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Deut. 6:20-23 says,
20 When your son asks you in time to come, saying, "What do the testimonies and the statutes and the judgments mean which the Lord commanded you?" 21 Then you shall say to your son, "We were slaves to Pharaoh in Egypt; and the Lord brought us from Egypt with a mighty hand. 22 Moreover, the Lord showed great and distressing signs and wonders before our eyes against Egypt, Pharaoh and all his household; 23 and He brought us out from there in order to bring us in, to give us the land which He had sworn to our fathers."
Before answering the question of meaning, we are first reminded of God's right to give the law and to expect obedience. God's right is established by the law of redemption. God redeemed Israel from Egyptian bondage, and so Israel changed masters according to the law of Lev. 25:53. In other words, Israel was a purchased slave, even as Christians have been purchased by the blood of Jesus Christ and are expected to be obedient to their new Master (Rom. 6:18).
Verse 23 says, "He brought us out. . . in order to bring us in." Bringing them out of Egypt was not the goal. Neither is our goal justification by faith, which brought us out of that greater house of bondage. Justification is a means to an end, the beginning of our journey. But before God can "bring us in" to the promised inheritance, He must first teach us obedience. Without the obedience which is learned through the feast of Pentecost, we will not have sufficient faith to enter the Promised Land at the feast of Tabernacles.
Further, there would be little point in granting immortality to men through the feast of Tabernacles, if the law were not written on their hearts. Why should God create a class of immortal sinners? If that had been the plan, He would never have sent Adam and Eve out of the garden. But we see that He separated Adam and Eve from the Tree of Life and posted cherubim to guard it with a flaming sword (Gen. 3:24).
That flaming sword is the "fiery law" (Deut. 33:2). The law does not allow sinners to enter the Paradise of immortality. To regain this inheritance, one must qualify in the sight of the law. We qualify only because Jesus Christ paid the full penalty of the law for our sin. But when we are thus justified by faith, God Himself requires obedience and not mere justifying faith before He will "bring us in."
Those who remain lawless in this life time will not inherit the First Resurrection of Rev. 20:4-6. Jesus made this clear in Matt. 7:23, saying, "depart from Me, you who practice lawlessness." They will be turned away in the same manner that the Israelites were turned away at the border when they proved to have insufficient faith (Num. 14:30). They will have to await the second opportunity at the general resurrection (Rev. 20:11-3) a thousand years later.
That thousand years parallels Israel's 38-1/2 years of extra wilderness time, as they learned obedience. Life spans will increase during that thousand years (Is. 65:20), but nonetheless, they will die as mortals, so that they may be raised from the dead at the general resurrection along with the rest of mankind. Jesus spoke of this in John 5:28, 29.
Hence, only a relatively small number of people will qualify for the First Resurrection. These are like Caleb and Joshua who represented the overcomers in their day. Of course, Caleb and Joshua were men like us also. I do not believe they were perfect in the absolute sense, for they too were mortal, and, as Paul says in Rom. 5:12, we sin because we are mortal. Because of one man's sin, "death spread to all men, on which all sin."
So an overcomer is not one who is perfected, but one who is allowing Pentecost to have its effect in one's life--that is, being obedient to the Spirit's leading and allowing the Spirit to write the law in one's heart.
One way or another, God will bring the Church into the Promised Land, for that was His purpose in bringing us out of the house of bondage at Passover. Israel's disobedience set a pattern of delay in that "church in the wilderness" (Acts 7:38), and this same delay has occurred for the same reason in the New Testament Church. Scripture teaches us two things very clearly: (1) God will bring the Church into the Promise by faith, but (2) God will not allow the Church to inherit the Promise without first learning obedience.
The purpose of Pentecost is to teach obedience, even as the purpose of Passover was to create the Church itself by faith in the blood of the Lamb. Pentecost is thus mandatory, for it stands in the middle between Passover and Tabernacles.
Moses continues in Deut. 6:24 and 25,
24 So the Lord commanded us to observe all these statutes, to fear the Lord our God for our good always and for our survival [chayah, "to live"], as it is today. 25 And it will be righteousness for us if we are careful to observe all this commandment before the Lord our God, just as He commanded us.
The Apostle Paul, an avid student of the law, confirms Moses in Rom. 7:12, saying,
12 So then, the Law is holy, and the commandment is holy and righteous and good.
Yes, the law was meant "for our good always." Likewise, it was "for our survival" (NASB). Better, it was to establish life, or the path of living a long life that has quality, health, and peace in the land. However, because the old carnal man is lawless, Paul says, the law turned out to be the means of his death as a judgment for sin. So he says in Rom. 7:10,
10 and this commandment, which was to result in life, proved to result in death for me; 11 for sin, taking opportunity through the commandment, deceived me, and through it killed me.
So Paul affirms Moses' words that the purpose of the law was to bring life. But in reality, because of a prior problem that was rooted in Adam's sin, that same righteous law could not acquit the guilty. For this reason, the law could only condemn the old man to death. Hence, there is only one way to obtain life, and that is through Christ, who paid the full penalty required by the law. Faith in Him is the only source of life, or immortality.
Paul does not cast out Moses, as many of the Jewish believers claimed (Acts 21:21). Paul affirmed Moses' words, but applied them by the New Covenant. The conflict between Paul and the Judaizers was over the changes that necessarily had to be made under the New Covenant. Those changes are fully detailed in the book of Hebrews.
The law, being the expression of the holiness of God, could justify only those who were perfect by its righteous standard. But because "all have sinned" (Rom. 3:23), the law could justify no man (Rom. 3:20) who was born of the first Adam. The Old Covenant demanded man's obedience in order to receive the promise. The New Covenant demanded faith in Jesus Christ, who alone could fulfill the righteous standard of the law and also pay the penalty for the sin of the world, in order that the law might be satisfied and justify the faithful.
Hence, the problem was not the law. The holiness of God is not the problem. The problem was that the Old Covenant was insufficient to save, because no sinner could qualify by his own merit to receive the promise of immortality. The New Covenant provided a better way, a way of faith that relied upon the righteousness of Jesus Christ alone. Under the Old Covenant, man's righteousness is in accordance with his own ability to keep the law. Under the New Covenant, Christ's righteous life is imputed to us.