The Jєωs' Messiah didn't come during each of their horrible sackings after King Solomon; or after the Jєωs were scattered then brought back; or even during the wholly EVIL rule of Antiochus Epiphanes. Their Temple became so bad that the Jєωs were making up their midrash (like Bugnini scribbled down his midrash), and Jesus would eventually call it a den of thieves, but still some hung on in hope, with mostly-terrible priests, which must have been a nightmare. And then pagan Rome took over, so that even the terrible priests were unhappy and started their scheming. 1000 yrs of this crap, and prophecies, wars, Temple defacing, losing the entire Ark and Scriptures, being dragged off with hooks, tortured, etc, and THEN, the Advent happened.
We've had some bad times, I know, but we've gone only about 50 years with the darkness (BAD "Catholic midrash", aka Vatican II) overcoming the Vatican, versus the Jєωs' century+ when they had to deal the Temple priests who were all ecuмenical with pagans. But like the priests in the time of Jesus' Incarnation, while the Temple was a spiritual shambles, a few still believed (the priest Zechariah; and Simeon with his Nunc Dimittis) and just ignored and resisted the thieving priests I guess.
I asked once, why didn't God send Jesus earlier, like before Epiphanes. A priest/canon lawyer repeated what God said to Elias after he asked a similar question: that there were yet a remnant who didn't bend the knee to Ba'al that Elias apparently had no idea about. And they would have children who mostly wouldn't bend the knee to Ba'al; and maybe people would see bad stuff (like the exiles) and convert. I try to think of it as, maybe some barbaric people hundreds of years ago had to suffer rape, pillaging, and martyrdoms just so my great-great-great-grandparents could eventually be born in America, so my children and nieces and nephews could get Baptised and hope to see the Beatific Vision. And therefore what seemed like "too much misery" for them actually gave US a chance to go to Heaven (so I thank God for the graces given our forebears).
But the Bible does mention a cup being filled with the sufferings of the Saints and Martyrs, so that's a good question. In my humble opinion, the cup overrunneths. But maybe it's a far bigger cup.