Anna Nicole Smith had lesbian affair with son’s girlfriend

Anna Nicole Smith’s doctor has revealed his bizarre relationship  with the star – including his sordid nightclub encounter with the Playboy model that almost landed him in prison.

In 2009 Los Angeles doctor Sandeep Kapoor was charged with illegally prescribing drugs to Smith, who died of a drug overdose in 2007.

Kapoor was cleared of all charges, but at the trial his relationship with the former Playmate of the Year was called into question, when pictures emerged of a topless Kapoor kissing Smith.

Now the doctor has revealed exclusively to DailyMail.com the story of that night and the shocking events around her death, in his new book, Trust Me, I’m a Doctor.

Anna Nicole Smith died of a drug overdose in 2007. The 39-year-old was found surrounded by 1,500 prescription pills. Now her doctor Sandeep Kapoor, who prescribed her some of the medication, has revealed their bizarre relationship

Kapoor  was charged in 2009 with illegally prescribing drugs to Smith but was cleared of all charges. But during the trial it was revealed that Kapoor thought Smith could 'ruin me' after celebrating gay pride with her followed by a wild club night later. Pictured: Smith and Kapoor (right in blue) during West Hollywood's Gay Pride Parade in 2005 

Kapoor was charged in 2009 with illegally prescribing drugs to Smith but was cleared of all charges. But during the trial it was revealed that Kapoor thought Smith could ‘ruin me’ after celebrating gay pride with her followed by a wild club night later. Pictured: Smith and Kapoor (right in blue) during West Hollywood’s Gay Pride Parade in 2005 

Other pictures emerged of a shirtless Kapoor nuzzling Smith's neck at a nightclub. He said: 'I was making out with Anna, my patient, blurring the lines. I gave her methadone, Valium'. Kapoor is now revealing his experiences with the star in his new book, Trust Me, I'm a Doctor

Other pictures emerged of a shirtless Kapoor nuzzling Smith’s neck at a nightclub. He said: ‘I was making out with Anna, my patient, blurring the lines. I gave her methadone, Valium’. Kapoor is now revealing his experiences with the star in his new book, Trust Me, I’m a Doctor

Kapoor writes that he had been treating 39-year-old Smith once a month for over a year, prescribing her Valium and methadone for her back pain, when in June 2005 she invited her doctor to a Gay Pride parade in West Hollywood.

‘When I met her she was in her prime, she was thin again,’ said Kapoor. ‘And she was also medically doing pretty well. She was set on course by the doctor before me, I just had to kind of take on the reins and keep her doing well.

‘The Gay Pride was an invitation from her, she knew I was openly gay and that I had been involved with Project Angel Food, delivering food to AIDS patients, so I was very happy to support her at the pride,’ said the doctor.

‘At the last minute she said, “come on, come on the float with me”.

‘I was flattered by the invitation, Anna Nicole was a gay icon at the time, part of me was honored and liked the fact she was in the spotlight, I can’t say I wasn’t star-struck,’ he said.

Kapoor was photographed wearing a t-shirt with the slogan “Trust me, I’m a doctor”, and sat next to his patient in a Saab convertible, cruising at the front of the Pride parade.

Kapoor said Smith was ‘reveling in the tsunami of attention, blowing kisses and shaking her ample boobs.’

‘On the back of that convertible with a big-celebrity, surrounded by paparazzi and tens of thousands of cheering, screaming, partying fans, I was on top of the world,’ wrote Kapoor.

After drinking bottles of Cristal champagne with Smith in her limo, Kapoor went to an after party at the famous West Hollywood nightclub The Abbey.

