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The account of Gideon’s son Avimelech (Abimelech) in this chapter is a good illustration of what the oft-misinterpreted Torah phrase, "eye for eye, tooth for tooth," really means. What Avimelech sowed in grasping for power came down on him like a millstone.
Food for thought
Notice the parallel between the nickname of Gideon, Yerub-Ba’al (Hebrew for "contends with the lord"), and Ya’akov’s, Yisra’el (Hebrew for "struggles with God"). How is Avimelech (Abimelech) a judge of Israel in one sense and in another sense an oppressor? How appointed the other judges, and how appointed Avimelech?
How did Gideon’s ephod (Judges 8:22-35) turn his descendants into pagan dictators?
How did the Ephraimite desire for power in Yisrael at the time lead to the rise of Avimelech? How did his pitch for rulership (Judges 9:2) have the grain of truth commonly used by good liars in swaying people?
What was the symbolic meaning of giving 70 pieces of silver from the pagan temple of Ba’al-B’rit (Hebrew for "lord of a covenant") to kill the son of Yerub-Ba’al (Judges 9:3-6)? What do the sages say about Avimelech’s actions in going to "his father’s home"?
What is the "pillar of Shechem" (Judges 9:6)? What two mountains was Shechem located between? Why did Yotam (Jotham) pronounce curses from Mt. Gerazim (Judges 9:7) and not from Mt. Ebal? How was the passing of a curse from the mountain of blessing (Mt. Gerazim) show that the Shechemite attempt to pronounce blessings by anointing Avimelech for an evil task would turn into a curse upon them? How was that twist pointed out in Yotam’s parable of the olive tree, fig tree, vine and thornbush (Judges 9:7-15)?
What group of people even today still worship on Mt. Gerazim (John 4:20)?
What is the significance of the olive tree in the parable? Who was to harvest the olive oil for use in the tabernacle menorah (Hebrew for "lampstand")? Why would the symbolic olive tree not give olives for oil (Deut. 28:40)? Which of the noble first judges did the sages call the "olive tree of Israel," and why (Judges 3:9-14)?
What is significant about the fig tree in the parable? What does such a tree produce before putting out leaves? How does a fig tree look before putting out figs and leaves? How is a fig tree symbolic of the relationship between a person and the Torah? Who was "the fig tree" among the major first judges? What did that judge produce that was good before becoming a judge (Judges 4:5)?
What’s the point of the vine in the parable? Why are all three plants in Judges 9 mentioned in Deuteronomy 28? What is symbolized by the juice of the grape? What did Gideon provide Israel — from a winepress, even — when it was being oppressed by Midian (Judges 6:11)?
How does wine "cheer God and men" (Judges 9:13)? What is God creating in us by tending our "vines" and our "fruit" (John 15:5)?
What is the significance of the thornbush in the parable and throughout Scripture? Do thornbushes produce much shade? How fast do dry thornbushes burn? What is the point of the sarcasm Yotam passed along related to the people of Shechem (Judges 9:16-20)?
How was Avimelech able to find mercenaries in Shechem? How was that city set aside for a purpose in the original division of the land of Israel among the tribes (Joshua 21:21)?
Where did Ga’al ben-Eved (Gaal son of Ebed) come from in this account (Judges 9:28)? How did his arrival on the scene make the people feel confident against the random attacks of Avimelech’s men? Why really ruled Shechem, Zebul or Ga’al?
Why doesn’t Avimelech stop fighting when Ga’al is driven out of Shechem? Who set up the ambush for Avimelech, Ga’al or Shechem? How was the town of Thebes involved with Shechem, largely based on proximity? What lesson did Avimelech miss in being hit mortally by a woman’s millstone (Judges 9:50-57)?