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I have criticised the crazy wisdom idea in 
Part 2b of my essay on Integral World. As it apopears in the New Age, the Integral Movement, etc, it is a rationalisation that so-called Gurus use to justify their abusive behavior of their disciples and devotees, and/or their own weakness and lack of control in oneself.
It is however quite likely that at one time in ancient Tibet it really did mean something. So it is important not to throw the baby out with the bathwater, and disregard the idea outright. In Sufism also there is the concept of crazy wisdom, which is used in a very constructive, creative and compassionate way. They tell funny stories, for instance; the Mulla Nasruddin stories are a great example of crazy wisdom. Crazy wisdom doesn't have to mean violence and abuse.
The perversion of the crazy wisdom meme seems to have come about in the modern secular West with the coterie of abusive and narcissistic gurus who like to use it as a justification for their own lack of authentic spirituality and self-discipline. Chogyam Trungpa, Osho Rajneesh, Da Free John/Adi Da, and, to a lesser degree, Andrew Cohen, are examples of so-called "crazy wisdom" gurus. Here the term "crazy wisdom" is used by them and/or by their followers to justify substance abuse (Trungpa, Da), extreme narcicissism (Cohen, Wilber), and sexual (Trungpa, Rajneesh, Da), emotional (Da, Cohen), and financial (Rajneesh, Da, Cohen) manipulation and abuse of devotees and disciples. These activities are light years away from true spirituality and true Divinity.
  Holy Madness: Spirituality, Crazy-Wise Teachers, And Enlightenment by Georg Feuerstein;
This book explores the subject of the "crazy wisdom" adept, including an anaylisis of contemporary charismatic gurus such as Chogyam Trungpa, Bhagwan Rajneesh, Aleister Crowley, and Adi Da (who Feuerstein was adevotee of for a while and as a result seriously emotionally traumatised by, although I don't know how many of his actual experiences with Da and the Adidam community make their way into the book). While it is is one thing to consider the ambigious, crazy, narcisiistic, and inflational guru, without refernce to the Intermediate Zone, Feuerstein is no closer to the truth then Len Oakes ( Prophetic Charisma) is. It is not enough to look at the extrenal forms and personalities of the teachers, one has to explore the occult dynamics as well. Unfortunately, I haven't read this book, so I cannot comment on whether Feuerstein does actually address this issue or not.
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