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Mark 14:21 - (Jesus said) " .... woe to that man through whom the Son of Man is betrayed! It would be better for that man if he had not been born."

The Biblical record indicates that Judas started out well. So how did he end up so badly? One plausible conjecture is that he was double-minded* and that Satan used this 'open door' to draw him over to the dark side. Come to think of it, double-mindedness doesn't work in a marriage either! Let's look at some of the nuances in the life of Judas.
* The Greek phrase translated as "double-minded" literally means "double-souled." We are warned against double-mindedness in Ps 119:113 and James 1:8 & 4:8.

Pro: He started out strong - (Luke 9:1–2) Jesus called “the twelve” together, including Judas — and gave them power to cast out demons, to cure diseases, and to proclaim the Kingdom of God.

Pro: He had every reason to succeed - He walked with Jesus for three years. As a disciple he had the best teaching, the best example, and the most compelling reasons to be loyal.

Con: He had unconfessed sin in his life - Unconfessed sin opens the door to Satan. Judas gave Satan a huge foothold when he began stealing money from the collection bag. Later Satan gained a stranglehold on his life when he made a deal with the chief priests.

Con: The 'Judas Spirit' - Judas followed Jesus because it was convenient and self-serving. This is the essence of the "Judas Spirit." And it is rampant in the church today! Judas expected to obtain position and power when Jesus established His earthly kingdom. When it became clear that this was NOT going to happen, Judas bailed. If we follow Jesus mainly because of what we hope to get from Him, then we too have taken on a "Judas Spirit." And it's only a matter of time before we also betray Him.

I once asked if there was any way to make sure that I would never betray Jesus. Holy Spirit replied:

You will never betray someone you love!

That certainly works for a marriage! So it makes sense that it should work for Jesus too.