Sisera was the commander of the Canaanite army who cruelly oppressed the Israelites for twenty years trying to recover the territory once ruled by the kings of Hazor (Judges 4:3). Ultimately, he was killed by Jael, the wife of a Kenite he considered to be an ally, when she drove a tent peg through his skull while he slept. The record of his defeat is found in Judges chapters 4 and 5.
Deborah, a prophetess judging Israel at the time, encouraged Barak to obey God's call to lead an army to Mount Tabor where God would deliver Sisera into Israelite hands (Judges 4:6–7). Barak agreed only on the condition that Deborah accompany them. Deborah assented, but prophesied, "Nevertheless, the road on which you are going will not lead to your glory, for the LORD will sell Sisera into the hand of a woman" (Judges 4:9). It is important to note that while Jabin was the Canaanite king "who reigned in Hazor," it was Sisera, the commander of the army who posed the most threat to Israel.
Sisera, who lived in Harosheth-hagoyim at the time, most likely due to Hazor still lying in ruins after Joshua's victory there (Joshua 11:10), gathered 900 iron chariots and all the men from Harosheth-hagoyim (Judges 4:13). In this way, he would have had both a technological as well as a manpower advantage over the Israelites' 10,000 men gathered at Mount Tabor (Judges 4:10). However, "the LORD routed Sisera and all his chariots and all his army before Barak by the edge of the sword. And Sisera got down from his chariot and fled away on foot. And Barak pursued the chariots and the army to Harosheth-hagoyim, and all the army of Sisera fell by the edge of the sword; not a man was left" (Judges 4:15–16).
Sisera fled to the nearby tent of Heber the Kenite. The Kenites had once been allies of Israel, but Heber had chosen to move north and ally himself with the Canaanites. His wife, Jael, invited Sisera into her tent and made him feel safe, offering him shelter, milk, and a mat for sleeping. While he slept, she drove a tent peg through his temple and killed him. When Barak came in pursuit of Sisera, Jael showed him her accomplishment. "So on that day God subdued Jabin the king of Canaan before the people of Israel. And the hand of the people of Israel pressed harder and harder against Jabin the king of Canaan, until they destroyed Jabin king of Canaan" (Judges 4:23–24). "And the land had rest for forty years" (Judges 5:31).
Thus God saved Israel, the land flowing with milk and honey (Exodus 3:8), by using Jael, whose name means "mountain goat" (that produces milk) and Deborah, whose name means "bee" (that produces honey). These two women are credited with Sisera's defeat and are mentioned in Deborah's song celebrating these events in Judges chapter 5.
Sisera's cruel oppression of Israel is recalled by Samuel in 1 Samuel 12:9 and his resounding downfall is recalled by the psalmist in Psalm 83:9. So Sisera stands as an example of an enemy against God's people, whom God defeated so "that they may know that you alone, whose name is the LORD, are the Most High over all the earth" (Psalm 83:18).
As a brief note, there is one other person named Sisera in the Bible: a temple servant, listed in the list of names of exiles who returned in Ezra 2:53 and Nehemiah 7:55. Nothing else is known about him.
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