The following was written to Jacob:

What might be the greater spiritual meaning of Joseph's gifts to Benjamin?

"To each of them he gave changes of garments, but to Benjamin he gave three hundred pieces of silver and five changes of garments." (Genesis 45:22)

I know that silver always has something to do with redemption and garments with one's deeds, but I'm not quite connecting the dots here. Commentators seem to universally dismiss this as simply Joseph's affection for Benjamin and at most connect it to the number "5" which they believe is the biblical number for "grace". But since I don't believe such details are merely given as window dressing to the story, I was wondering what you thought.

Jacob responds:

To the best of my understanding we must begin with the Christological significance of Benjamin's name in Hebrew, "Son of the Right Hand", as Jesus (Yeshua) is "The Son of The Right Hand". "Five", however, is the number of Torah, that is the "Pentateuch", having its structural literary counterpart in the New Testament's four gospels and the Book of Acts which is essentially the sequel to Luke's Gospel.

You are correct in the typology of silver as representing the cost of redemption and that garments are, as Isaiah calls them, "The Garments of Salvation", also referred to as "Robes of ‚   Righteousness", "Wedding Garments", and raiment washed in the paschal blood, etc.

The underlying concept is that in fulfilling the requirements of the Pentateuch perfectly, Jesus "” ‚  The Son at The Right Hand of God (whom Benjamin typifies and foreshadows in this respect), by the redemption He purchased (represented by silver) affords the garments of righteousness in place of the Five Books of Torah , that is "The Law" which Paul the Apostle (also not coincidentally ‚  himself a Benjamite) says imputes the sin from whose consequences we are redeemed and that necessitate the garments in the first place.

Be that as it may, we must additionally recall that Joseph first testified about the sin of his brothers (in a foreshadowing of Christ), but this did not include Benjamin ‚  who was not yet born. Jacob, the father, would send his innocent son, Benjamin, the son of the right hand ‚  as the ransom for his brothers "” ‚   thus the silver.

I hope this helps. Being honest, I would not, however, attribute much to the speculative conclusion that "5" represents "grace", but it certainly represents the Pentateuch typologically (e.g. as in the five loaves and seven fish, and the five stones of David, etc.).