It's worth pointing out again, that the term "crazy wisdom" in English, with its Tibetan equivalent term "ye shes chol ba" are both inventions of Chogyam Trungpa. The Tibetan term does not exist in any Tibetan works, nor is it a term that is used by Tibetan teachers in Tibet, either in the past or the present.
His Holiness the Dalai Lama has also pointed out this fact, that it doesn't exist as terminology in the Indo-Tibetan traditions of Vajrayana.
The way I see it, is as a term, it is best used only within the context of Chogyam Trungpa's teachings, and not anywhere else, as there is no context outside of Chogyam Trungpa, to use this term.
Instead what people may be thinking about when they think about "crazy wisdom yogis", are very advanced yogis who deliberately engage in unconventional conduct, which is permitted by their gurus, due to at a minimum having attained the stage of strong heat on the path of application (in a Vajrayana context) or the path of seeing. At that point in time, for such a yogi, engaging in unconventional conduct, will act as fuel to the fire that burns away their afflictions even faster.
But nowhere does this mean they will abuse and hurt sentient beings physically, sexually, or psychologically. Never.
As for wisdom being crazy, this is an oxymoron. Wisdom, or ye shes, is very far away from crazy. If anything is crazy, it is sentient beings, who are led astray by the delusion of dualistic vision 24/7 365.
"The Guru is the Buddha, the Guru is the Dharma,
The Guru is the Sangha too,
The Guru is Śrī Heruka.
The All-Creating King is the Guru."
-- The Secret Assembly Tantra