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Among his contributions are the translation of a large number of Tibetan texts, the introduction of the Vajrayana teachings to the West, and a presentation of the Buddhadharma largely devoid of ethnic trappings.

This decision was principally motivated by the intention to undercut the temptation of students becoming distracted by exotic cultures and dress, and by their preconceptions of how a guru should behave.

He drank, smoked, slept with students, and often kept students waiting for hours before giving teachings.

Much of his behavior has been asserted as deliberately provocative and sparked controversies that continue to this day.

Butterfield noted "disquieting resemblances" to cults, and "to be part of Trungpa's inner circle, you had to take a vow never to reveal or even discuss some of the things he did."

However, Butterfield also notes that "This personal secrecy is common with gurus, especially in Vajrayana Buddhism, and acknowledges that Trungpa's organization is anything but a cult:

"a mere cult leaves you disgusted and disillusioned, wondering how you could have been a fool. I did not feel that charlatans had hoodwinked me into giving up my powers to enhance theirs. On the contrary, mine were unveiled.

He had a number of notable students, among whom were Pema Chödrön, Allen Ginsberg, Peter Orlovsky, Anne Waldman, Diane di Prima, Peter Lieberson, José Argüelles, David Nichtern, Ken Wilber, David Deida, Francisco Varela, and Joni Mitchell who portrayed Trungpa in the song "Refuge of the Roads" on her 1976 album Hejira. Ginsberg, Waldman, and di Prima were also teachers at Naropa University.

Some important but less well-known students, whom he taught in England and in the USA, were Alf Vial, Rigdzin Shikpo (né Michael Hookham), Jigme Rinzen (né P. Howard Useche), Ezequiel Hernandez who later became known as Keun-Tshen Goba after setting up his first meditation center in Venezuela, Miguel Otaola (aka Dorje Khandro), Francisco Salas Roche, and Francesca Fremantle. Rigdzin Shikpo went on to continue Chögyam Trungpa Rinpoche's teachings from a primarily Nyingma rather than a Kagyü point of view in the Longchen Foundation.

In addition to making a variety of traditionalcontemplative practices available to the community, he also incorporated the many already-existing special interests of his students, evolving specialized teachings on how to apply a meditative approach to these various disciplines.

On September 28, 1986, Trungpa, in failing health due to the auto accident in his youth and to years of heavy alcohol use, suffered cardiac arrest, subsequent to which his condition deteriorated further, requiring intensive care at the hospital,

then at his home, and finally back at the hospital in mid-March 1987, where he died on April 4.

His wife Diana Mukpo wrote in 2006 that: "Although he had many of the classic health problems that develop from heavy drinking, it was in fact more likely the diabetes and high blood pressure that led to abnormal blood sugar levels and then the cardiac arrest".

However, when asked in a November 2008 interview, "What was he ill with? What did he die of?," his doctor Mitchell Levy replied, "He had chronic liverdisease related to his alcohol intake over many years."

One of his nursing attendants reports that in his last months, he suffered from the classic symptoms of terminal alcoholism and cirrhosis, yet continued drinking heavily.

She adds, "At the same time there was a power about him and an equanimity to his presence that was phenomenal, that I don't know how to explain."

He is reported to have remained in a state of samādhi for five days after his death, his body not immediately decaying and his heart remaining warm.

The way you can struggle with this is to be supported by something, something you don't know. As we are humanbeings, there must be that kind of feeling. You must feel it in this city or building or community. So whatever community it may be, it is necessary for it to have this kind of spiritual support.

You may criticize him because he drinks alcohol like I drink water, but that is a minor problem. He trusts you completely. He knows that if he is always supporting you in a true sense you will not criticize him, whatever he does.

One of the reasons that people were in his circle was that they were willing to be honest and direct with him.

He definitely was not one of those teachers who asked for obedience and wanted their students not to think for themselves. He thrived, he lived, on the intelligence of his students. That is how he built his entire teaching situation.

From my perspective, I could always be pretty direct with him. Maybe I was not hesitant to do that because I really trusted the unconditional nature of our relationship. I felt there was really nothing to lose by being absolutely direct with him, and he appreciated that.

He began drinking occasionally shortly after arriving in India. Before his coming to America, Trungpa drove a sports car into a joke shop in Dumfries, Scotland.

While his companion was not seriously injured, Trungpa was left partially paralyzed. Later, he described this event as a pivotal moment which inspired the course of his teachings. Some accounts ascribe the accident to drinking. Others suggest he may have had a stroke. According to Trungpa himself, he blacked out.

Trungpa walked in tipsy and sat on the edge of the altar platform with his feet dangling. But he delivered a crystal-clear talk, which some felt had a quality – like Suzuki's talks – of not only being about the dharma but being itself the dharma."

However, in some instances, he was too drunk to walk, and had to be carried. Also, according to the Steinbecks, on a couple of occasions his speech was unintelligible. One woman reported serving him "big glasses of gin first thing in the morning."

Two former students of Trungpa, John Steinbeck IV and his wife, wrote a sharply critical memoir of their lives with him in which they claim that, in addition to alcohol, Trungpa used $40,000 a year worth of cocaine, and used Seconal to come down from the cocaine.

Although he had not gone through the several years' worth of study and preparatory mind training required, Merwin was insistent he attend, and Trungpa eventually granted his request – along with his girlfriend as well.

At seminary the couple stayed to themselves.

At the Halloween party, after many, including Trungpa himself, had taken off their clothes, Merwin was asked to join the event, but refused.

On Trungpa's orders, his Vajra Guard forced entry into the poet's locked and barricaded room; brought him and his girlfriend, Dana Naone, against their will, to the party; and eventually stripped them of all their clothes, with onlookers ignoring Naone's pleas for help and for someone to call the police.

The next day Trungpa asked Merwin and Naone to remain at the Seminary as either students or guests.

They agreed to stay for several more weeks to hear the Vajrayana teachings, with Trungpa's promise that "there would be no more incidents," and Merwin and Naone's assertion that "it would be with no guarantees of obedience, trust, or personal devotion to him."

They left immediately after the last talk. In a 1977 letter to members of a Naropa class investigating the incident, Merwin concluded,

My feelings about Trungpa have been mixed from the start. Admiration, throughout, for his remarkable gifts;

and reservations, which developed into profound misgivings, concerning some of his uses of them. I imagine, at least, that I've learned some things from him (though maybe not all of them were the things I was 'supposed' to learn) and some through him, and I'm grateful to him for those.

I wouldn't encourage anyone to become a student of his. I wish him well.

Author Jeffery Paine commented on this incident that "[s]eeing Merwin out of step with the rest, Trungpa could have asked him to leave, but decided it was kinder to shock him out of his aloofness."

However, he also notes the outrage felt in particular by poets such as Robert Bly and Kenneth Rexroth, who began calling Trungpa a fascist.

Conducts the first annual Kalapa Assembly, an intensive training program for advanced Shambhala teachings and practices. Conducts the first DharmaArt seminar. FormsAmara, an association of health professionals.