Is Despair the greatest sin?

It can lead to:

  • "Church? I don’t need no church to tell me how to worship. I got God all figured out.
  • wounded pride, resulting in guys like me doing stupid ■■■■■
    and MY SPECIALTY
  • “I got this. I ain’t got no problem I can’t fix the easy way.”

When does confidence cross the line into pride?

I dunno. Prolly at puberty.

2 Cor 12
7
. . . . Therefore, that I might not become too elated, a thorn in the flesh was given to me, an angel of Satan, to beat me, to keep me from being too elated.
8
Three times I begged the Lord about this, that it might leave me,
9
but he said to me, “My grace is sufficient for you, for power is made perfect in weakness.” I will rather boast most gladly of my weaknesses, in order that the power of Christ may dwell with me.
10
Therefore, I am content with weaknesses, insults, hardships, persecutions, and constraints, for the sake of Christ; for when I am weak, then I am strong.

“elated” in the above is sometimes translated as “proud,” or as “arrogant.”

I don’t believe that despair is a sin at all. Furthermore, I believe that there are certain types of knowledge that simply cannot be attained without complete and utter despair.

Sorry, no. It cannot be explained with words.

Agree, but I’d change knowledge to experience.
We’re stuck between hammers of anguish and anvil of necessity - by design. Experience, like square circles is something God can’t create.