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When Israel first received the law at Sinai, the stated reason for its observance was to commemorate God's Rest after completing His work of creating all things.
From there, Israel went to Kadesh-barnea just south of Canaan and prepared to enter the land. They sent 12 spies, but ten of them gave an evil report, which the people believed. So God told them they would spend 40 years in the wilderness until that generation was dead.
Hebrews 4 tells us that the people could not enter God's Rest because of unbelief--that is, lack of faith. The people did have sufficient faith to leave Egypt at Passover, so it can be said that they had faith on Level One. But by the time they arrived at Sinai for Pentecost, they ought to have had faith on Level Two, going (as Paul says) "from faith to faith" (Rom. 1:17).
They refused to hear the Word for themselves at that first Pentecost (Ex. 20:18-21), because they were incapable of having Pentecostal faith. Having stagnated there, they certainly would not be able to increase to Level Three faith and enter the Promised Land at Tabernacles. If they had progressed properly, the 12 spies would have given good reports, the people would have believed them, and they would have blown the trumpet on the 50th Jubilee from Adam. Then they would have entered the Promised Land five days later on the Feast of Tabernacles.
In other words, the Kingdom of God would have been established (if such were possible) under Moses. The people would have become the manifested sons of God, fulfilling the feast of Tabernacles. But it is self-evident that God wanted us to be born and include us in the big plan. So the plan was extended in time.
Israel had a Passover Kingdom; the Church has had a Pentecostal Kingdom (under "Saul"); and we now are part of the work in establishing the Tabernacles Kingdom (under "David").
Each Kingdom has its unique Sabbath focus. Israel's Sabbath hinged upon Passover (i.e., the Second Passover). When Moses gave the Second Law (Deuteronomy), the Sabbath commemorated Israel's deliverance from Egypt, rather than God's Rest as such (Deut. 5:15). Israel was delivered at Passover. So it is no surprise that God would bring Israel into Canaan at the time of Passover, rather than at Tabernacles.
It was a Passover Kingdom, having as Passover Sabbath, that reflected a Passover-level of Faith. Yet they were not allowed to enter God's Rest (Heb. 4:3). Verse 9 says,
"There remains therefore a Sabbath rest for the people of God."
The point is that Israel had a Sabbath, but it was not the one originally intended, nor was it the highest "rest" that God had for us. Their Sabbath reflected their Passover level of faith and not God's Rest, which is the Jubilee.
There are three levels of Sabbath, even as there were three Sabbaths in Scripture. There was the Sabbath DAY, the Sabbath YEAR, and the Jubilee. These parallel Passover, Pentecost, and Jubilee/Tabernacles. Only the third one is truly God's Rest, as the book of Hebrews describes.
Israel's Sabbath years were based upon the year that they entered Canaan, rather than the 50th Jubilee from Adam. There was a 38-year discrepancy between these years. Neither their rest years nor their Jubilees aligned with the Creation Rest. After the Babylonian captivity, when Daniel's 70 weeks jump-started their calendar once again (in 458 B.C.), their rest-years aligned, but their Jubilees remained seven years off from God's Rest.
Daniel's 70th week represented the seven-year discrepancy, as I have shown elsewhere.
The most important point of law that we ought to understand is found in the change of timing between Passover and the wave-sheaf offering. This is built into the law itself. It is not a man-made change. Passover was on a fixed day of the month. They were to kill the lambs on the Preparation Day, Abib 14, and then remain vigilant all night. The day of Passover was Abib 15, which began at Sundown after the Preparation Day.
Jesus' death on the cross shows us what Passover was about. It prophesied of His death, even as the lambs were to be killed. But this death was followed by His resurrection and presentation as the Son of God in the Temple in heaven. This presentation was marked by the waving of the sheaf of barley in the temple on earth at the third hour of the day on the Sunday following Passover.
For prophetic purposes, it does not really make a difference when Jesus actually rose from the dead. The wave-sheaf offering marked His presentation as the Son of God. The only important thing is to know that He was raised from the dead some time before His presentation. The early Church writers were unanimous in their belief that He was raised early on Sunday morning, but this is not the essential point.
The point is that the wave-sheaf offering was always held on a Sunday, and that this began seven Sabbath cycles. They are called "seven Sabbaths" in the law (Lev. 23:15), and yet they begin on "the day after the Sabbath." Obviously, the law was speaking of two different Sabbaths, one on Saturday, and the other on Sunday.
The Saturday Sabbath, as I showed, was based upon Passover. The Sunday Sabbath was based upon the presentation of the Son to the Father, followed by Pentecost.
Whereas one remembers Christ's Death (Passover), the other remembers Christ's Resurrection, Presentation, and the giving of the Holy Spirit on Pentecost. The Pentecostal Sabbath marks the transition into God's Rest, which is associated with the Jubilee and the Feast of Tabernacles. The disciples in the upper room in Acts 2 overcame the lack of faith found in their forefathers at Mount Sinai, where they refused to hear God's voice in Exodus 20:18-21. The 120 disciples overcame where Israel failed.
This greater Faith brought about a greater Kingdom. Even so, Pentecost was not meant to be the final result, nor could it fulfill the provisions of God's Rest. God's Rest is discussed in Heb. 4:10,
"For the one who has entered His rest has himself also rested from his works, as God did from His."
This is set forth more fully in Isaiah 58:13,
"If because of the Sabbath, you turn your foot from doing your own pleasure [work] on My holy day, and . . . speaking your own word."
God's Rest, then, is manifested by Jesus Christ Himself, who did nothing but what He saw his Father do, and said nothing except what He heard His Father say. It is not about idleness, but about ceasing from one's own works and words. This is God's Rest, and anyone who does this has entered God's Rest. Everything they do and say springs from the position of REST. It is all a Rest-work. This is the ultimate meaning of a Jubilee, where all bondage ceases.
The Sabbath-day Rest, then, is designed to give us a first-level type of Rest. The Sabbath-year Rest increases the scope and depth of the release and Rest. The Jubilee brings it to the highest level of God's Rest, where we cease permanently from doing and saying anything that is not in accordance with the heart and mind of God.
The first and eighth day of Tabernacles are also Sabbaths. It may be that when this feast is fulfilled historically, while the overcomers have entered God's Rest, the rest of the believers will begin to commemorate seven-day rest cycles with a new starting point, based upon the first and eighth day of Tabernacles. If so, the reason would be to draw attention to the goal of all believers--to enter God's Rest, even as the overcomers have done.
If so, it would indicate another change in the Sabbath, based upon divine laws that are not yet clarified.