In this chapter, Gideon is chosen to save Israel from Midian.
Gideon is probably the second-best known of the judges of Israel, behind Samson, and his story is both richly detailed and interesting (to me, at least). The overall pattern of this story is the same as for every other judge, with Israel once again doing "evil in the sight of the LORD", given over to their enemies, and now Gideon is being raised up to save Israel from their troubles.
This time around, their national enemy is the Midianites (allied with the Amalekites and "the sons of the east"). We have seen the Midianites a few times before, but until now they have been politically neutral more than anything else. For instance, Joseph was sold by his brothers to Midianite traders (Gen 37:28). Later, Moses flees to Midian and marries a daughter of "the priest of Midian" (Ex 3:1). One of the sons of Abraham is also named Midian (Gen 25:2), but given the timelines involved I think it's unlikely that the Midianite traders were descendants of Abraham's son Midian. Since Joseph is a great-grandson of Abraham, that would leave around three generations for Midian to grow from a single person to a widespread national identity. It is more likely to be a coincidence. Another possibility is that Abraham (who himself came from the east) named his son Midian after the Midianites.
Nevertheless, from what descriptions of the Midianites we have seen before and in this chapter, it seems likely that the Midianites are an eastern people and mostly nomadic. As described in v. 5, they possessed vast herds of livestock, and from Gen 37:28 we know that they would range up and down from the Levant to Egypt. Their alliance with "the sons of the east" further suggests that the Midianites lived in parts of the desert, possibly in the Arabian peninsula or maybe Iraq, although in the bible Iraq is usually called Shinar or Babylon. There aren't any direct references that I know of to the home of the Midianites, and indeed their nomadic culture would imply that their home, if anywhere, is a widespread region that possibly overlaps with other national territories.
With that background in mind, this chapter marks two divergences from what we have previously known. The first is that (as I said) Midian was not hostile to Israel before, and indeed Midian does not appear to share any common borders with Israel. Midian's invasion of Israel suggests a regional power shift, because they would have had to either invade or pacify at least one of the nations around Israel to get through (i.e. Moab, Ammon, or some of the Amorite kingdoms to the northeast). The second divergence is that the Midianites, as a nomadic tribe, did not previously seem to have such large numbers. Although horses and camels act as substantial force multipliers in battle, it is historically very uncommon for nomadic peoples to be so successful against agrarian societies (which can usually sustain much higher populations). The Mongols were able to conquer almost the entire world in the 14th century under Genghis Khan, and the Arabs were able to conquer almost the entire world in the centuries following the life of Muhammad, but these are exceptional cases. Most other empires in world history, and certainly in biblical history, were agrarian. The big empires in biblical history are: the Egyptians, the Assyrians, the Babylonians, the Persians, the Greeks and the Romans. I might be forgetting one or two, but all six of these empires I listed were agrarian societies.
I guess what I'm trying to say is that the Midianites, as a nomadic people, are not who you would expect to become such a threatening regional force. And yet here we are, with the Midianites devouring all the crops of Israel "like locusts". The Israelites get so used to oppression that they start making caves and mountainous fortresses to save their lives while the lowlands and valleys get overrun.
At this point, the LORD rebukes them through a prophet. And yet, he chooses to save them again. Rebuke, yet save. And there is little evidence to suggest that Israel will stop sinning once they are saved from the Midianites, yet still he saves. It's hard to explain why the LORD would save. But if the LORD chooses to forgive, who am I to question him?
With all that in mind, we find Gideon "beating out wheat in the wine press". A wine press would be like a pit or something, where they would dump grapes and them trample on them to squeeze out the juice (which would then be collected and fermented). Grains of wheat taken from a stalk is not particularly edible because it is covered by a hardened shell called a "hull". The hull protects the wheat from pests, but also protects it from human consumers. To render it edible, the wheat is "beaten" to break off the hull into fragments called "chaff". Then the wheat would be thrown into the air using a shovel or something, so that the air can carry off the lighter, fragile chaff, while the heavier wheat kernel (which is the edible part) falls back down and can be gathered together. This process is usually called "threshing" the grain.
