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Gideon, along with Samson and Deborah, rounds out the "Big Three" of the judges. He grows to become one of Israel's greatest deliverers, despite his persistent spiritual reluctance. Visited by an angel as a young man, he nevertheless doubts both himself and the Lord's power. He wonders, "If the Lord is with us, why then has all this happened to us? […] The Lord has cast us off" (6:13). And later, he asks, "How can I deliver Israel? My clan is the weakest in Manasseh, and I am the least in my family" (6:15). Despite his doubts, he eventually becomes a decisive and godly leader, but only after repeated miracles to convince him that God's got his back.
From inauspicious beginnings vandalizing the altars of Baal worshipers (6:25-27), the Lord inspires Gideon to rally an army to rise against Israel's Midianite oppressors, with some help from his trumpet (more on that later—Gideon loves the brass section). Yet each step of the way, Gideon says, in essence, "Now God, don't be mad, but could you show me just one more sign that this is going to turn out okay?" (see 6:13, 17-18, 36-40; 7:9-11) Several wet fleeces (6:36-40) and giant dinner-roll dreams (7:9-15) later, Gideon's moment to (literally) shine comes when he invents the legendary lamp-in-the-water-pitcher trick, with a trumpet maneuver thrown in (see 7:16-22).
Forever thereafter, he seems to have gained confidence in himself and in God. When the people ask him to be king, he piously declines, saying, "I will not rule over you, and my son will not rule over you; the Lord will rule over you" (8:23). He judges Israel during a time of prosperity, which would be wonderful were it not for the fact that we know that Israel gets spoiled really easily.
Gideon's story ends somewhat tragically, since after his death Abimelech, one of his sons, goes fratricidal in a huge way, decimating Gideon's numerous posterity (a.k.a. almost his entire family) and ending the peace that he ushered in (see 9:1-6).