Max,
I am neither an elder, nor wise, but here's my take on it, for what it is worth: It seems as if any answer to your question would necessarily verge on being speculation. That being said, the "issue" naturally presents itself to the reader of Scripture. If Satan is destroyed by the cross, and Satan is an intelligent being who was aware of the coming Seed, then why did Satan involve himself in personally bringing it about?
My speculation is that Satan's main strategy throughout the life of Christ was to deflect Him from the cross, whether through the offers of glory in the wilderness, or through the rebukes of Peter. However, once he was aware that Christ had set His face as a flint to obey the will of the Father, and that the cross
was going to happen, he undertook, in His malevolence and hatred against the Son of God, to make it as painful as possible, and to bring it about on his own.
As in, "If this is going to happen, then I'm going to make this as bad as possible, and I'm going to make sure that it hurts..."
As I recall, John Piper teaches roughly the same thing. I may have first heard it from him, actually; I can't quite remember. It's been about a year since I listened to this sermon, and I could be mistaken, but I believe it sets forth the same basic idea that I wrote above:
The Suicide of Satan
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