Matthew 27:50 "And Jesus cried out again with a loud voice and yielded up His spirit." Matthew 27:52 "The tombs also were opened. And many bodies of the saints who had fallen asleep were raised." Matthew 27:53 "...and coming out of the tombs after His resurrection they went into the city and appeared to many." All ESV
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It is seems to me that the saints, here mentioned, must have come "out of the tombs" AFTER Christ’s resurrection. This would seem to be biblically "necessary", since Christ had to be, and WAS the "first fruit". Paul specifically identifies Christ as "first fruits". [I Cor 15 20 &23] I believe that Christ’s resurrection was the embodiment of all of the first fruit offerings, prescribed under the Law. One conundrum may be raised by this "conclusion". What about the 3 others that Jesus had previously "raised from the dead"? [Lk 7:15, Mk 5:42 & Jn 11:44] I think the answer to this conundrum is that those 3 subsequently lived until they eventually "passed on", naturally, which differentiates them from Christ.
My understanding is that when Christ died, the graves opened and the saints rose from their graves. Interestingly enough, these saints were not in heaven with God or enjoying eternity in Abraham's bosom - they were dead in their graves awaiting resurrection. Between Christ rising and His ascending, the saints went into the city and appeared to many. The Bible doesn’t say who these saints were but it is very possible that Jeremiah, maybe Isaiah, or John the Baptist could have been among them. This assertion is also supported by Psalm 68:18 and Ephesians 4:8 where it refers to leading "captivity captive". These resurrected saints were taken to heaven when Jesus went to heaven as firstfruits with Christ (1 Cor 15:20).
I think they were raised when Christ died. I am a grammarian and the grammar supports my view: Even though it sounds very strange, Matthew locates the raising of the bodies of the saints at the death of Jesus, and their coming out of the tombs and entering Jerusalem after the resurrection. The phrase “after his resurrection” (μετὰ τὴν ἔγερσιν αὐτοῦ) does not naturally modify “many bodies of the saints were raised” — as if the bodies of the saints were raised only after Jesus’s body was raised. Rather, it most naturally modifies “having come out of the tombs... they entered the holy city” (καὶ ἐξελθόντες ἐκ τῶν μνημείων μετὰ τὴν ἔγερσιν αὐτοῦ εἰσῆλθον εἰς τὴν ἁγίαν πόλιν): “... and having come out of the tombs after his resurrection they went into the holy city.” John Piper It seems that the Lord, in His great kindness, permitted these saints to see with their very own eyes the salvation He had secured for them at such great cost. Perhaps that’s why these disciples woke from death when Jesus died, and why they left their tombs when the Savior left His (Matt. 27:52-53). They were invited into the waiting—that long Saturday when all hope seemed lost—so that when Jesus appeared on Sunday morning, these who had also experienced the grave would be among the first to herald His glorious resurrection, a fitting assignment for men and women who had trusted Him in both life and death. Charles Stanley Mt 27:52. And the graves were opened; and many bodies of the saints which slept arose—These sleeping saints (Th 4:14) were Old Testament believers, who—according to the usual punctuation in our version—were quickened into resurrection life at the moment of their Lord's death, but lay in their graves till His resurrection, when they came forth. JFB
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