Caleb, I appreciate the positive feedback and honest disagreement. However, Isaiah 53 doesn’t suggest a crucified messiah; the servant of God is identified with Israel it seems.

The Jewish people did not believe in a crucified, dead, and then resurrected messiah even in Jesus’ time, but one that completely triumphs (cf. John 12:33–36).

I think it is best to understand the interpretive quotations of the apostle and Jesus (and the Fathers) as being typological/anagogical (aka allegoresis) rather than grammatical/authorial (aka normal exegesis).