among other things being "full of wisdom" ((Ezekiel 28:12)) and "more cunning than any beast" ((Genesis 3:1))
he's not dumb. he's more clever than we are - we are beasts ((Ecclesiastes 3:18)) and the person of Christ isn't revealed to us except by heaven ((Matthew 16:17))
so if we think we're not stupid enough to think we can trick God into doing something He doesn't want to do, Satan is even less stupid than us. Satan may be an archetypical example of hubris, but he is not an idiot, neither is he omniscient. he did not try to overthrow God, but to be 'like Him' ((Isaiah 14:14)), he did not go after Adam directly but cleverly deceived his wife, thereby forcing Adam into choosing between her and obedience. he accused Job, not God, and he tries to corrupt the church because the Lord is incorruptible.
what we have in the testing of Christ in the wilderness is Satan probing the 'second Adam' for weakness. if Satan had known that the messiah is the LORD Himself hidden in flesh, how stupid does he have to be to be looking for weakness in the Almighty?
but i guess you have to share the 'impeccable' view of Christ to see that my way.
if you have the 'peccable' or 'low, corruptible' view of Christ, then naturally you also think that it was possible Satan could overcome Him, because you would see Satan as greater than Christ.
that's why i think what we ought to be looking for is when God reveals this to Satan -- and as i said earlier we've got 2 good candidates for that, being dispelled by Him ((Matthew 4:10-11)) or when He flattened him by speaking His Name ((John 18:6))