What does Jesus mean by generation when talking about the end times?

Eschatology makes hypocrites of us all. The most figurative book in the Bible is interpreted literally, and literal texts are interpreted figuratively to meet our preconceived expectations, making a secondary issue into one of the most incendiary.

Using methods of sensus plenior

Matthew writes in a Hebrew form similar to poetry, but has nothing to do with rhyming. Passages are linked by repeating words and ideas. In chapter 5 Jesus goes up the hill, and mentions the poor in spirit and the meek. In Chapter 8 he comes down the hill and heals a leper and converses with the meek Centurion. This pattern ABC...abc... is repeated four times in Matthew, the last one beginning with chs. 23 and 28.

By examining the parallel passages, Matthew teaches an alternate eschatology where "this generation" can be taken literally which is different from Preterism.

Religious leaders work to be seen of men

   23:5 But all their works they do for to be seen of men:

   28:5 But they said, Not on the feast day, lest there be an uproar among the people.

Humble shall be exalted

   23:12 And whosoever shall exalt himself shall be abased; and he that shall humble himself shall be exalted.

   28:13 Verily I say unto you, Wheresoever this gospel shall be preached in the whole world, there shall also this, that this woman hath done, be told for a memorial of her.

Judas worse than the Pharisees

   23:15 Woe unto you, scribes and Pharisees, hypocrites! for ye compass sea and land to make one proselyte, and when he is made, ye make him twofold more the child of hell than yourselves.

   28:15 And said unto them, What will ye give me, and I will deliver him unto you? And they covenanted with him for thirty pieces of silver. ...24 The Son of man goeth as it is written of him: but woe unto that man by whom the Son of man is betrayed! it had been good for that man if he had not been born.

Crucified

   23:34 Wherefore, behold, I send unto you prophets, and wise men, and scribes: and some of them ye shall kill and crucify; and some of them shall ye scourge in your synagogues, and persecute them from city to city:

   28:26 And as they were eating, Jesus took bread, and blessed it, and brake it, and gave it to the disciples, and said, Take, eat; this is my body. 27 And he took the cup, and gave thanks, and gave it to them, saying, Drink ye all of it; 28 For this is my blood of the new testament, which is shed for many for the remission of sins.

Jesus going away

   23:39 For I say unto you, Ye shall not see me henceforth, till ye shall say, Blessed is he that cometh in the name of the Lord.

   28:29 But I say unto you, I will not drink henceforth of this fruit of the vine, until that day when I drink it new with you in my Father’s kingdom.

He is coming

   24:3 And as he sat upon the mount of Olives, the disciples came unto him privately, saying, Tell us, when shall these things be? and what shall be the sign of thy coming, and of the end of the world?

   28:32 But after I am risen again, I will go before you into Galilee.

Beginning of sorrows

   24:8 All these are the beginning of sorrows.

   28:38 Then saith he unto them, My soul is exceeding sorrowful, even unto death: tarry ye here, and watch with me.

Love wax cold

   24:12 And because iniquity shall abound, the love of many shall wax cold.

   28:40 And he cometh unto the disciples, and findeth them asleep, and saith unto Peter, What, could ye not watch with me one hour?

His gospel

   24:14 And this gospel of the kingdom shall be preached in all the world for a witness unto all nations; and then shall the end come.

   28:45 Then cometh he to his disciples, and saith unto them, Sleep on now, and take your rest: behold, the hour is at hand, and the Son of man is betrayed into the hands of sinners.

The abomination of desolation

   24:15 When ye therefore shall see the abomination of desolation, spoken of by Daniel the prophet, stand in the holy place, (whoso readeth, let him understand:)

   28:48 Now he that betrayed him gave them a sign, saying, Whomsoever I shall kiss, that same is he: hold him fast.

The kiss of Judas is the abomination that causes the removal of the Son of Man from the world. How much more desolate could the world be?

Pr 12:22 Lying lips are abomination to the LORD: but they that deal truly are his delight. Pr 17:15 He that justifieth the wicked, and he that condemneth the just, even they both are abomination to the LORD.

Flee

   24:16 Then let them which be in Judaea flee into the mountains:

   28:56 But all this was done, that the scriptures of the prophets might be fulfilled. Then all the disciples forsook him, and fled.

Tribulation

   24:21 For then shall be great tribulation, such as was not since the beginning of the world to this time, no, nor ever shall be.

   28:67 Then did they spit in his face, and buffeted him; and others smote him with the palms of their hands,

The greatest tribulation that ever has or will occur is the tribulation of Christ. He who knew no sin, was made to be sin... What would have happened if Christ died before he got to the cross? If the days of his tribulation had not been shortened, no one would be saved.

The desolation

They traded Christ for Barabbas.

   24:23 Then if any man shall say unto you, Lo, here is Christ, or there; believe it not.

   28:21 The governor answered and said unto them, Whether of the twain will ye that I release unto you? They said, Barabbas. ...31 And after that they had mocked him, they took the robe off from him, and put his own raiment on him, and led him away to crucify him.

Sun darkened

   24:29 Immediately after the tribulation of those days shall the sun be darkened, and the moon shall not give her light, and the stars shall fall from heaven,

   28:45 Now from the sixth hour there was darkness over all the land unto the ninth hour.

Shaking

   24:29...and the powers of the heavens shall be shaken:

   28:51 And, behold, the veil of the temple was rent in twain from the top to the bottom; and the earth did quake, and the rocks rent;

Watching

   24:30 And then shall appear the sign of the Son of man in heaven: and then shall all the tribes of the earth mourn, and they shall see the Son of man coming in the clouds of heaven with power and great glory.

   28:65 Pilate said unto them, Ye have a watch: go your way, make it as sure as ye can.

Gathering of saints

   24:31 And he shall send his angels with a great sound of a trumpet, and they shall gather together his elect from the four winds, from one end of heaven to the other.

   28:19 Go ye therefore, and teach all nations, baptizing them in the name of the Father, and of the Son, and of the Holy Ghost:

This generation

24:34 Verily I say unto you, This generation shall not pass, till all these things be fulfilled.

If Matthew is suggesting that all this was fulfilled at the cross, 'this generation was truly 'this generation'. But we must look at the parallel between watching for him in the sky and guarding the grave. It is suggestive that the rapture occurs at the moment of death.

We must rethink our concept of time. If eternity is not just a long time, but the absence of time, then we can die and leave 'time' at different times, but arrive in eternity simultaneously. Jesus can come as a thief in the night as one drops dead in the field and another taken in sleep, yet in their experience they immediately and simultaneously arrive with Christ in eternity.

Every generation which reads "this generation" is this generation. They all see the rapture at the moment of death. We all meet him in the air together.