I would be grateful to offer an accessible literary approach to this question, based on Matthew 26:14-6, Matthew 27, Genesis 3, and Zechariah 11
===================================
1. The roles Matthew gives to the people (λαός), Judas, and Pilate in the crucifixion, are analogous to Adam, Eve, and the Snake in Genesis.
===========
Adam (Gen.3:7) eats the fruit. Possibly ignorantly / missing the description-under-which. Ignorance of the right thing to do was the starting point for many ancient discussions of moral failure.
The λαός (Mt.27:23) are made to answer the biggest ethical question by Pilate: Why crucify him? What crime has he committed? But they answer question with exclamation. Like Adam wasn’t shown pausing for thought, the λαός don’t process it. When they say “His blood be on us and on our children” this isn’t conscience but a “Defiant and vindictive cry” (Meyer) and “whatever the consequences we are willing to suffer them” (Pulpit Commentary).
===========
Eve (Gen.3:2-7) chooses the wrong side of a dilemma between obeying God’s command and failing to “be like God”; or becoming like God and disobeying him. As an exposition of moral theory, her case would be the development of Adam’s: if they don’t gain the knowledge of good and evil, he’ll eventually eat the fruit by mistake.
Judas (Mt.26:14) also is shown making a choice. On the one hand he betrays an innocent for money, (so unlike the λαός he knows full well what he’s doing). But on the other hand after it’s too late he does process the ethical question they ignored. This might be the knowledge of good and the knowledge of evil both in operation. And Eve and Judas having wrong foresight and wrong hindsight respectively.
===========
The Snake (Gen.3:2) comes to Eve’s dilemma from outside. Its advice is the argument that a good God couldn’t punish someone for seeking to resemble him. It’s logical, but it’s detached from what matters: interfering in a relationship it isn’t part of.
Pilate (Mt.27:19) doesn’t want to execute Jesus, but he does it anyway. Where Judas realises he has betrayed innocent blood (Mt.27:4), Pilate executes Jesus and says he is innocent. (Mt.27:24). Where the Snake instigated detachedly, Pilate concludes detachedly.
===================================
2. Judas’s suicide doesn’t bode well for him!
Eve’s choice was central to the Original Sin. She accepts God’s judgement, and becomes the mother of mankind (painfully, as we are told). She is a model of repentance – she brings life from death and glory from shame.
Judas’ choice was central to the Crucifixion. He doesn’t not-judge-lest-he-be-judged, but somehow discovers the worst of all formulas: he judges himself.
In the process he provides bizarre anti-solutions to numerous of Jesus’ parables and lessons: the workers in the vineyard suddenly have a colleague who knocks off early; nearby another group of servants with some money to invest are astonished to see him throw his portion away and try to escape over the fence. Or at Mt.26:14, by approaching the Pharisees with a proposition Judas ‘threw the first stone’. From Mt.15:11, what a man eats doesn’t defile him: entailing Eve wasn’t defiled by the fruit... but evil has borne fruit within Judas.
Matthew’s discussion of repentance=μετάνοια is very brief (Mt.3:8-11), but on the basis of “Bear fruit in keeping with repentance.” that's not the fruit Judas has borne. Matthew doesn’t have the parable of the widow’s mite, but Judas’ donation of the blood money to charity both passes and fails that comparison. It passes because he gives everything he has, but fails because he leaves too early to see the money put to good use for the poor, or to stop it from ending up being spent on the dead.
We can’t be sure if suicide has the status of a mortal sin for Matthew and his readers/listeners (https://en.wikipedia.org/wiki/Suicide_in_antiquity#Bible_teachings) but where Eve brings the lives of the human race from out of the Original Sin, Judas brings nothing but his own miserable death from the Crucifixion.
Why does Judas do it?
We can discount that he betrays a man to death so he can give the money to the poor. But also Matthew shows a moral realisation in hindsight, and the sad detail of the Potters Field.
So a better question is perhaps who is the most complex Judas it could be? At Mt.10:1 he’s listed as being given the authority to cast out demons and heal every disease and affliction. And moreover at Mt.10: this expands to “Heal the sick, raise the dead, cleanse lepers, cast out demons.”
Just before he visits the Pharisees, at Mt.26:6-12 he has seen Jesus be anointed by a woman in the house of Simon the leper. It’s possible he’s disgusted, or finds it paradoxical that now, when it comes to it, a leper is cleansing Jesus.
Matthew Franck discusses what miracles Judas performed (https://www.firstthings.com/web-exclusives/2018/07/the-miracles-of-judas) and concludes “We cannot say.” and also more strongly than I will put it: “It is not our place to presume to know what may become of any of our fellow fallen creatures.”
It’s open to the reader/listener to suppose Judas thinks as do the Pharisees (whom he approaches), and with any hindsight of the later persecutions, he would be correct if he thinks to follow Jesus is going to be dangerous to his life in this world.
