This expression was spoken by the Lord Jesus on three occasions. We shall see that the first two occasions are lessons for believers and the third is a solemn lesson for unbelievers.

In Matthew 19:28-30 we read: “Then Peter answered and said to Him (Jesus), ‘See, we have left all and followed You. Therefore what shall we have?’ So Jesus said to them, ‘Assuredly I say to you, that in the regeneration, when the Son of Man sits on the throne of His glory, you who have followed Me will also sit on twelve thrones, judging the twelve tribes of Israel. And everyone who has left houses or brothers or sisters or father or mother or wife or children or lands, for My name’s sake, shall receive a hundredfold, and inherit eternal life. But many who are first will be last, and the last first.” In this passage the Lord is promising believers a future reward. He specifically promised His Twelve disciples that they would sit on “twelve thrones judging the twelve tribes of Israel.” But then He speaks to all believers who have been willing to forsake family and country in order to follow Him and He promises them a present and a future blessing. They would “receive a hundredfold,” which refers, I believe, to their being received into “hundreds of Christian homes” where they can enjoy Christian fellowship instead of merely enjoying fellowship with their immediate family at home. They are also promised “eternal life,” which speaks of their “enjoying eternal life in heaven” according to the measure of devotion they had to Christ in this present life. (Eternal life in this passage does NOT mean they didn’t possess eternal life here on earth, nor does it mean we gain eternal life by following Christ, for eternal life is gained and possessed the moment we trust in Jesus Christ as our Savior…see John 3:16 and 5:24). The Lord then closes by issuing a warning to believers who may have such high thoughts of themselves and their devotion to Christ that they believe they deserve the highest and best rewards. So He says, “But many who are first will be last, and the last first.” In short, He is saying, “If you think you are the best disciple and deserve FIRST PLACE, you may end up having the LAST PLACE, and the one who you looked down upon or didn’t even notice, may end up having the FIRST PLACE when it comes to rewards.

In Matthew 20:1-16 the Lord tells a parable of a landowner hiring workers in his vineyard to illustrate this and another truth. He hires people at the beginning of the day and they agree to a certain wage (verses 1-2). With each passing hour he hires more workers but instead of promising them a certain wage he simply tells them, “You also go into the vineyard, and WHATEVER IS RIGHT I WILL GIVE YOU” (verses 4 & 7). At the end of the day he paid them their wages, “beginning with the last to the first” and each man was PAID THE SAME AMOUNT. Those who were hired first complained because they had worked ALL DAY and RECEIVED THE SAME PAY as those who worked PART OF THE DAY (verses 10-12). The landowner then said, “Friend, I am doing you no wrong. Did you not agree with me for a denarius? Take what is yours and go your way. I wish to give to this last man the same as to you. Is it not lawful for me to do what I wish with my own things?” (verses 13-15). The Lord then said, “So the last will be first, and the first last.” What is the main lesson here? Much like the first lesson from the preceding chapter, some believers think they deserve more rewards than others because THEY SERVED THE LORD LONGER. But the Lord, who is Sovereign, can and will give believers the rewards He chooses, not based on “how long they served,” but rather on “their faithfulness and devotion to Him.” Those who think they will be “FIRST in line” to receive the best rewards will find they LAST in line” to be rewarded.

In Luke 13:24 the Lord Jesus said to a group of Jews, “Strive to enter through the narrow gate, for many, I say to you, will seek to enter and will not be able.” He is speaking in this verse of entering the “gate that leads to eternal life in heaven” (see Matthew 7:13-14 along with John 10:9 & 14:6). He then warned them that there were many of them who will refuse to enter through that gate, trusting rather in their good works (see verses 25-27 with Matthew 7:21-23) to them to heaven. In verses 28-29 he teaches them that they will experience “weeping and gnashing of teeth” (in hell….Matthew 8:12; 13:42, 50; 22:13; 24:51 and 25:30) while believers in Christ from the Jewish nation and from Gentiles nations around the world will “sit down in the kingdom of God.” And then He says, “And indeed there are last who will be first, and there are first who will be last.” I believe those words teach us that there are Jews, who considered themselves as FIRST (as God’s favored nation) will be LAST (rejected and cast into hell due to their unbelief), while many Gentiles, who they considered to be the LAST (people that God would never bless), will be FIRST (sitting down in the kingdom of God enjoying His eternal blessings).  (420.5)  (DO)