Notice how that actual meaning of the '70 weeks' - which corresponds with when Daniel was actually written - is hived away as a side point:
The Essenes, widely thought to have been a Jewish monastic sect, taught that two Messiahs would appear toward the end of 490 years, but we cannot be certain that the Essenes based their calculations on Daniel’s prophecy. Even if they had done so, it is hard to imagine how the Jews in general would have come to be influenced by the chronology of such a reclusive group.
In the second century C.E., certain Jews believed that the 70 weeks covered the period from the destruction of the first temple in 607 B.C.E. to the destruction of the second temple in 70 C.E., while others connected the fulfillment of the prophecy with the Maccabean period of the second century B.C.E. So there was no clear consensus as to how the 70 weeks should be counted.
Applying the '70 weeks' to Jesus is a later Christian invention.
'Messiah' (literally "anointed one") was after the 7 weeks, and is Cyrus (compare Isaiah 45:1), who (according to the Bible) issued 'the word to restore Jerusalem' in 538, 49 years (7 weeks of years) after it was destroyed in 587. (This significant period contrasts with the 'nothing' year of 406BCE selected by the Watch Tower Society for the end of the '7 weeks'.)
'Leader' is not the same person as 'Messiah', despite many English translations ignoring the original Hebrew grammar, and refers to Aristobulus in the 2nd century BCE, who was 'cut off' by Jannaeus.
There's no good reason why Jews would be 'awaiting the Messiah' around 29CE as more likely than any other period.