The Gospel Writers did us no favors when they discovered Iscariot as a traitor only after the fact. In a more psychologically determinative age, they might have given us more than the bare bones description of Iscariot as the Betrayer.
Still, if we take the text seriously, as we must, the two most definitive vignettes of Iscariot both contain some reference to money. In Luke 12, he presents his concern about the use of costly oil to anoint Jesus' hair, while the actual Betrayal itself has thirty pieces of silver as one of its central elements.
Money is not evil in and of itself. As a means to an end money is quite good. As an end in itself, greed (money love; the love of stuff) excites evil. As recently as the 1960's, conservative economists like Milton Friedman worried about the coming end of scarcity in the world, as it would tend to blur the lines between the social classes. You decide if scarcity is ended in our world. My point is the use of gain as the appropriate line of demarcation between "classes" of humans demonstrates the gravitational pull of greed.
Iscariot, as faithfully portrayed in the Gospel writers, is the kind of hypocrite who uses the people he loves. We have an underdeveloped character study of Iscariot. There are volumes written on Brutus and Booth, on Oswald and Sirhan, but little is actually known about the Betrayer, the Great Assassin. We should note that at Iscariot's greatest stress point, after the arrest and mock trial of the Christ, Judas tries to return the money he has taken, as though that will somehow assuage his guilt.
He is a hypocrite, a poseur forced naked into the light of day in this case. A liar hates to be caught in his lie, a thief in his thievery, a murderer in his murder. Forced to confront his lie, the liar offers some minor technicality, the thief declares his need, the murderer cries foul against the victim. The fact the hypocrite, the liar, the thief and murderer must excuse their state when confronted convicts the criminal of his guilt more than any jury could do.
Iscariot, the Hypocrite is a dithering blunderer. He accomplishes his immediate goal but immediately repents of his act, if not of the forces that push his labored soul to act. He is the Hypocrite who makes honest men make two sets of plans; one plan to use if he tells us the truth and stays with it and a second plan to use when he lies. Apparently, Jesus trusts Judas to keep only the darkest mission of his heart. He knows his man.
Might we say it is in our own best interest to give up our hypocrisies, most particularly in reference to people we love (or, at least, count as friends?). The hypocrite is a manipulator and there is no one more consistently lame than the consistent manipulator. You cannot count on him for much but you can count on him to play the hypocrite. You cannot trust his smile, even less his tears, but you can trust his greed. You just have to find what he wants and lead him along a parallel path, always near his desire but never quite able to touch it. He will follow you to he leaps off a precipice to his own downfall.
Leadership can help overcome hypocrisy. The kind of leadership able to dispel the hypocrite must bring truth to bear on the manipulator. The leadership we need must itself be the Truth (the Christ) or, at least, must be leadership that inquires deeply into truth and comes to some mature conclusions. The truth-dealing leader must be a person with some holy curiosity, if one counts curiosity as holy fear. Holy fear is the imminent self-doubt that breeds humility. The self-doubter will first question his own conclusions before he proceeds against others, lest he, having come so far, should let slip his own salvation.
There is a hypocrite who uses the people he loves. His name is Iscariot.