Is this perhaps a tragi-comic setup? Where he’s always out of the room when the dead are raised, or looking the other way when a storm is calmed… until in the end he decides it’s safer to prioritize the here-and-now, and that perhaps this is what God would want in any case.
If so, he is unpersuaded by the grammar, so I can’t identify with him!
It’s conjectured he was from Kerioth, which might be far enough south and provincial enough for some dialect barrier to have put much of the teachings beyond him.
Be sure to learn Ancient Greek!
===================================
3. And yet…
Judgement is reserved to God (Isaiah 33:22, Psalm 75:7). We cannot say what God should do about him. Matthew only mentions judgement in Mt.7:1 (judge not) and the judges at Jesus’ trial (Mt.19:28), but the parables let us fill in the gaps: e.g. Mt.18:32-35 “And in anger his lord delivered him to the torturers, till he should pay all his debt. So also my heavenly Father will do to every one of you, if you do not forgive your brother from your heart.” This is judgement from above.
It’s possible Matthew wants the gospel to have discussion points like this. And Judas seems to have always been a fertile source:-
He might have been possessed by Satan (Luke 22:3 ; John 13:27)
He might not have had a choice, the betrayal being part of God’s plan. This idea was floated as early as the 2nd Century AD, e.g. in the non-canonical Gospel of Judas (56 - ...Truly [I say] to you, Judas, those who offer sacrifices to Saklas […] everything that's evil. But you'll do more than all of them, because you'll sacrifice the human who bears me.)
Judas’ regret counts for something by Matthew mentioning it. It makes him a deeper and more realistic characterisation of sin.
He doesn’t wait to see if Jesus is found innocent, or attend the trial and attempt plead for him. He perhaps understands that this makes no difference to God (e.g. based on Mt.5:28)
Returning to Mt.19:30, the unmerciful servant is tortured but not executed
Betraying someone who will return from death and is beyond death might not matter, if the Resurrection resets that scale
Judas closes off one of the possible converses to the redemption by Christ’s blood. This idea is more of a symbol in Matthew than a system like in the NT, but it is powerfully and clearly put:-
Matthew 26:28 ~ Exodus 24:8
“for this is my blood of the covenant, which is poured out for many for the forgiveness of sin”
Judas tries to make his own answer to the Father, by pouring out his own blood. This is not the right answer (including because of Lev.22:20 Do not bring anything with a defect, because it will not be accepted on your behalf. Isaiah 59:2 But your iniquities have separated you from your God; your sins have hidden his face from you, so that he will not hear.)
But (i) the first of those is applied to Jesus’ sacrificial atonement by analogy from vows and freewill offerings, and (ii) Judas might think it’s better than nothing. That these things might have occurred to him could be argued from a need for the NT authors to address it more detail (e.g. Rom. 8:3, 1 Pet. 1:19).
- From Mt.5:30 “If your hand does you sin” he might have decided his heart or his self has done him sin.
==========================
4. The Flock Doomed to Slaughter
There is perhaps some hope for Judas in the prophecy of Zechariah (which Matthew cites, but by the name Jeremiah, at 27:9)
Zechariah 11 is a bleak story (David Baron's commentary understatedly titles it "A Dark Episode"): about a foolish shepherd (or idol shepherd) whom the Lord sends to “the flock doomed to slaughter.”
This chapter bears close reading, since by the location and prominence Matthew gives it, it is important to his conception of both Judas and substitutionary atonement.
The flock doomed to slaughter already had three evil shepherds. The new one, the narrator, fulfils God’s commands by ruining them in a month, but because of a mutual hatred he parts ways with them too soon, saying “let what is to die die” (Zechariah 11:9). He says they don’t have to pay him, but they give him thirty pieces of silver anyway, and he breaks one of his two staves, which is called “Favour”. The Lord tells him to give the money to the temple, which he does, and he decides to break the other of his two staves, which is called “Union.”
As an intertext, important enough for an explicit mention by Matthew - this fleshes out some concept of Judas as a pessimist who can understand the Lord’s vengeance on the wicked, but not his mercy to the weak.
What’s interesting for reading Judas is that the Lord doesn’t leave the shepherd of the flock doomed to slaughter. It is God who decides if his covenant is broken. Despite him breaking the staves, God still commands him: to “Take once more the equipment of a foolish shepherd.” (i.e. nothing!)
The shepherd’s mistake was to assume his role was (as Zechariah 11:6) to obey the Lord by destroying the evil shepherds, but the Lord also wanted him to supply a suppressed premise. He should have cared for the sheep even though they were doomed. The story closes with God placing this terrible pronouncement:-
Woe to my worthless shepherd,
who deserts the flock!
May the sword strike his arm
and his right eye!
Let his arm be wholly withered,
his right eye utterly blinded!
At the end of this chapter, this is superlatively bleak, but as with the punishments of the Original Sin, or Apostasy at Exodus 20:5, God is merciful.
That’s far from the worst a sword-blow can do.
So maybe, just maybe, Judas goes into the Kingdom maimed.
