Hi albeto,
If it’s not offensive, Merry Christmas! I hope you and your family had a wonderful Christmas and are having a joy-filled Christmas season.
- The Bible and Sacred Tradition are silent about whether Jesus tried to dissuade Judas or not.
- Therefore, we have to make our own judgment.
- Jesus is God, so he could have stopped Judas (or whomever) from betraying him / killing him.
- Betraying / killing would cause heavy burden / eternal punishment, so Jesus should have stopped him.
- However, Jesus needed to be sacrificed so it makes sense that he chose not to stop Judas.
That's a fair summary. Well done, carry on. 
Thanks, albeto.
#4 is where we disagree, and I think our differing ideas on free will and the value of the individual determining their own future is the source of our difference. As we’ve been doing, I’ll continue with the teachings of the Catholic Church. (CCC nos. 1730-1742) God places enormous value on us making our own choices. From being made in his image and likeness we can determine our own actions based on reason and will. He calls us to choose Him (Sir 15:14-20) and allows us to choose otherwise.
Isn’t that how a good parent would behave? As my children grew older they had to make their own choices in more areas. They knew the good choices. If they made bad choices, then they accept the consequences. I don’t force my will upon them. If my son, God forbid, were to get involved in drugs and end up in jail, my heart would be ripped apart, but those are his choices. I would not lock him in his room or similar in order to stop him from that behavior.
However, according to you, that would be the appropriate behavior for me. Jesus should have forced his will upon Judas to stop him from betraying Jesus. You argue that the negative consequences Judas (or others) would experience outweigh the submission of their freedom, and that God should have made the choice for him, or, in other words, controlled his behavior. With your explanation of “freedom,” that can make sense because your description is in actuality not freedom.
If, as according to your description, my behavior is rooted in biology and history, then I am not free to choose my own future. In fact my future was essentially chosen before I was even born, and, taking that thinking to its logical conclusion, before anyone was born! Where we are today and where we will be in the future was written in the stuff of the Big Bang.
For this reason we can interpret Judas' actions as logical according to what he would have understood to be logical.
Well . . . maybe . . . regardless, though, logical doesn’t mean right.
First, Judas knew the difference between right and wrong. He was able to make his own choices and was responsible for those choices. He did not have autism or dementia.
Next, Judas chose to be a disciple of a teacher. This demands a particular relationship between the two, not unique to Jesus, which includes obedience. For a disciple to betray the teacher would be a terrible wrong. Today we may not think that way, but back then everyone would have thought that.
Finally, Judas was with Jesus, his teacher, for three years. He heard and saw the same things that the other eleven Apostles heard and that the women heard and that the many other disciples heard. He saw the miracles of healing, forgiveness of sins, walking on water, bringing back to life. He heard Jesus teaching about repentance, mercy and the Kingdom of God. He knew that Jesus was here to fulfill the Law. He knew that Jesus taught love of God, love of neighbor, and love of enemy. He heard Jesus’ command to love others as Jesus has loved them. That command implies a stronger, deeper love of Jesus for everyone that Judas would have experienced constantly in those three years. To betray someone who loved you that much is clearly wrong in any time and place.
But Judas wanted something other than what his teacher, who loved him completely, wanted or taught. People suggest that it was money or political upheaval, though those motives don’t seem to make much sense. Whatever it was, it was something that Judas wanted regardless of what his master wanted, or what the people would think.
If he wasn't fully intent on doing the second greatest sin ever (killing god), then his despair was unjustified.
That statement seems unjustified to me. People fall into despair and kill themselves over a lot less than killing God. Getting his teacher, who loved him very much, killed certainly could do it. Unfortunately, Judas did not believe in God’s mercy. He thought that his sin, whatever it was in his mind, was something that God could not forgive. If he had believed in God’s mercy, taught and demonstrated many times by his teacher, then he might have still kept the office of an Apostle.
How could Jesus have let him take that course, knowing the future and the intimate thoughts of Judas as he would?
I think we see now that our different understandings of free will are the source of our differences in answering this question. You see less value in individual freedom and responsibility, and that forcing someone to do something for their own good is acceptable. Of course, the logical extension is that becoming robotic slaves is okay as long as we are happy. I see that our individual freedom and responsibility is a gift from God and whether we are happy or not depends upon the choices we make.
I don’t think we have to agree on how to answer the question, but I think we can agree on how and why we don't agree.