Regretful royal recalcitration
נחמתי כי-המלכתי את-שאול למלך כי-שב מאחרי ואת-דברי לא הקים וגו’ ויבא שמואל אל שאול ויאמר לו שאול ברוך אתה ליקוק הקמותי את דבר יקוק: ויאמר שמואל ומה קול הצאן הזה באזני וגו’
“I have regretted coronating Shaul to be King, for he has turned away from Me and he did not uphold My words”…Shmuel came to Shaul, and Shaul said to him: “Blessed are you to Hashem! I have upheld the word of Hashem.” Shmuel said: “Then what is this sound of sheep I hear in my ears?”
King Shaul was tasked with the command to eradicate the memory of the wicked nation of Amalek. The entire nation, as well as their animals, were to be destroyed. Shaul was mostly successful, except that he left the King Agag alive, as well as the Amalekite sheep. When the prophet Shmuel came to rebuke Shaul for his failure, Shaul said: “I have upheld the word of Hashem!” This is astounding, for he surely must have realized that he didn’t. He didn’t follow the command as he was told. What was he thinking? Also, he uses an unusual expression. Shouldn’t he have said “I have fulfilled the word of Hashem”? Shmuel responded that he heard the sound of sheep. Why did he choose to rebuke Shaul this way?
The Torah tells us that someone who doesn’t uphold the words of the Torah is cursed. Our Sages teach that someone who learned Torah, and fulfilled Torah, but didn’t make it everlasting, is included in this curse. What does this mean? The Ramban explains that someone who could have created fences around the Torah, to ensure it’s continued fulfillment, and didn’t, is the subject of this curse. An outgrowth of this is the concept that our Sages will sometimes uproot something from the Torah in a passive way, if the end result is the fulfillment of the Torah in some other way.
We find an example of this in the Megillah. After the Jews successfully defeated their enemies, who were primarily from the nation of Amalek, the Megillah testifies that the Jews didn’t touch the spoils of the battle. Why not? Rashi explains there was a concern that Achashverosh, who gave them permission to defend themselves in battle, would accuse them of going to battle solely for the spoils. Now, this sounds pretty reasonable. What was the problem? Well, why did they simply leave the spoils where they were, where anyone could just take them? Why didn’t they bring them to King Achashverosh’s treasury? Haman offered to pay the royal treasury for the rights to kill the Jews, so why didn’t the Jews offer the same to Achashverosh?
However, according to what we said, it makes perfect sense. The mitzvah to eradicate Amalek is so all encompassing, that there’s a mitzvah to destroy even their sticks and stones. There should be no remnant of them or their name, whatsoever. If so, the Jews should have burned all of the spoils of war to a crisp. Why didn’t they? Because they were concerned what Achashverosh would think. He would look at it as an excessive act of cruelty to not only kill the Amalekites, but to burn all of their possessions. What gave Mordechai permission to ignore an explicit Torah command? He had the power to uproot something from the Torah in a passive way. The purpose? To avoid the ire of Achashverosh, and the potential inability to keep the Torah which could follow. However, Mordechai didn’t have ability to have the Jews bring the spoils to the King’s treasury, as that would have been an active uprooting of the Torah.
We can now understand the exchange between King Shaul and Shmuel. Hashem told Shmuel that He regretted making Shaul king, “for he turned away from Me and did not uphold My words”. Meaning, Shaul broke the Torah, but not in a legally authorized way, as we shall see. He could have done so to ensure the Torah is fulfilled, but only when it is uprooted properly. This is alluded to in the phraseology of “did not uphold My words”, an allusion to the curse to one who does not uphold the Torah.
However, Shaul was afraid of the people, and thought that he could ensure a fulfillment of the Torah through his deviation of Hashem’s command. He reasoned that if he didn’t listen to the people, who were telling him to spare the animals of Amalek, then they wouldn’t listen to him at all to wage war with Amalek in the first place. That’s why he told Shmuel that “I have upheld the word of Hashem”. Meaning, I ensured the Torah was fulfilled, that Amalek would be eradicated, by uprooting something from the Torah, namely by ignoring the command to wipe out the animals.
What was Shmuel’s response? “What’s this sound of sheep that I hear?” Meaning, no question if Shaul had passively uprooted the Torah, it would have been justified. However, why did Shaul bring the spoils of war, namely the flock of Amalek, to his camp? This was considered an active uprooting of the Torah, for which there is never justification.
 Based on Derashos Chasam Sofer I p. 188 col. 4 s.v. בהפטרה
 I Samuel 15:11,13,14
 Deuteronomy 27:26
 Vayikra Rabbah 25:1
 Ad. loc.
 Yevamos 90a
 This is the Chasam Sofer’s addition to the gemarra. I’m not sure his source, or if it always holds true, or is a general rule. See also Maharatz Chayes’ Toras Neviim Chapter 3 Hora’as Sha’ah s.v. ואולם, who seems to use this concept as well. See as well the Chasam Sofer’s review of this work in Teshuvos Chasam Sofer Orach Chaim § 208
 Esther 9:10
 Ad. loc.
 Orchos Chaim Hilchos Megillah § 41, in the name of an unknown Midrash, brought by the Beis Yosef to Tur Orach Chaim 690:17. This Midrash is also brought by the Abudraham Tefillas Purim s.v. וכתב אבן הירחי and Biur HaGra ad. loc.
 The Chasam Sofer’s exact words are לא עבר על דברי להיות עי”ז קיום התורה, which I don’t really understand, as his intent was indeed that the Torah be fulfilled…