Jesus was talking about the generation that would be alive at the end of the Age when the signs of His return will be seen. That's the context.
I believe Jesus is contrasting "this generation" as a beginning of those who bring forth eternal life unto all the nations of the world as they proclaim the Gospel in the power of the Holy Spirit. The fig tree, like the good olive tree representing Jews of faith, the chosen from Israel foreknown of God, a remnant according to election of grace (Ro 11:1-). This elect remnant though few in number during the time of Christ, are not the full number of the remnant because Paul writes there were in the days when Elijah prayed to God, seven thousand who had not bowed the knee to Baal. (Ro 11:4) These Old Covenant faithful saints represent the spiritual Kingdom of God on earth before the coming of Christ. And once the Gospel is sent out there will be many more Jews that turn to Christ in faith during this age of Gospel grace.
These Old and New Covenant believers were Jews. Back to contrasting! Who are these faithful Jewish saints of Israel contrasted with? Native born Jews of the seed of Abraham, who were never of the faithful remnant of Old or New. Listen to the words Christ uses in describing them.
Matthew 3:7 (KJV) But when he saw many of the Pharisees and Sadducees come to his baptism, he said unto them, O generation of vipers, who hath warned you to flee from the wrath to come?
Matthew 3:8-10 (KJV) Bring forth therefore fruits meet for repentance: And think not to say within yourselves, We have Abraham to our father: for I say unto you, that God is able of these stones to raise up children unto Abraham. And now also the axe is laid unto the root of the trees: therefore every tree which bringeth not forth good fruit is hewn down, and cast into the fire.
The Greek word used to define generation here is - 1081 génnēma offspring; by analogy, produce (literally or figuratively):—fruit, generation.
They are the offspring of the devil.
John 8:44 (KJV) Ye are of your father the devil, and the lusts of your father ye will do. He was a murderer from the beginning, and abode not in the truth, because there is no truth in him. When he speaketh a lie, he speaketh of his own: for he is a liar, and the father of it.
The long-winded point I'm attempting to make here, is that there are two people or generations who are of Israel, but the two are opposed to one another. The devil has been around from the beginning of creation, producing offspring by his lies, but even the Pharisees and Sadducees in the days of Christ were of his/this generation. I don't think anyone would limit the offspring of the devil to only those whom Christ was speaking directly to. Neither does He limit "this generation" that are of the blossoming fig tree to any single generation in time.
Christ tells His disciples, who live in every age that they should look for the fig tree to bear life. We see that when these first Messianic Jews faithfully followed the mandate of Christ, to preach the Gospel unto all the world. The fig tree, before being cursed to never bear life again, was a symbol of the nation of Israel. Israel was chosen to be the representation of the Kingdom of God, but only the remnant within its borders remained faithful to God unto death. Those that were faithful are the part of Israel that was never in blindness through unbelief. It is they, the remnant according to election of grace from Israel that are symbolic of the fig tree that begins to bring forth life. And every believer in every generation understands this. We are all (believers) witnesses to their faithfulness and the abundant life their proclaiming of the Gospel has brought to people who believe throughout the whole earth.
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