Mat 23:32 Fill you up then the measure of your fathers.
Mat 23:33 [You] serpents, [you] generation of vipers, how can you escape the damnation of hell?

Alternative: You fulfill then the full capacity of your fathers. Snakes, offspring of vipers, flee from the judgement of the trash pit.

First, see Matt 12:34 for an earlier formulation of this same idea in this second verse, but which brings in the ideas of "worthlessness" and "beautiful" that are central to Christ's message. Snakes are only referred to as symbols of worthlessness.

These verses make a subtle connection to the beginning of this diatribe about religious leaders simply being actors. In the beginning of these verses, Christ refers to the relative worth of things: the value of the long prayer versus that of a widow's house, the value of tithes of spice against the "weight" of moral principles. Here, Christ combines that idea of physical measurement with the measurements of blood relationships. Our capacity comes from that of our forebearers. For better or worse, we stand on the shoulders of those who came before us. That capacity is passed on physically, mentally, and even spiritually in the blood of one generation to the next.

This would have been a much more familiar idea in Christ's time, when people lived closer to nature, than in today's world. Everyone then saw how the generations of animals carried forward their good and bad traits. In the less annonymous community of the past, children did not escape the communities judgment of their parents.

The Jews of Christ's time were quick to claim their relationship with the prophets, but Christ points out that the prophets were the exceptions among them. Their true parents were those who killed the prophets.

What applies to the Jews of his day applies just as readily to everyone today. We are all quick to claim the relationships we are proud of, no matter how tenuous, but just as quick to forget about the more prominent relationships that we are less proud of.

Though perhaps we suffer from a worse delusion: thinking that we are above the past, both the good and bad. We mistakenly think we can reinvent ourselves from whole cloth: creating our own personal morality. Christ knew better. What is true for us was also true of all previous generations. The only thing that has increased in recent generations is our disconnection from our forebearer's wisdom, replacing it with the fictional reality we see on television.

"Full" is plêroô , which mean "to fill," "to fulfill," and "to fill full."
"Escape " is pheugo, which means "to flee," and "to take flight."
"Damnation" is from krisis, which means "separating," "distinguishing," and "judgment."
"Generation" is gennêma, which means "that which born or produced." It means "offspring," "fruits of the earth," any "product" or "work." It also means breeding and producing.
"Hell" is from geenna, which is Greek for Gehenna, the valley of Hinnom (the Hebrew word), south of Jeruselem where trash, including diseased animals and human corpses was burned. A constant fires was kept burning there. This area was originally where children were sacrificed to Baal, and Baal (Beelzebub, "lord of the flies") is the name that Christ says others call him as the personification of evil.