Summary: After the Jewish people demand Samuel appoints a king, Saul is chosen as the first Jewish king by God. He meets Samuel after looking for some lost donkeys. Following his anointment, he gathers the people. Yet some are sceptical about their new king and ridiculed Saul, although he remained silent.
A deeper look: When Jacob blessed his sons shortly before his death, he indicated that the Jewish monarchy would rest with Yehudah (Judah) and remain within their tribe (Genesis 49:10). Yet before Saul is anointed as king, his lineage reveals from the outset that he is from the tribe of Benjamin (Samuel I 9:1). While Rashi explains that the Torah means that from the appointment of David as king, royalty will remain with Yehudah, it begs the question why a Benjaminite king should have been appointed in the first place.
While the Jewish people had many enemies, perhaps the greatest threat came from the tribe of Amalek. Originally, it was Amalek who had attacked the fledgling Israelite nation on their way out of Egypt (Exodus 17:8). Indeed, they paved the way for other nations to attack at a time when the Jewish people should have been at their strongest (Midrash Tanchuma on Ki Teitzei 13).
Another Midrash relates a conversation between Mordechai and Haman regarding Mordechai’s refusal to bow down to Haman. Haman asked Mordechai why he refused to bow down to him, given that his ancestors had all bowed down to Haman’s ancestor Esau (Genesis 33:6-7). Mordechai replied that his ancestor Benjamin had not bowed down as he had not yet been born (Esther Rabbah 7:8).
While the fact that Jacob’s family had originally bowed to Esau was understandable as an act of showing honour, rather than worship, it weakened the ability of their descendents to overcome the force of Amalek. This explains why Saul was initially chosen to lead the Jewish people; as a Benjaminite he had that special merit. This is also why Mordechai and Esther were able to defeat Haman who was a descendant of Amalek (Esther 3:1) as they were direct descendants of Saul (Esther 2:5,7). Yet for all Saul’s potential, his mission will ultimately turn sour.