Jesus uses this phrase on four different occasions in the gospels: twice in Matthew - here and in Ch 20 - and once each in Mark and Luke, to teach Christians that no one should suppose that they will be placed first in the future eternal kingdom before others (CP V23-30). In answer to Peter's question in V27 as to what exactly could the disciples expect seeing that they had left all to follow Him, Jesus assured them that the blessings He gives will far outweigh any material loss or persecutions they may suffer for Him, but in His closing statement in V30 that many that are first shall be last, and the last first, Jesus warns that even those who have given up most for Him must never presume that the chief places in the future eternal kingdom are guaranteed to them (CP 20:1-16).
Jesus' discourse in Mt 20:1-16 is called the parable of the labourers in the vineyard. In it Jesus expands upon His closing statement in 19:30. Jesus teaches in this parable that salvation is by grace alone, not by merit, and everyone who responds affirmatively to God's call to salvation will have a place of honour in the future eternal kingdom. Length of service has no bearing on it - new Christians in their service to God are just as important to Him as those who have served Him the longest. No one should feel superior because of position or length of service in the church, for God is no respecter of persons. In the age to come many who held high office in the church and were thought to be great leaders will be placed behind others who held no office and were considered to be unimportant. In the future eternal kingdom every Christian will be treated according to how their works are made manifest at the Judgement Seat of Christ (CP Ro 14:10; 2Cor 5:9-10). Every Christian has to come before the Judgement Seat of Christ for their earthly works to be tried, and it is how those works stand or fall that will determine the Christian's place in Heaven (CP 1Cor 3:11-15). Every one of the earthly works we build upon the foundation of Christ will be evaluated, but only the works symbolized by gold, silver and precious stones will be able to withstand the heat of the refining fire. All lesser works represented by wood, hay and stubble will burn up. Christians will not lose their salvation if this happens, but there will be a loss of heavenly rewards (CP Lu 13:22-30). Jesus teaches us here that merely professing to know Him will not gain anyone entry into the future eternal kingdom. Only those who conform strictly to the conditions He has laid down for salvation can enter in. The Jews thought that as they were the descendants of Abraham and Isaac, etc, they would automatically enter in, but Jesus illustrates by this parable that no one can enter in who is not totally consecrated to the service of God and completely yielded to the authority of Jesus. This applies to everyone who professes to be a Christian (CP Mt 7:21-27).
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