Rabbi Shmuley Boteach enjoyed (and sometimes suffered through) a rare privilege in 2000 and 2001: he sat down with pop legend Michael Jackson to record intimate, revealing conversations about his private and public life. Some 30 hours of taped discussions between the two are the basis for The Michael Jackson Tapes, which Boteach released after Jackson’s death in 2009. According to Boteach, Jackson made the tapes for the express purpose of publishing them in book form for the public.

Jackson befriended Boteach after being introduced to him. A renowned relationship expert, spiritual guide, much-published author of (at least 21 books to date), syndicated columnist, host of TLC’s Shalom in the Home and former love/marriage/parenting expert on Oprah and Friends, Boteach soon found himself embraced as a counselor and friend by Jackson. He was able to ask piercing questions about Jackson’s relationships with close family members, the allegations of child molestation that hounded him in the latter years of his life, his ways of coping with enormous fame, the source of the pain that finally consumed him on the eve of a huge concert series, and his views on topics such as faith, marriage, childrearing, personal responsibility toward the world and so on. The answers were sometimes shocking and often heartbreaking.

Boteach notes early in the book that Jackson’s and his intention in recording the interviews was to introduce the real man to a public who largely perceived him as a freak—a hugely talented one, but a freak just the same. Boteach writes, “America had to read our conversations and learn about the real Michael Jackson. They had to understand he was never a freak. He was not born to be weird. Rather, fame—his drug of choice—and a rudderless life had destroyed him completely.”

According to the author, Jackson’s principal tragedy was mistaking public attention for love. Jackson told Boteach early in their talks that he wanted success and fame because he wanted to be loved, yet the hero-worship that surrounded Jackson left him a lonely, isolated man. He confused soul pain with physical ailment, writes Boteach, and self-medicated with a host of prescription drugs that couldn’t heal the troubled soul.

Jackson wasn’t abandoned by those who truly loved him, Boteach emphasizes in the book. His mother, close friends, Boteach himself—all tried to help lead him out of his pain through love. One of Jackson’s great mistakes, says the author, was to listen to those who told him that he was fine, that his money was his to lavish as unwisely as he wished, that no one was in a position to lecture or limit the “king of pop.” Ultimately, Boteach removed himself from Jackson’s inner circle because the singer refused to follow the course of action they had agreed upon together; he continued to seek the counsel of sycophants who benefitted from his largesse, in the author’s eyes. (Boteach himself had refused to let Jackson carry out extreme gestures such as opening a famous toy store one day for a private shopping expedition for Boteach’s children, telling them they could have anything and everything they chose in the store.) But before the two parted company, Boteach identified key issues he believed challenged Jackson in his quest to be happy:

Messiah complex: Jackson believed he was somehow different from “ordinary” people and thus not subject to the rules of right and wrong that governed others’ lives. He could justify irresponsible spending or sharing a bed with someone else’s child that other, less-elevated people couldn’t understand, in his own way of thinking, says Boteach.

Drug use: The entertainer’s drug abuse lasted for years and was possibly more severe than most of his retinue recognized, says Boteach. Like Elvis Presley, Jackson turned to painkillers and other drugs for relief from injuries and chronic physical ailments, but the physical problems may have been covers or even substitutes for the deeper emotional and mental anguish from which both stars suffered. Boteach posits that the only way a truly loving father (which, he writes, Jackson was) could dangle his baby over a balcony in Berlin was because he was in an altered state; this event was just an instance of Jackson’s behavior meriting the “Whacko Jacko” title bestowed on him in the British press.

Unhealthy attitudes toward women and pornography use: According to the tapes, Jackson told Boteach that many women were motivated by financial interests and that some of his brother’s wives had “torn the close-knit bonds of the Jackson family asunder” out of greed. As a young boy, Jackson sang in strip clubs and may have been traumatized by seeing women perform striptease acts, thus developing a distaste for adult sexuality and perhaps for overtly sexual women. Because Jackson’s trial for child molestation charges revealed that he apparently was heavily into pornography, and because porn tends to dehumanize women, Boteach surmises that Jackson had very few healthy relationships with women, trusted very few, and was unable to connect in a healthy romantic relationship with a woman despite his stated desires to do so.

Pedophilia charges: Boteach states strongly that he never saw any evidence to convince him of the pedophilia charges against Jackson. The performer’s closest confidante and aide, Frank Cascio, maintained throughout the well-known child molestation trial that Jackson was innocent, and Boteach vouches for Cascio’s integrity in his book. Boteach and his family actually stayed at Neverland Ranch when one of the accuser’s families was there, and the author saw no evidence of foul play.

This roughly 200-page book is filled with transcripts of conversations between the author and Jackson as well as Boteach’s musings on whether Jackson had successfully overcome some of his personal foibles by the end of his life. Written with seemingly deep and genuine affection and grief at the tragic death of his former friend, The Michael Jackson Tapes is an intimate, sometimes surprising look into quiet talks between one of the world’s most famous personalities and his spiritual mentor. The author’s dedication of the book to Jackson’s children is, perhaps, a fitting dedication to the world at large that never really knew the man behind the mask:

“To Prince and Paris,
who were my children’s playmates, and
Blanket whom we never met.

“May you be inspired by your father’s virtue,
be cautioned by his excess,
and be the living fulfillment of his unrealized dream
of Healing the World by living lives of selflessness,
kindness and compassion.

“God watch over you and protect you always.”