The Fathers of Israel were all circumcised as were the Jews who left Israel. Moses, Aaron and Joshua were all circumcised and were there the entire 40 years. If they understood the value and importance of circumcision why were none of the Jewish men who were born in the desert cicrumsised?
Joshua 5:2 - 8
NLT - 2 At that time the Lord told Joshua, “Make flint knives and circumcise this second generation of Israelites. ” 3 So Joshua made flint knives and circumcised the entire male population of Israel at Gibeath-haaraloth.
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I can't cite a specific supporting passage from Scripture, but, in my opinion, the omission of circumcision during Israel's wanderings in the wilderness was a judgment or punishment from God (along with His command to the Israelites in Numbers 14 to turn back and not enter the Promised Land). This, to me, is the only explanation with sufficient authority to explain why Moses would have allowed circumcisions not to be performed. This would have represented a rejection on God's part of that entire adult generation, who (in God's view) were not worthy to perform or see the sign of the covenant relationship with Him represented by the circumcision of their male descendants (Genesis 17:9-14) because of their rebellion against Him by seeking to return to Egypt, rather than dealing with the obstacles found by the spies who had been sent to report back to the Israelites on the Promised Land and its inhabitants (Numbers 13). This rejection remained in place until the last member of that adult generation had died, prior to entry into the Promised Land. The punishment aspect of this is confirmed for me by God's command to Joshua cited in the question to resume circumcision, which is mentioned by God as rolling away the reproach that was represented by the omission of circumcision in the prior forty years (Joshua 5:9).
There were apparently many portions of the law which were not supposed to be observed until the people entered the Promised Land. Deuteronomy 12 starts a discussion of these portions of the law and it continues for several chapters. 8 You are not to do as we do here today, everyone doing as they see fit, 9 since you have not yet reached the resting place and the inheritance the Lord your God is giving you. 10 But you will cross the Jordan and settle in the land the Lord your God is giving you as an inheritance, and he will give you rest from all your enemies around you so that you will live in safety. 11 Then to the place the Lord your God will choose as a dwelling for his Name—there you are to bring everything I command you: your burnt offerings and sacrifices, your tithes and special gifts, and all the choice possessions you have vowed to the Lord. 12 And there rejoice before the Lord your God—you, your sons and daughters, your male and female servants, and the Levites from your towns who have no allotment or inheritance of their own. 13 Be careful not to sacrifice your burnt offerings anywhere you please. 14 Offer them only at the place the Lord will choose in one of your tribes, and there observe everything I command you. Some of these things would be difficult to observe where there is not a permanent home and the entire camp was expected to be ready to move with only a few hours notice (or less when the cloud rose up from the tabernacle.) With other things, such as the Sabbath years it was more a symbolic matter, but with a practical aspect. During the 40 years God had not brought them to a place of rest so there was no way to observe a rest year. The land itself was a Sabbath (Isa 28:12) and until you are there you cannot really rest. For whatever reason there was a certain level of leniency in some matters until the people entered into the land and apparently circumcision was one of these matters. That is not to say that none of these people observed this rite, but rather as verse 8 says, "Everyone doing as they see fit." Some saw the need to circumcise their sons and others did not. But no one who was not circumcised could enter into the land under God's protection, so Joshua had make certain everyone was circumcised before the first battle began, or actually, even earlier, before the Passover could be observed in the land. Only then could they be assured of God's protection as they moved forward to conquer the land.
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