ויהי דבר-יקוק אל-שמואל לאמר: נחמתי כי-המלכתי את-שאול למלך כי-שב מאחרי ואת-דברי לא הקים וגו’ ויאמר שמואל הלוא אם-קטן אתה בעיניך ראש שבטי ישראל אתה וימשחך יקוק למלך על-ישראל וגו’
And it was that the word of Hashem came to Shmuel, saying: “I have regretted coronating Shaul to be King, as he has turned away from Me and has not fulfilled My words.”…Shmuel [later said to Shaul]: “Is it not true that you view yourself as insignificant? You are the head of the tribes of Israel! Hashem has anointed you to be King over Israel…”
This week is the week before Purim. As such, for maftir we read parshas Zachor, which enumerates the mitzvos involved in remembering what the nation of Amalek did to us when we left Egypt. As well, we read a special haftarah, recounting the sin of King Shaul. He was commanded by the prophet Shmuel to put an end to the evils of the nation of Amalek, and he failed to do so. The gemarra makes an interesting observation: King Shaul transgressed one mitzvah and had to suffer the consequences. He was punished with an early death, and the kingship was taken away from his descendants and given over to David. This is unlike King David, who transgressed two mitzvos and kept the kingship. Why was this so?
After Shmuel informed King Shaul he had sinned, he told him the root cause of his downfall: King Shaul was “small in his eyes”. He viewed himself as unimportant. This is what caused him to stumble. King Shaul admitted this was true, when he responded: “It was because I feared the nation [of Israel]”. He wanted their support, and gave in to their demands. What was the problem? Even though the trait of humility is extremely lofty and ideal, this is only in the proper circumstances. Shaul, as the King of Israel, shouldn’t have made use of his trait of humility. He was instead supposed to take on the persona of royalty. The nation should be in awe of him, not that he be afraid of his nation.
This is why King Shaul was punished for this one sin, while King David wasn’t for his two. The sins of King David were the transgressions of mitzvos, for which he repented and was forgiven. He therefore didn’t lose the kingship. With King Shaul on the other hand, the root cause of his sin was his middos. Even though he repented for the transgression itself, he lost the kingship. This is because the underlying motivator for the sin, his misplaced humility, wasn’t corrected. This trait was a contradiction to his being King, so he lost the kingship to David.
In truth, every character trait is neither inherently good or bad. Each one has their time and place. When used correctly, they’re good. When misused, they’re bad. For example, most of the time, jealousy can be destructive. However, Chazal teach us that קנאת סופרים תרבה חכמה, the jealousy of one’s peer’s scholarly achievements can be an inspiration to become wiser. This is considered properly using the trait of jealousy, and is thus viewed as positive.
We see an example of choosing middos appropriate to the circumstances with Avraham. When he had to expel his son Yishmael from his home, he only gave him some bread and a pitcher of water. Rashi explains that Avraham hated Yishmael for having become wicked. However, later by the Akeidah (the binding of Yitzchak), Hashem commanded Avraham to offer his beloved son as an offering. Avraham asked which son, for he had two which he loved. We see that Avraham’s feelings for his sons Yitzchak and Yishmael were equal. Doesn’t this contradict what happened earlier, that Avraham hated Yishmael for the way he had turned out?
The explanation is based on the above principle. Usually, hatred is caused by a blemish a person has in their middos. If this were the case with Avraham, then it would indeed be a contradiction. When there is love, there is no room for hatred, and when there is hatred there is no room for love. However, the hatred Avraham displayed at that time didn’t come from his middos. Therefore, even though Yishmael was as dear to Avraham as his beloved son Yitzchak, he was able to display this hatred. Since Yishmael had gone so bad, Avraham chose to act towards Yishmael with hatred. He felt that was the appropriate trait to use at that time. Therefore, he only gave him menial provisions for the wilderness, despite his intense love.
This was King Shaul’s mistake. He misplaced and misused his middos. He was extremely humble, but this was not a proper way for a King to behave. Another incident shows this as well. Chazal say another reason he was punished was because he waived his due-honor. The verse says that at the beginning of King Shaul’s inauguration there were lawless men who were insulting Shaul, and he simply ignored them. Normally, it is a praiseworthy attribute to waive the honor that you may deserve. However, in this instance it was inappropriate. A King isn’t supposed to forgo his honor. What this is really saying is his improper use of his middos is what led to his downfall. Since he didn’t act the way a king is supposed to, the kingship was taken away from him.
 Based on Sichos Mussar § 53
 I Samuel 15:10, 11, 17
 Deuteronomy 25:17-19, as ruled by Shulchan Aruch Orach Chaim 685:2, 5. Mishnah Berurah § 1 explains it’s to juxtapose the parsha to the downfall of Haman (a descendant of Amalek). This is to precede the destruction of Amalek with the memory of what they did to us in the wilderness
 I Samuel 15:2-34
 Yoma 22b
 Rashi ad. loc. explains that his sin with Amalek caused this. However, Tosafos Yeshanim ad. loc. point out that really King Shaul earlier had transgressed a command not to bring an offering until Shmuel had arrived. It was then that these punishments were determined (see I Samuel 13:14)
 The incident with Uri HaChiti, Bas-Sheva’s husband (see II Samuel 11:15) and conducting an inappropriate census (see II Samuel 24:1)
 I Samuel 15:24
 It’s one of the final traits to acquire in Mesillas Yesharim, which is ordered from easiest to hardest
 Kesubos 17a
 See Avos 4:21
 Bava Basra 21a
 Genesis 21:14
 Ad. loc.
 Rav Chaim Shmuelevitz brings Midrash Tanchuma Vayeira § 22 that Hashem responded the one who you love dearly, to which Avraham said he felt the same about them both
 Rav Chaim Shmuelevitz rejects the possibility that Yishmael had done teshuva at this point (now thirty years later), as Chazal (Bava Basra 16b) only infer he did teshuva when Avraham died, and not earlier. Although, my chavrusa R’ Shlomo Laufer asked a good question: why would Avraham bring Yishmael with him to the Akeidah (see Genesis 22:3 with Rashi, whose source is Vayikra Rabbah 26:7) if he was still wicked?
 See Likkutei HaGra to Proverbs 1:3 who also says this idea
 Yoma loc. cit.
 I Samuel 10:27
 Rosh Hashanah 17a
 Rav Chaim Shmuelevitz continues his piece and develops the idea that a lack of a calm mind can lead to impulsive sins, which is something we see from King Shaul; see there