After their 40 year sojourn in the desert, the Jews coming into the Land of Israel were required to fulfill 3 commandments sequentially, each one contingent on the performance of the previous one: 1) anoint a king, 2) annihilate Amalek, and 3) build the Holy Temple. (Sanhedrin 20b)

Amalek is the most severe kelipa and therefore must be absolutely vanquished in the time of the redemption….

The Torah states, "Amalek is the 'rosh' of the nations." (Num. 24:20) Rashi explains "rosh" to mean the "first", as Amalek was the first nation to do battle with the Jews after they went out of Egypt. But Kabbalah explains "rosh" literally, as "head"; Amalek is the "head" of the evil nations in the world and supplanted the Primordial Snake, which first brought death and impurity into the world (Sharei Ora). It is this negative force which implants doubt and indecision in the minds of those who would serve G‑d faithfully and without question. In fact, the Baal Shem Tov points out the numerical value of "Amalek" is "safek", Hebrew for "doubt".

It is the most severe kelipa and therefore must be absolutely vanquished in the time of the Redemption. As the Jewish king is ideally the embodiment of selflessness and accepting upon oneself the yoke of Heaven, he is the one uniquely able to vanquish Amalek, and indeed his own kingship is incomplete until then. (Adir Bamarom II 7, kings; see Jewish Royalty)

Quality of leadership

A true leader acknowledges his mistake readily, as did Judah, who immediately accepted responsibility for Tamar's pregnancy, not paying attention to the shame he brought on himself, thereby saving her from death. As a result, Jacob proclaimed that the tribes themselves would admit that the kingship belongs to Judah, both in this world as well as in the next. (Rabbeniu Bachya Gen. 49:9) David, Judah's descendent, acted in a similar manner upon being admonished by the prophet Natan after causing Uriah's death and taking Batsheva as his wife prematurely. A righteous leader also tries to put it right if at all possible.

The fact that he was anointed king he didn't tell….

Saul was "young and handsome, there being no one of the children of Israel handsomer than he; from his shoulders and upwards he was taller than any of the people." (Samuel I 9:2) Yet he had outstanding modesty and humility and an innate nobility of character. When Samuel came to anoint him King of Israel, he responded, "Am I not a Benjamite, of the smallest of the tribes of Israel and my family the least of all the families of Benjamin?" (Samuel I 9:21) Then, when he returned home from his encounter with Samuel, Saul told his uncle what had happened to him concerning the lost mules and the asses that he had gone to seek, but the fact that he was anointed king he didn't tell.

Kabbalah teaches that Saul's soul was rooted in what is known as the "World of Concealment" (Nekudat Tzion, yesod of Imma, the "World of the Male"), while that of David is from the "Revealed World" (yesod of Nukva, or Nekudat Tzion ViYerushalayim). For this reason, Saul was modest - i.e. hidden.

Being from the world of Tohu, His kingship, could not endure….

Saul's soul root lay in the sixth of the Kings of Edom, relating to the sefira of yesod, whose name was the same as his; this king was one of the Edomite Kings whose death is mentioned explicitly (see Gen. 36:37). Thus Saul "reigned… and died". Being from the world of Tohu ("chaos"), His kingship, could not endure. David, on the other hand, is rooted in the world of Tikun ("repair"), and for this reason his kingship endured. (Likutei Torah in the Writings of the Ari, on Samuel I 17)

Although the house of royalty was destined to be from Judah, who had the trait known as "hoda'a" - both gratefulness and acknowledgement, Saul, although from the tribe of Benjamin, deserved to be king in his own right, but wasn't destined to father a succession of royalty.

Saul's failings

There are different sources enumerating Saul's errors and the reasons for his downfall.

His great humility was misplaced at times and caused him to falter in leadership. When Saul waged battle with the Philistines and Samuel commanded him to wait for him before offering the sacrifices they had prepared, Saul acquiesced to the impatience of his soldiers. He was then told that his kingdom would not last.

He was rebuked for being "small in your own eyes" and not assertive enough in his mission as "the head of the tribes of Israel".

King Saul also thought himself more righteous and compassionate than G‑d himself and didn't complete the full extermination of the nation of Amalek. This was his first historical mission as king of Israel and was meant to usher in the time of the Mashiach. Instead he spared Agag their king and "the best of the sheep and the cattle, and the fatlings, and on the fattened sheep, and on all that was good; and they did not want to destroy them". Not only that, but the next morning when Samuel came to rebuke him (after killing Agag himself), initially Saul tried to explain away his actions. Had he initially recognized his mistake and repaired the damage himself, he conceivably could have regained favor in G‑d's eyes, for a penitent is even more favorable than a completely righteous person. After being rebuked, Saul did indeed express remorse, but it was too late.

The reaction was quick and harsh. G‑d regretted having made him king and declared that his reign wouldn't last long. There are those that maintain that Saul reigned for only 2 years. Also, Samuel ceased to come to him, instead seeking out David, his successor. Regarding this error, the Talmud states, "Be not overly righteous like Saul, who thought to be more righteous [than G‑d Himself] and had mercy on the wicked [Amalek]." (Yoma 22b)

Both compassion as well as cruelty need be utilized for the service of G‑d….

All character traits have been created for a purpose and each has its proper function in the world. Both compassion as well as cruelty need be utilized for the service of G‑d. It was grave disobedience for Saul to have thought his compassion superior to that of G‑d Himself. Yet the decree against Saul wasn't finalized until his error involving the sin of accepting slander regarding the priests (kohanim) of the city of Nob, in which he mistakenly ordered the slaughter of all the priests in the city, of which only one survived.

The Baal Shem Tov teaches us that when one comes before the Heavenly Tribunal upon his death, he is shown someone else who seemingly has sinned and is asked to voice his opinion on the case (just as the prophet Natan asked David to pass judgment on "the poor man's lamb" - see Sam II 12). Only after he passes judgment is it demonstrated to him that his deeds were similar, and thus he decides his own verdict in the Afterlife.

Until this episode, Saul could have maintained that he acted against Amalek according to his overly merciful nature - an error, to be sure. But once he showed his own cruel side regarding the city of Nob, he is judged to have been rebellious against G‑d on both occasions.

Anyone who sins and is ashamed, not making excuses for himself, all his sins are forgiven, as the verse states: "'…that you remember and be ashamed, and you will no longer have an excuse by reason of your humiliation, when I forgive you for all that you have done,' says the L-rd G‑d." (Ezekiel 16:63; Berachot 12b) Therefore, David the paramount repentant, merited to have a royal line of kings descend from him, whereas Saul's reign lasted a mere 2 years, notwithstanding his outstanding character traits.

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