23 Then Jesus looked around and said to His disciples, “How hard it is for those who have riches to enter the kingdom of God!”
24 And the disciples were astonished at His words. But Jesus answered again and said to them, “Children, how hard it is for those who trust in riches to enter the kingdom of God!
25 It is easier for a camel to go through the eye of a needle than for a rich man to enter the kingdom of God.”
26 And they were greatly astonished, saying among themselves, “Who then can be saved?”
27 But Jesus looked at them and said, “With men it is impossible, but not with God; for with God all things are possible.”
28 Then Peter began to say to Him, “See, we have left all and followed You.”
29 So Jesus answered and said, “Assuredly, I say to you, there is no one who has left house or brothers or sisters or father or mother or wife or children or lands, for My sake and the gospel’s,
30 who shall not receive a hundredfold now in this time—houses and brothers and sisters and mothers and children and lands, with persecutions—and in the age to come, eternal life.
31 But many who are first will be last, and the last first.”
Also found in Matthew 19:23-30 and Luke 24-30.
The disciples were astonished when Jesus pointed out how difficult it is for a rich man to enter the kingdom, for it was the prevalent opinion in Judaism that riches were a mark of divine favor, as with Job. — Guthrie, page 873.
Jesus (v.23) wasn’t saying that a rich person couldn’t be saved. He was saying that it was difficult for a rich person to be saved because that person would usually trust in riches for his well-being and see his wealth as evidence that God was already pleased with him.
Children, how hard it is (v.24) — [Jesus] repeats His hard saying, and this time removes His qualifying reference to the rich: “it is hard in any case, though specially hard for such.” The words “For them that trust in riches” are an addition to the text here [and not in the original manuscripts]. — Wuest, page 205.
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Hereupon the disciples perceived what was more alarming still, that not alone do rich men trust in riches, but all who confound possessions with satisfaction, all who dream to to have much is to be blessed, as if property were character. — Chadwick, page 283.
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eye of a needle (v.25) — Some teach that the needle’s eye here refers to a gate in the wall of Jerusalem through which by means of much pulling and pushing a camel could finally be taken. The Greek of Matthew 19:24 and of Mark speaks of a needle that is used with threat, and that of Luke 18:25, uses a medical term for the needle used in surgical operations. It is evident that the gate is not meant, but the tiny eye of a sewing needle. This was probably a current proverb for the impossible. … It is therefore impossible for anyone whose love or riches keeps him from trusting the Lord Jesus as Savior, to be saved. — Wuest, page 205.
greatly astonished (v.26) = struck out of self-possession
with men it is impossible, but not with God (v.27) — Take your stand beside man on the question of riches, and it is impossible to be saved. but, take your stand beside God on the matter, and the formerly impossible becomes possible. — Wuest, page 206.
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Peter said “We abandoned all.” The verb is aorist, speaking of a once for all act. The “we” of course are the Twelve. Peter and John left a lucrative fishing business, and Matthew, a rich source of income from his tax-collector’s office, to become the disciples of a poor itinerant preacher. Peter’s question was in effect, “What reward will we get for having become poor for your sake?” The spokesman of the disciples showed by his question that they were still thinking in terms of material rather than spiritual riches. — Wuest, page 206.
followed you (v.28) — Tense indicates a once-for-all, irrevocable decision.
now in this time (v.30) — in the Dispensation of Law
in the ages to come (v.30) — in the Millennial Kingdom
The Dispensation of Grace had not been revealed at this time (and would not be until God revealed it to Paul), so it is not treated in this passage in any way.
As for “many who are first will be last, and the last first,” my commentaries have nothing to say. I believe it means that many who hold positions of power and who seem to be big shots on earth will have no place in the Kingdom or will, at best, get in by the skin of their teeth, so to speak. While others, who live life of quiet, humble service to the Lord will receive many blessings in the Kingdom.