Gideon's behavior, threshing the wheat inside a pit, is therefore unusual. Normally threshing is done on hilltops where the stronger and more consistent wind patterns will separate the chaff more easily. Threshing inside a wine press will not separate the chaff as effectively, and if the chaff is ground together with the kernels then the resulting wheat flour is of lower quality. Why is Gideon doing this? Because as v. 11 tells us, he is trying to "save it from the Midianites". By threshing it inside a wine press, it would be harder for the Midianites to see him and to steal his crops. This is the kind of behavior you expect from a thoroughly cowed individual. We can see, then, that Gideon is not acting much like a hero. The Israelites are living in caves in the mountains out of their fear and desperation, while Gideon is threshing grain in a wine press out of his own fear. The LORD appears to him in v. 12 and calls him a valiant warrior.
This is a central paradox to both the OT and the NT, because it is fundamental to how the LORD relates to people. One example of this is Deut 7:7, where it says that the LORD did not choose Israel because they were strong or numerous, because Israel was "the fewest of all peoples". Indeed, it was because of their weakness that the LORD chose them, to reveal his power the most clearly through them. Even before that, the LORD chose people (through Adam and Eve) to administrate the planet and the animals therein, even though they were made out of dust. Some people might say it was "in spite of" their weakness that the LORD chose them, but from the bible it seems more likely that it was "because of" their weakness, working his power through us to reveal himself to us and to everyone around.
By the same token, the LORD demonstrated miracles and signs when he brought Israel out of Egypt, both to reveal himself to Israel but also to reveal himself to Egypt and all the nations in that part of the world. And now he chooses to do the same thing with Gideon, but in an even more exaggerated way, taking the youngest son from the smallest family in Manasseh, out from threshing in his wine press, to be the next judge of Israel. This is the first wonder of this chapter.
The second wonder of this chapter begins in verses 17-18, when Gideon asks for the LORD to show him a sign, and the LORD agrees. Gideon prepares an offering to the LORD and when the LORD sets it on fire and disappears, Gideon fears for his life (just as Jacob did in Gen 32), but the LORD reassures him. After this first sign, the LORD asks him to destroy an altar of Baal and replace it with an altar to the LORD. This is less than what the LORD first told him, that he would destroy the Midianites. But what we should see from this is how the LORD is building up Gideon's confidence. After having stated his destiny (to overthrow the Midianites) and then showing him a miracle (setting the offering on fire with his staff) he now asks him to perform a lesser task, destroying an altar. His success at this lesser task will also give him confidence for the greater task.
Even then, Gideon is still afraid, so he destroys the altar at night. He gets discovered (probably because he brought 10 servants with him), but his father convinces the other Israelites of his own town (who had been worshiping Baal) to not kill him.
After this, Gideon asks the LORD for a second miracle, to reassure him for the greater task of overthrowing Midian. He asks for a wet fleece and dry ground, then dry ground and a wet fleece. The LORD fulfills both requests, at which point Gideon has enough confidence to attack Midian with the army he has gathered (in the next chapter).
I think this whole series of miracles is very interesting. I'm not exactly sure how to put it, but there are many people in the world who are trying to figure out "God's will for their life", trying to understand what God wants them to do or what they should be doing. Many of these people are also afraid that they will miss what God wants them to do. The story of Gideon has led my friends to sometimes use an expression, "put out a fleece". Used in a sentence: "If you think God wants you to quit your job, put out a fleece and see what happens". What we mean by this expression is to establish some sort of concrete litmus test that would guide whether you are hearing from the LORD correctly or not.
Generally speaking, we only "put out a fleece" when contemplating a radical departure from the normal or what we would otherwise do and feel unsure if it's the right thing to do. To put it in simpler terms, if you think the LORD is asking for radical faith, it's reasonable to ask for a fleece. Gideon's fleece is not a radical miracle like Moses's staff turning into a snake, but it was concrete and physical, something that Gideon knew could not naturally happen and it was sufficient proof for him that the LORD was truly speaking to him and he could risk his life. In the case of Moses, he had to convince all the elders of Israel that the LORD was with him, so a greater miracle was required. In the case of Gideon, he only needed to convince himself. It's not like bigger miracles are better; each miracle is appropriate for the situation in which it is given.
So getting back to "God's will for your life", my general philosophy is that we have to try to listen to what the LORD is saying, and when you think he says "do this" and it is risky or unusual and you aren't sure if it's the LORD, then seek confirmation. Put out a fleece, and if it's the LORD and you are asking genuinely, then he will do it. The actual nature of the "fleece" is variable, and can be nearly anything in practice, like "let there be a rainbow in the sky today" or whatever. It doesn't actually matter what it is, as long as it's something unlikely or unnatural enough to be convincing. If you have no doubt, then it's disingenuous to put out a fleece, but if you have doubt, then putting out a fleece is fair and from what I understand, the LORD will honor it.