"This generation" could mean a generation who saw these things taking place thousands of years from when he said it. Like end times.
Most of the people he was speaking to about this (the disciples) were dead before 70 ad. So they didn't see it take place.
No. It couldn't mean that. Be careful saying that a generation will not see what Jesus said they would see.
Matthew 24:34 is the pivotal passage. "Verily I say unto you, this generation shall not pass, till all these things be fulfilled." Note again "these things."
"This generation" is defined by its earlier use in the book of Matthew. Hope this helps.
Matthew 1:17-"So all the generations from Abraham to David are fourteen generations; and from David until the carrying away into Babylon are fourteen generations; and from the carrying away into Babylon unto Christ are fourteen generations."
Matthew 11:16-"But whereunto shall I liken this generation?" The, "this generation," of this text is the "now" of Matthew 11:12. ) Matthew 12:39, 41, 42, 45 -- "An evil and adulterous generation . . . this generation . . . this wicked generation" is that era, that day, the generation of Christ's personal preaching, death, burial and resurrection (cf. Matt. 12:40,42).
The "men of Nineveh" is the generation of Jonah. The "queen of the south" is the generation of Solomon contrasted with "this generation" of Jesus.
Matthew 16:4-"A wicked and adulterous generation seeketh after a sign; and there shall no sign be given it, but the sign of the prophet Jonah." The "generation" of this passage is the Pharisees and Sadducees of Jesus' day (cf. "sign" in Matthew 16:1,4). Matthew 17:17 - "O faithless and perverse generation, how long shall I be with you?" That generation was the time Christ was "with" them.
Matthew 23:36-"Verily I say unto you, all these things shall come upon this generation. " Notice that "this generation" is distinguished from "the days of (your) fathers" (v. 30).