You spoke of the book of Matthew, well, here are some things I see as I looked at it this morning:
Jesus predicts his death 3 times in the book of Matthew, this does NOT mean he does not allude to it at other times.
But he clearly states it 3 times in Matthew's Gospel: Matthew 16:21; Matthew 17:22; Matthew 20:17.
It is in the 3rd instance of Matthew, when it clearly shows that all twelve of the disciples (therefore, including Judas Iscariot) are informed of his coming death:
According the Gospel of Matthew, "[SUP]17 [/SUP]Now Jesus was going up to Jerusalem. On the way, he took the Twelve aside and said to them, [SUP]18 [/SUP]“We are going up to Jerusalem, and the Son of Man will be delivered over to the chief priests and the teachers of the law. They will condemn him to death.-- Matthew 20:17
I looked at the book of Matthew briefly, since you mentioned your question.
According to Matthew 16, it is only after Peter's confession that Jesus is the Messiah,
when Jesus begins speaking to his disciples about his forthcoming delivery to death.
Interestingly, while you bring up Satan's entering Judas Iscariot,
Peter was the one rebuked... as being/being influenced by Satan; when Jesus says, "Get behind me Satan."
According to Matthew's text (at least), a foolish Peter meant to save Jesus from death ("I will not let you die," or "you must not die this kind of death" type statement) -- Yet Christ said, "You speak merely of human concern."
Yet, even more interesting to me is that Christ has just told Peter, specifically:
I will give you the keys to the Kingdom of heaven.
(I mean... If someone with authority over you gives you the keys to something, do you tell them what they can or cannot do?)
Yet, right after Jesus promises to give "The Keys" to Peter, the to-be recipient asserts his "merely human"-- even satanic--
will. T
Thankfully, Christ had not yet given the keys... according to the word "will" in Matthew 16:19)
But why Judas did what he did was purely for his own profit... kind of like as Peter meant when influenced by Satan (as mentioned in Matthew 16), or you and I can slip into thinking-- if we do not keep listening for God's direction through Scripture, Spirit, and the apostles.
In the case of Peter, Christ rebuked the wrongful thinking and later forgave the denials (although, I do not know if Peter is shown to be restored in the Book of Matthew; I need to read that again).
In the case of Judas Iscariot, Christ allowed the betrayal and did not go back to him-- due in part to the timing of Iscariots self-chosen death.
But let's take it back to Matthew 16, "Who do you say I am?" Jesus asked.
Well, who is the Jesus of the Book of Matthew, of the Bible? Who is he to us today?