What does 'the last will be first' mean?

It is Jesus's compressed summary of a pattern the Old Testament had already been running.

The saying appears in four Gospel places, each with slight variation:

"Many that are first will be last, and the last first." — Matthew 19:30

"So the last shall be first and the first last; for many are called, but few are chosen." — Matthew 20:16

"If anyone would be first, he shall be last of all, and servant of all." — Mark 9:35

"Let the greatest among you become as the youngest, and the leader as the one who serves." — Luke 22:26

Two Greek words carry the saying. πρῶτος (prōtos, G4413) means "first" — in rank, time, or position. ἔσχατος (eschatos, G2078) means "last" — at the end, furthest, lowest. Both words are spatial and temporal; neither is specifically about age or birth. Jesus picks up the pattern at a more abstract level than the Hebrew Bible had been running it.

But the pattern is the same. The Old Testament repeatedly elevates the one who shouldn't have been elevated by natural reckoning. Isaac the younger receives the covenant over Ishmael. Jacob the second-born receives the blessing over Esau. Ephraim receives Jacob's right hand while Manasseh stands at his left. David is brought from the sheep while seven older brothers pass before Samuel (1 Sam 16:11). Gideon says "I am the least in my father's house" (Jdg 6:15), and the angel says, "The LORD is with you" (Jdg 6:12). The first-born institutional order is overturned; the last-ranked becomes first in God's appointment.

Matthew's version at 20:16 makes the election-logic explicit. The phrase polloi gar eisin klētoi, oligoi de eklektoi — "for many are called, few are chosen" — binds the last-first reversal to the vocabulary of divine election. ἐκλεκτοί (G1588, "chosen") is the same root the LXX uses for Israel's election in Deut 7:6–8. Jesus is not stating a general principle of humility. He is stating the pattern the canon has been running since Genesis.

Notice the context at Matthew 20. The saying concludes the parable of the vineyard laborers (Mat 20:1–15). Workers hired at the eleventh hour receive the same wage as those hired at dawn. The first-hired grumble (v.11). The master's reply: "It is my will to give to this last worker as I give to you. Am I not allowed to do what I choose with what belongs to me?" (v.14–15). The saying is attached to what I choose. It is an election-parable, not a service-ethic parable, and the last/first saying is its moral.

Mark and Luke add the service dimension. Mark 9:35 says the first will be "servant of all" (διάκονος πάντων). Luke 22:26 places Jesus himself in the servant position at the Last Supper. The kingdom reversal is not only of rank but of role — the great is the one who serves.

Paul's 1 Corinthians 1:26–29 supplies the theological explanation: "God chose the foolish things... the weak... the low-born... so that no flesh may boast before God." The last-will-be-first reversal has a purpose. It eliminates boasting. If God chose the strong, the impressive, the first-ranked, human achievement would mirror divine calling. Choose the last, and no human position can become a basis for boasting.

One guard, already operating in the Old Testament text and preserved in the NT: smallness is not the qualifier; election is. Saul said the same thing Gideon said — "from the smallest of the tribes... my clan the least" (1 Sam 9:21) — and was rejected as king. The pattern is not "God chooses the small because smallness earns it." The pattern is "God chooses whom he chooses, and often it is the small." The last are first because God elects the last, not because being last is itself meritorious.

When Mary sings the Magnificat, she takes the entire pattern and speaks it: "He has brought down the mighty from their thrones and exalted those of humble estate" (Luk 1:52). The last-will-be-first logic is not a new kingdom ethic. It is the shape of what God has been doing since he spoke to Abraham.

For the full argument — including the Gideon paradigm, the Saul counter-case, and the LXX vocabulary bridge from Hebrew tsa'ir to Greek μικρότερος — see the study The Youngest Chosen.