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Num 13:1 Yahweh spoke to Moses, saying,

Num 13:2 Send men, that they may spy out the land of Canaan, which I give to the children of Israel. Of every tribe of their fathers, you shall send a man, every one a prince among them.
Num 13:3 Moses sent them from the wilderness of Paran according to the commandment of Yahweh: all of them men who were heads of the children of Israel.
Num 13:4 These were their names. Of the tribe of Reuben, Shammua the son of Zaccur.
Num 13:5 Of the tribe of Simeon, Shaphat the son of Hori.
Num 13:6 Of the tribe of Judah, Caleb the son of Jephunneh.
Num 13:7 Of the tribe of Issachar, Igal the son of Joseph.
Num 13:8 Of the tribe of Ephraim, Hoshea the son of Nun.
Num 13:9 Of the tribe of Benjamin, Palti the son of Raphu.
Num 13:10 Of the tribe of Zebulun, Gaddiel the son of Sodi.
Num 13:11 Of the tribe of Joseph, of the tribe of Manasseh, Gaddi the son of Susi.
Num 13:12 Of the tribe of Dan, Ammiel the son of Gemalli.
Num 13:13 Of the tribe of Asher, Sethur the son of Michael.
Num 13:14 Of the tribe of Naphtali, Nahbi the son of Vophsi.
Num 13:15 Of the tribe of Gad, Geuel the son of Machi.
Num 13:16 These are the names of the men whom Moses sent to spy out the land. Moses called Hoshea the son of Nun ‘Joshua’.
Num 13:17 Moses sent them to spy out the land of Canaan, and said to them, Go up this way by the South, and go up into the hill country;
Num 13:18 and see the land, what it is, and the people who dwell therein, whether they are strong or weak, whether they are few or many;-
 
v.
18-20 These requests seem to be Moses' weakness or at least, concession to Israel's weakness. God told them to simply search the land, presumably in order to be able to divide it up for conquest and inheritance. Moses instead asks the spies to assess whether the land is good or not, how strong the opposition will be, etc. And this weakness was the undoing of Israel. Indeed Dt. 1:22 says that Israel asked God to send out the spies before them- even though God had promised that the Angel in the pillar of cloud would go ahead of them. God grants such concessions to human weakness, but making use of them often leads us into greater openness to temptation and likelihood of failure.
Time and again in the Biblical record, Abraham is held up as a very real example, in whose steps all God's people are to tread. For example, as Abraham was bidden leave Ur and go and "see" the "land" of promise which God would "give" him (Gen. 13:15), so the spies were told to go and "see" the "land" which God had "given" them (Num. 13:18; 32:8,9- the same three words as in the promises to Abraham)- yet they lacked the faith of Abraham to believe that really, they could possess that land. They did "see" the land, yet they were punished by being told that they would not now "see the land" (Num. 14:23; Dt. 1:35). They saw it, but they didn't "see" it with the eyes of Abraham. And so it can be with our vision of God's Kingdom. Remember that Moses was the author of both Genesis and Numbers- such connections aren't incidental. Moses wished the people to see themselves as going forward in the spirit of Abraham- and hence he wrote up the Genesis record for Israel's benefit an inspiration.


Num 13:19 and what the land is that they dwell in, whether it is good or bad; and what cities they are that they dwell in, whether in camps, or in fenced cities;
Num 13:20 and what the land is, whether it is fat or lean, whether there is wood therein, or not. Be courageous, and bring of the fruit of the land. Now the time was the time of the first-ripe grapes.
Num 13:21 So they went up, and spied out the land from the wilderness of Zin to Rehob, to the entrance of Hamath.
Num 13:22 They went up by the South, and came to Hebron; and Ahiman, Sheshai, and Talmai, the children of Anak, were there. (Now Hebron was built seven years before Zoan in Egypt)-

Although not recorded in Num. 14:24; Dt. 1:36, it appears Caleb was specifically promised Hebron at that time. Caleb had explored that area as a spy (Num. 13:22) and taken a special liking to it. We see therefore his spiritual ambition; 'this shall one day be mine'. And we can do the same, as we in this life spy out our future inheritance.  


Num 13:23 They came to the valley of Eshcol, and cut down from there a branch with one cluster of grapes, and they carried it on a staff between two. They also brought some of the pomegranates and figs.
Num 13:24 That place was called the valley of Eshcol because of the cluster which the children of Israel cut down from there.

