Question: Regarding your statement: “Many who are first will be last, and the last will be first”. I understand the statement Many who are first will be last, meaning many of the Jews (who knew you first) will the that last to enter Heaven because they refuse to believe and follow you.

But what did you mean by and the last will be the first?

God’s answer:

Question: So what you are saying is that this is related to what you said earlier in the earlier Chapters?

God’s answer:

Meaning: To understand God’s statement you have to read the previous chapters.

Matthew 18 (1-7)

At that time the disciples* approached Jesus and said, “Who is the greatest in the kingdom of heaven?” He called a child over, placed it in their midst, and said, “Amen, I say to you, unless you turn and become like children, you will not enter the kingdom of heaven.

Whoever humbles himself like this child is the greatest in the kingdom of heaven. And whoever receives one child such as this in my name receives me.

“Whoever causes one of these little ones* who believe in me to sin, it would be better for him to have a great millstone hung around his neck and to be drowned in the depths of the sea.

Matthew 19 (13-30)

Then children were brought to him that he might lay his hands on them and pray. The disciples rebuked them, but Jesus said, “Let the children come to me, and do not prevent them; for the kingdom of heaven belongs to such as these.” After he placed his hands on them, he went away.

Now someone approached him and said, “Teacher, what good must I do to gain eternal life?”* He answered him, “Why do you ask me about the good? There is only One who is good. If you wish to enter into life, keep the commandments.” He asked him, “Which ones?” And Jesus replied, “ ‘You shall not kill; you shall not commit adultery; you shall not steal; you shall not bear false witness; honor your father and your mother’; and ‘you shall love your neighbor as yourself.’” The young man said to him, “All of these I have observed. What do I still lack?” Jesus said to him, “If you wish to be perfect, go, sell what you have and give to [the] poor, and you will have treasure in heaven. Then come, follow me.”

When the young man heard this statement, he went away sad, for he had many possessions. Then Jesus said to his disciples, “Amen, I say to you, it will be hard for one who is rich to enter the kingdom of heaven. Again I say to you, it is easier for a camel to pass through the eye of a needle than for one who is rich to enter the kingdom of God.” When the disciples heard this, they were greatly astonished and said, “Who then can be saved?” l Jesus looked at them and said, “For human beings this is impossible, but for God all things are possible.”

Then Peter said to him in reply, “We have given up everything and followed you. What will there be for us?” Jesus said to them, “Amen, I say to you that you who have followed me, in the new age, when the Son of Man is seated on his throne of glory, will yourselves sit on twelve thrones, judging the twelve tribes of Israel. And everyone who has given up houses or brothers or sisters or father or mother or children or lands for the sake of my name will receive a hundred times more, and will inherit eternal life.

But many who are first will be last, and the last will be first.

Unfortunately, the way these chapters were compiled, there were other parables and stories in between, So the meaning of Jesus statement got lost