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According to believers in an intermediate state between death and the resurrection:

And he said to him, “Truly, I say to you, today you will be with me in paradise.” [Luke 23:43 ESV]

  • Did Jesus preach to spirts in prison in Sheol?

18 For Christ also suffered once for sins, the righteous for the unrighteous, that he might bring us to God, being put to death in the flesh but made alive in the spirit, 19 in which he went and proclaimed to the spirits in prison, 20 because they formerly did not obey, when God's patience waited in the days of Noah, while the ark was being prepared, in which a few, that is, eight persons, were brought safely through water. [1 Peter 3:18-20 ESV]

  • If the answer is yes to both questions, how can we reconcile the two facts? Did Jesus visit different compartments of Sheol? Were the "spirits in prison" in paradise?

Relevant questions:

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  • +1 Is the tension here merely in the use of 'prison' vs. 'paradise' to describe (perhaps) the same thing? Feb 10, 2022 at 18:17

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In Catholic theology, there are 4 "compartments" / "parts" of the underworld where souls are waiting in the Intermediate State (see Wikipedia article Limbo):

  1. Hell of the Damned, where the wicked OT people go as well as NT people who die in the state of mortal sin.
  2. Limbo of the Patriarchs, aka sheol, aka "bosom of Abraham", where the righteous OT people went. But they couldn't yet enter Purgatory / Heaven until redemption by Jesus Christ made it possible. This is where Jesus go to preach to "spirits in prison". This place should be empty now.
  3. Limbo of Infants: where the unbaptised infants go, who are too young to have committed actual sins but not freed yet from original sin (through baptism).
  4. Purgatory: where Christians who die in the state of grace (no mortal sin) go, but still have venial sins to be purified.

The Catholic Answer article Did the good thief go straight to heaven? leaves open two possible final destination of the thief:

  1. Straight to heaven due to his perfect contrition for his sins (thus, similar to saints).
  2. To purgatory first, which is the antechamber of heaven, a state more blessed than in the first 3 compartments of the underworld above, as souls undergoing purification are assured of their eternal salvation.

CONCLUSION: Jesus definitely went to the Limbo of the Patriarchs to preach to the "spirits in prison". One interpretation is that "paradise" means this place, where Jesus's presence made the place a paradise. The thief thus went together with Jesus to the Limbo of the Patriarchs because at that point the gates of heaven would not have been opened yet until the resurrection. After resurrection, the thief may then go to heaven (or purgatory?) while Jesus came back to earth for 40 days (having been resurrected) to show himself to the apostles, to teach them, and to appear to hundreds more people before ascending to heaven.

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