We remember that the Amalekites harassed Israel during the Exodus, attacking the rear of the column where the infants, elderly and sick were riding in wagons. It was universally regarded as a cowardly act, the kind of thing for which the Amalekites were well known. It’s hard to pin down just who these people were, and the name cannot be restricted clearly to descendants of a man by that name. Rather, it appears he gave his name to some people his descendants joined. Balaam refers to them as a very ancient nation that may have been around before Abraham (Numbers 24:20), but that they would be wiped from history.
By the time of Saul’s reign, the Amalekite range was centered on the Wilderness of Zin, an area west of Edom, and starting just south of the usable land held by Judah. As near as we can estimate, Telaim is the name for an area near Ziph, down in the Negev, not far from the western border of Edom. At that time the border of Edom would be some poorly defined area they guarded in or near the southern rift valley rising out of the Dead Sea. Saul was marshaling his troops on the eastern end of the Amalekites’ range.
Their “city” was probably little more than a dense collection of tents with some stacked stone and piled sand fortifications. They were distinctly nomadic. The attack would hardly wipe out their whole nation, since they ranged all over the Sinai Peninsula. However, it would reduce their numbers significantly, since this was likely the single biggest concentration of them.
The Kenites that Saul advised to leave the area were a tribe noted for their metallurgical skills. The most memorable member of that tribe was Jethro, Moses’ father-in-law. They had done Israel no harm, so Saul was being fair with them.
The attack ranged on the eastern end from some place call “Havilah.” It turns out this may have been a generic descriptive name instead of any actual place, because the label shows up in the Bible all over the Ancient Near East (ANE), starting with a reference point for the river flowing through Eden. It appears to mean any really sandy area, which could be anywhere in the eastern Negev. The slaughter continued westward to the ancient highway known as the Way of Shur that ran from Egypt, through the central highlands in Palestine, and all the way to Assyria.
Saul’s carnal nature showed through in the victory march home. He saved their King Agag and all the better livestock found in Amalekite possession. The purpose in holding the king would be to keep him as a living trophy in Saul’s court, a common practice among ANE warlords. The troops took the livestock as plunder, though a lion’s share would have belonged to Saul. Notice that everything followed rather uncivilized tribal customs common to nomadic tribes in that part of the world.
The Lord warned Samuel that Saul could not be trusted to obey Him. For this, Samuel wept all night, because he was very fond of Saul. In the morning, Samuel learned that Saul had returned to a town named Carmel (not the mountain up north on the coast) near where he had marshaled his army and set up a monument to himself. From there, he came around the western edge of the highlands to Bethel, and then down to Gilgal in the Jordan Valley. This remained somewhat a national headquarters still.
The exchange when they met later that day showed Saul was unrepentant. He talked as if he had no real control over his army, and that they seized the livestock as plunder. Then Saul tried to make it sound like they were planning on using the livestock as offerings. Here we have the famous verse that God puts a very high value on obedience over ritual observance. God cannot be bribed, but He can be won by a faithful heart. This is the soul of the Covenant itself, to live as faithful and loving children adopted by the Father.
Saul’s confession of his failure rings hollow. He was more worried about his reputation, having Samuel’s presence with him in front of the troops, than he was about God’s will. He begged Saul to stay for the ritual victory celebration, essentially a thanksgiving service of worship. There was a dramatic moment when Saul grabbed the edge of Samuel’s cloak and tore it by accident, and Samuel remarking how it symbolized God tearing the reign from Saul. Again, Saul very painfully cared only for his reputation. So Samuel relented, but it was a bitter celebration for him.
By this time Agag is pretty sure he’s safe, so when Samuel demands to see him, the Amalekite comes out rather cheerfully to meet the nation’s chief shaman. Samuel was completely unsparing, pronouncing sentence and executing him on the spot by his own aging hands. It was a ritual slaughter symbolizing God’s wrath on the nation of Amalek.
Samuel returned to his home in Ramah, and Saul headed back to Gibeah. The two never met formally again. The Lord is characterized as regretting making Saul king.