Well, there is another story in his book The Orthodox Heretic, which pretty much puts it plainly.
The story is called "Betrayal", and it and it's short commentary are on pages 117-119. The story is about a temple master who calls his faithful young disciple, and says that he fears the disciple will betray him. The disciple is shocked, and says that he always tries to be faithful to the master's teachings. Here are the master's words, that end the clever little story.
"But you fail to understand, my young friend." replied the Master. "The fact that you have never betrayed my teachings, and the fact that you swear never to betray them; this is to betray them already."
In his commentary, Rollins seems to keep this in the realm of human teachers. But even in that, I think it is problematic. Especially in regards to Christian teachings.
For example, Paul says to "imitate me, as I imitate Christ". Paul does not seem to take the stance that the believers were to practice some kind of "faithful betrayal", as Rollins puts it in the commentary, lest they betray him and his teachings by following them too closely. Now, Paul does seem to recognize areas for differences of opinions, for example when he deals with those who eat meat and those who don't, but he treats most of his teachings as being authoritative, and expects those he writes to to take them seriously, to follow them, and to be faithful to them.
But I think there is more to Rollin's clever little story and commentary. Perhaps I am being unfair, but I think he is going beyond mere human teachers. I think that he is saying that we can betray God by following too closely to what He says in His Word.
I could, for example, point to the story which gives it's name to the whole book, The Orthodox Heretic. In this clever little story, a man gets a message directly from God about a way to act, but he defies God, saying "I do not need the Scriptures or your words to tell me what I ought to do", and "So, my God, I defy you in order to remain faithful to you", p 97. Rather than being angry with the man, the story ends with God seeming to be rather pleased with this man's act of defiance.
I suppose the contrasts could not be more plain--the disciple in the "Betrayal" betrays the teacher by being too faithful to the master's teachings, while the man in "The Orthodox Heretic" defies God in order to remain faithful to God.
And the message could not be more plain--the rebels are the saints, the disobedient are the shining examples, the traitors are the faithful, those who shake their fists at God in defiance to His Word are those who are most pleasing to God. God doesn't want you to follow His Word, but to strike out on your own.
Again, it seems Rollins is most interested in spinning his own betrayals into having been good things. I rather suspect that, consciously or not, Rollins knows that what he teaches is against God, is against God's Word, is contrary to sound doctrine, is actually a betrayal of what God has revealed. But instead of repenting, he would rather do what is right in his own eyes, and wants to justify his ways in the eyes of the world. That is why Judas becomes a figure of courage in his clever little story, why the faithful disciples is the real traitor, why the man who stands in defiance against God is the one who is faithful to God.