Good morning!
Greetings in the name of Father, Son and Holy Spirit.
And Gideon said to him, “Please, sir, if the LORD is with us, why then has all this happened to us? And where are all his wonderful deeds that our fathers recounted to us, saying, ‘Did not the LORD bring us up from Egypt?’ But now the LORD has forsaken us and given us into the hand of Midian.” (Judges 6:13)
The Israelites were oppressed by the Midianites. It was not a random event. The Israelites did what was evil in the sight of the Lord, and God gave them in to the hand of Midian for seven years. During the period, the Midianites overpowered the Israelites, and took sheep, ox, donkey, and devour the produce of the land. They came like locusts in number, and they lay waste the land as they came in. Israel was brought very low.
Gideon was one of the Israelites, who was not much different from others. He was equally in fear of the Midianites. From the fear, Gideon was beating out wheat in the winepress to hide it from the sight of the Midianites. Then suddenly an angel of Lord appeared to him, and said to him “The Lord is with you, O mighty man of valor.” (Judges 6:12) It was totally unexpected. For the last seven years, the Israelites including Gideon had never experienced God’s presence.
Gideon was not able to keep silent, and expressed his frustration, which was always lingering in his heart: “Sir, if the LORD is with us, why has all this happened to us? “ For the last seven years, Gideon did not experience God, and he doubted God from the deepest part of his heart. If the God existed, all these bad things that he saw and experienced for the last seven years should have had not happened, especially to the Israelites, the God’s chosen people.

Bible records the reason: the people of Israel did what was evil in the sight of the LORD. (Judges 6:1a) They abandoned the LORD, the God of their fathers, and went after other gods while bowing down, which God hated most. (By the way, we might easily say we have never bowed down and worshiped an idol, because we have never done it before. In fact, it is not so clear cut. We, human beings, always worship and serve something, whether it is wealth, fame, prestige, and even physical strength, health, self and ego. Often we don’t notice while we worship these gods. But we will know what we really worship when we lose what we truly worship – we become really frustrated, and even angry and mad at God. Then it was our idol and we used to worship. This is the most terrible sin before God because we worship our own idol other than God, whom we should worship under all circumstances.)
The Israelites were worshipping their own idols, and complained to God. (They should have had eliminated their idols and worshiped God.) Thus, God, who dearly loved the Israelites, was in great pain, and He had to give out the Israelites to other people so that they suffered from their unfaithfulness and rebellious acts against God. God patiently waited till they came back to Him and cried for help. Yes, the Israelites suffered, but the pain of God was even greater than that the Israelites experienced.
After seven years, the Israelites’ suffering was sufficient. They were ready. God sent an angel to Gideon. The gracious God, first, let Gideon open his heart and vent out his frustration and resentment. Gideon poured out his pain and anguish question from the deepest part of his heart, and Gideon was heard by God. (Imagine God personally listens to your frustration and pain out of the deepest part of your heart. In reality, God always does for all His children.) Gideon vented his heavy burden in his heart, and his heart became much lighter. Then God gave Gideon a new mission of rescuing Israel by saying: “Go in the strength you have, and rescue Israel from the Midianites. Am I not sending you?” (Judges 6:14)
Gideon quickly looked at the reality — his feeble hand, himself and his heart full of fear. In fact, he was so afraid of the Midianites that he was hiding in the winepress, while beating out wheat. He knew he was nothing but one coward person. Thus, he humbly opened his mouth and said: “Please, Lord, how can I save Israel? Behold, my clan is the weakest in Manasseh, and I am the least in my father’s house.” (Judges 6:15) His clan was the weakest in the Manasseh tribe, and he was also the least in his father’s house. Before the angle, he authentically confessed that he was not up to the task of saving Israel.
God, who saw Gideon’s authenticity and humility from his heart, said to him, “I will be with you, you will strike down all the Midianites, leaving none alive.” (Judges 6:16) When Gideon initially met the angel of God, and was told: “The Lord is with you. O mighty man of valor.” Gideon missed the most important part of the conversation – The Lord is with you. Although Gideon was a mere ordinary person being scared by everything around him including the Midianites, God was about to transform him as a mighty man of valor. Indeed, Gideon initially could not hear. The fear of the Midianites prevented him from hearing what was told by God. Thus, God patiently led Gideon step by step. At the end, God transformed him as the man of valor that God truly wanted. Here was what God did:
First God let Gideon fully unload all fears completely occupying his heart. Second, God let Gideon directly see who he was, and let him authentically cry out his weakness and inability to God with humility and meekness. Then Gideon was able to truly hear what God said: “I am with you.” What an assuring word from God. Initially, Gideon could not hear this assuring words from God, but God patiently and lovingly approached him through the angel until he was able to hear the most loving word from God – “I am with you.”
Why did God so tenaciously approach Gideon? God loved Gideon and His people who were suffering, and God chose Gideon to save from the Midianites, who painfully oppressed the Israelites for the seven years. The Midianites took literally everything from the Israelites. To avoid the oppression, the Israelites had to hide themselves. Gideon was not different. He was threshing wheat at the bottom of a winepress to hide the grain from the Midianites.

The LORD is near to all who call on him,
to all who call on him in truth.
He fulfills the desire of those who fear him;
he also hears their cry and saves them. (Psalm 145:18-19)