Well here is why, context.

This is not a prophecy, this is a lamentation. If you read all of Psalm 22, it is clearly a lament over a loss of feeling of the presence of a divine being. The Psalmist here is lamenting that God seems to be ignoring him while he goes through these hard times. The Psalm goes on about how God isn’t answering prayer, yet Israel still loves him, how God is letting him be hurt and punished, and more. The piercing of hands and feet is merely one of many symbolic images used by the Psalmist to convey this.

For example the Psalmist also says:

“12 Many bulls surround me;
strong bulls of Bashan encircle me.
13 Roaring lions that tear their prey
open their mouths wide against me.
14 I am poured out like water,
and all my bones are out of joint.
My heart has turned to wax;
it has melted within me.
15 My mouth is dried up like a potsherd,
and my tongue sticks to the roof of my mouth;
you lay me in the dust of death.”

Now I think we can all agree that nowhere in the Gospels or in any supposed Messianic prophecy does Jesus get surrounded by bulls of Bashan, lions, dislocated at all bones, heart turned to wax, or anything similar.

The problem is that you are taking a literary device, imagery, and trying to turn it into something that it isn’t: prophecy.

Just because piercing of hands and feet happen within an imagined and symbolic passage, that does not make it in any way a prophecy. Especially within the context of the Bible, given that Israelite prophecies portrayed in the Bible come as direct revelations from God or from his angels, generally they begin with a phrase like “The Lord says” or declaring what will happen. Nowhere in the Psalm is the writer claiming that these will be future events. The Psalmist is using imagery to evoke how lonely and broken he feels. He is talking about himself, not about the future.

So the easiest way to debunk your argument is merely that you are taking that out of context. The Psalmist is talking about himself in a symbolic sense. Not about a future person.

I’d add, that there are numerous reasons throughout the Old Testament why one can dismiss the idea that Jesus was the prophesied Messiah (read Deuteronomy through).

I would somewhat argue with that notion. The reason being is that the vast majority of people were illiterate, especially in regards to Hebrew (given that only even 3% of Jews were literate in their own language).

The likelihood of them seeking comfort in any text is doubtful, given they couldn’t even read the text. Thus, it would have only been the tiny few who could read who would be doing this. The problem there is that, these few who could read most certainly were very attentive to context. The people who wrote and edited the Gospels, the Pauline Epistles, etc they all show a decent amount of knowledge of the Hebrew Scripture, and utilize the Hebrew Bible with quite a lot of knowledge of the context, they merely are very adept at twisting the meanings and such.

I’d add that they probably didn’t have that many problems, given how the Greek Septuagint (which is what they most likely would have been using, given the whole of the New Testament appears to have been written in Greek) mistranslated Isaiah 7:14, where the word ‘almah in Hebrew means “Young Woman”, but the Greeks rendered it parthenos which means “virgin.”

This rendering within the LXX (which is what most Christians of the age would use, given that Hebrew was a liturgical language having been completely supplanted by Aramaic, and Greek) would easily justify the Christian prophetic beliefs.