Num 13:25 They returned from spying out the land at the end of forty days.
Num 13:26 They went and came to Moses and to Aaron, and to all the congregation of the children of Israel, to the wilderness of Paran, to Kadesh, and brought back word to them, and to all the congregation, and showed them the fruit of the land.
Num 13:27 They told him, and said, We came to the land where you sent us and surely it flows with milk and honey and this is its fruit.
Num 13:28 However the people who dwell in the land are strong, and the cities are fortified and very large. Moreover, we saw the children of Anak there-
Rahab informed the later spies that the cities were fortified from fear of Israel, and the Canaanites were weak and fearful before Israel at this time (Josh. 2:10,11). Those obstacles to our inheritance of the Kingdom which seem to us huge and too strong for us may actually be very weak and far easier to overcome than we imagine.


Num 13:29 Amalek dwells in the land of the South; and the Hittite, and the Jebusite, and the Amorite, dwell in the hill country; and the Canaanite dwells by the sea, and along by the side of the Jordan.
Num 13:30 Caleb stilled the people before Moses, and said, Let us go up at once, and possess it; for we are well able to overcome it-
The Bible often records the immediacy of response in faithful people. Procrastination and endlessly weighing up the difficulties often leads to failure to act as we should.


Num 13:31 But the men who went up with him said, We aren’t able to go up against the people; for they are stronger than we-
 
Caleb and Joshua perceived that Israel were “well able” to overcome the tribes and inherit the land, seeing that the Angel-hornet had gone ahead and prepared the way; and yet due to Israel’s disabling of this possibility at the time, it was in some ways so that God Himself was “not able” to give them the inheritance, because they judged that they were “not able” to take it (Num. 13:30,31; 14:16).


Num 13:32 They brought up an evil report of the land which they had spied out to the children of Israel, saying, The land, through which we have gone to spy it out, is a land that eats up its inhabitants; and all the people who we saw in it are men of great stature-
This was effectively calling God’s descriptions of the promised land untrue. If we don’t believe we can inherit the Kingdom prepared for us (Mt. 25:34), then we are effectively calling God a liar. Ps. 106:24 says that they didn’t believe God’s word of promise that they would possess the land (Gen. 15:18; 17:8; Ex. 23:30). These promises were clear and unambiguous; but the immediate and the visible seemed more true to them than the promises of God’s word. Perhaps they had forgotten those promises, not recited them to themselves, not bothered to attend Moses’ sessions of instruction, of which the Pentateuch is likely a transcript. Unless God’s words of promise are regularly in our consciousness, we will likewise fail to believe it when we come up against the human obstacles in our paths.


Num 13:33 There we saw the Nephilim, the sons of Anak, who come of the Nephilim, and we were in our own sight as grasshoppers, and so we were in their sight-
 
They made the common mistake of assuming that our view of ourselves is how others also see us. The Israelites were seen as grasshoppers by their enemies- and so this is how they came to perceive themselves (Num. 13:33). Prov. 23:7 RV observes: “As he reckoneth within himself, so is he”. We are defined by our own self-perception. We must come in the end to perceive ourselves from God’s perspective and not according to how men perceive us. We must see ourselves from outside ourselves, and thereby “guide thine own heart in the way” (Prov. 23:19).

The people were frightened by the "giants" they met in the land of Canaan (Num. 13:33), likely connecting them with superhuman beings. These nephilim [LXX gigantes] had their origin explained by Moses in Genesis 6 (see on Gen. 6:4)- the righteous seed intermarried with the wicked, and their offspring were these nephilim, mighty men of the world. Note in passing how Ez. 32:27 LXX uses this same word gigantes to describe pagan warriors who died- no hint that they were superhuman or Angels.  According to Jewish traditions (as reflected in 1 Enoch and the Book of Jubilees), the supposedly sinful Angels ("the Watchers") morally corrupted human beings in the lead up to the flood by teaching them to do evil, astrology, weapon making and the use of cosmetics (1 Enoch 7-8, 69; 10; 21.7-10; 64-65; 69; Jub. 5:16-11; 8:3). Yet the Genesis record simply states that the descendants of Cain started to do all those things, their wickedness increased, and so they were punished through the flood (Gen. 4:20-22). Constantly in the Jewish Apocryphal writings there is a shifting of blame from humanity to Angelic beings.