and mourning to arouse Hashem’s pity and sympathy. Esther believed they would accomplish more with joy, so she sent Mordechai proper clothing.

The Tiferes Shlomah writes: “When Esther heard Mordechai's loud cries for Klal Yisroel, she sent him clothing and asked him to remove his sackcloth. She was implying that he shouldn’t be in agony. Instead, he should gird himself with joy and daven to Hashem with joy. Mordechai disagreed because one needs to begin with humility and fear and only afterwards with joy.”

They both agreed that joy was necessary. Their debate was only about how to begin. Esther believed they could start with joy, and Mordechai understood they must begin with remorse. However, they both understood that joy was necessary for the salvation to come.

The Megillah elaborates on the honor Mordechai received from Haman as Haman led him through the streets of Shushan. Why was this episode so important?

The Tiferes Shlomah zt”l explains: “Mordechai was asked to ride the king's horse, dressed in the king's clothes. People sang and played music before him. All this was to make Mordechai happy. Immediately after Mordechai was happy, Klal Yisroel's salvation arrived, and the wonderful miracle occurred.”

All honor accorded to Mordechai was just for Mordechai to be happy, and when there was happiness, the salvation arrived.

The Gemara (Megillah 16a) says: “Haman took the king's clothing and horse and went to Mordechai. Mordechai began to daven, and Haman waited until Mordechai finished davening.” Then Haman led Mordechai through the streets of Shushan with immense honor.

The Ben Yehoyada ask: Why did Haman wait until Mordechai finished davening? Why didn’t he tell him right away that he came to honor him?

He answers: “Haman knew that Mordechai was davening with sadness, and Haman preferred it that way. Haman thought, 'If I interrupt his tefillah, he will need to daven again. And after hearing the good news [that I must honor him], he will daven with immense joy, and then it is likely that his tefillos will be answered.’”

Haman preferred that Mordechai daven with sadness because the tefillos are less effective, so he waited patiently until Mordechai finished davening.

At the first party, Achashveirosh said: מה שאלתך וינתן לך ומה בקשתך עד חצי המלכות ותעש – “What is your request? It will be granted to you. What is your petition? [Even if it be] until half the kingdom, it shall be fulfilled” (5:6). What better time to express her plea for Bnei Yisroel, but Esther's only request was that Achashveirosh and Haman come to the second feast, which she would host the following day. Why did she push off pleading for the Jewish nation? This seemed like such an ideal time! Achashveirosh told her that almost whatever she asked for, he would give her!

The answer is that Haman was happy at the first party, as it states:ויצא המן ביום ההוא שמח וטוב לב – “That day Haman went out joyous and exuberant" (5:9). Esther knew she couldn’t bring down Haman when Haman was happy, so she pushed off pleading for the Jewish nation for the next day.

The next day Haman was sad, as it states (Esther 6:12): אבל וחפוי ראש – “despondent, and with his head covered." That was an ideal time to bring about Haman's downfall. Indeed, Haman was hanged that day. This teaches us that joy brings success (and even for a rasha like Haman), and sadness leads to failure. (R’ Elimelech Biderman)

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