But apart from the concept that there are physical gates to heaven, what is the ontological explanation for why these OT just could not enter heaven? They were lacking SOMEthing.
I was always taught that there were 2 reasons why the OT just could not enter heaven. The first reason is sound - the OT just had to wait in Limbo until Christ opened the gates of heaven on Ascension Thursday. Christ, being the Redeemer and Reconciler of man with God, was the only one, and the first one, to re-enter heaven. Christ was a new-Adam, who conquered Original Sin.
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The second reason, which is speculative, is that the OT just had to be baptized. Even St John the Baptist, who was part of the Old Law, said that Christ would Baptize with the Holy Ghost. And another reason would be that Christ would provide them the Holy Eucharist, but this is also speculative. Would God require all of the OT Just to enter the Church (the perfect, fulfilled Church of the New Law) before entering Heaven? I don't see why not. But I also can't say for sure.
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Recall that curious episode where the Gospel speaks of how the dead were raised to life after the Resurrection? Why? Was it just to create a spectacle? Some of the Church Fathers held that they were temporarily raised from the dead to be baptized.
This also explains what Our Lord mean when saying that St. John the Baptist was the greatest person "born of woman" but lesser than the least in the Kingdom of God (those born again of water and the Holy Spirit). We are talking about a division here between the natural (natural virtue, etc.) and the supernatural REbirth inito the Kingdom (the "crowning" of St. Ambrose).
Even Our Lady, who was full of grace, who never sinned, still needed a Redeemer. She still called Our Lord Her Savior. But if She was free from sin (the most justified person ever), why did She still need to be baptized? Because She still did not have the baptismal character fully. The Old Law was imperfect; it was a precursor; it was incomplete. Christ completed the Old Law and the Holy Ghost started the Church on Pentacost. Thus, it stands to reason, that to get into heaven under the New Law, you had to be baptized, receive the Eucharist, and become a perfect member of God's new kingdom.