Kapoor (pictured during the trial in 2010) had been treating Smith for over a year, prescribing her Valium and methadone for her back pain. He said: 'She had suffered from pain from various surgeries. She had gotten on a good regime of methadone and Valium to combat the pain'

Kapoor (pictured during the trial in 2010) had been treating Smith for over a year, prescribing her Valium and methadone for her back pain. He said: ‘She had suffered from pain from various surgeries. She had gotten on a good regime of methadone and Valium to combat the pain’

Smith's autopsy showed the drugs that caused her death were chloral hydrate combined with Benadryl, clonazepam, diazepam and lorazepam

Kapoor (left and right) was cleared of any wrongdoing and said: 'I didn't feel my treatment was wrong'

Smith’s autopsy showed the drugs that caused her death were chloral hydrate combined with Benadryl, clonazepam, diazepam and lorazepam. Kapoor (left and right) was cleared of any wrongdoing and said: ‘I didn’t feel my treatment was wrong’ 

‘My adrenaline was still pumping, and I also felt the effects of far too much Cristal champagne on an empty stomach,’ Kapoor said.

Carried away by the drunken and debauched night, surrounded by topless dancing men, Kapoor decided to bend the rules of his patient-doctor relationship to a breaking point.

According to court documents, a video taken that night ‘showed Dr. Kapoor and Anna Nicole Smith in a reclined position in a nightclub-type setting. Dr. Kapoor had his shirt off, his arms was around Anna Nicole Smith, and he was kissing and nuzzling Anna Nicole Smith’s neck.’

Kapoor says he then threw up on cushions at the back of the club, but avoided getting caught by the club bouncers.

The next day he recounted the experience in his diary, worried that he had crossed a line.

‘I was making out with Anna, my patient, blurring the lines. I gave her methadone, Valium,’ he wrote. ‘Can she ruin me?’

The words would come back to haunt him, when two years later the starlet’s body was found at the Seminole Hard Rock Hotel and Casino, surrounded by 1,500 prescription pills.

The autopsy showed the drugs that caused her death were chloral hydrate combined with Benadryl, clonazepam, diazepam and lorazepam.

‘She had suffered from pain from various surgeries. She had the implants, various things that went wrong in the past, so also had pain in her back,’ said Kapoor. ‘She had gotten on a good regime of methadone and Valium to combat the pain.’ 

Kapoor said: 'They found that one page which had to do with Anna Nicole Smith. They looked at it like it was a smoking gun, an admission of "Can she ruin me?" and could she take me down and I could lose everything' 

Kapoor said: ‘They found that one page which had to do with Anna Nicole Smith. They looked at it like it was a smoking gun, an admission of “Can she ruin me?” and could she take me down and I could lose everything’ 

Kappor's two co-defendants in the case, were Smith's boyfriend and lawyer Howard Stern (right) and her physician Dr Khristine Eroshevich (center). Prosecutors alleged Smith was a drug addict and that the three conspired to feed her addiction with illegal prescriptions 

Kappor’s two co-defendants in the case, were Smith’s boyfriend and lawyer Howard Stern (right) and her physician Dr Khristine Eroshevich (center). Prosecutors alleged Smith was a drug addict and that the three conspired to feed her addiction with illegal prescriptions 

Smith’s previous doctor had written the reality TV star prescriptions under a pseudonym, Michelle Chase, for ‘privacy reasons’ so Dr Kapoor continued doing the same.

This aroused police suspicions, who believed the drugs were unlawfully prescribed. Soon after Smith’s death, they raided Kapoor’s house looking for evidence.

Officers found medical records for Smith hidden in a stack of shirts in Kapoor’s bedroom closet. They also took his diary, hoping it would reveal clues to help build their case.

‘They took 800 pages of my diary,’ said the doctor. ‘It was a personal, horrible experience — you don’t expect the government to read it and then publish extracts from it.

‘They found that one page which had to do with Anna Nicole Smith. They looked at it like it was a smoking gun, an admission of “Can she ruin me?” and could she take me down and I could lose everything.’

Kapoor was charged with eight felonies in 2009, including unlawfully prescribing controlled substances, obtaining fraudulent prescriptions and conspiring to furnish controlled substances.

He had two co-defendants in the case, Smith’s boyfriend and lawyer Howard Stern, and her physician Dr Khristine Eroshevich.

Prosecutors alleged Smith was a drug addict and that the three conspired to feed her addiction with illegal prescriptions.

‘They made up a whole conspiracy with the boyfriend Howard Stern and the physician,’ said Kapoor.

He said prosecutors tried to make out that his diary entry ‘was a direct admission of guilt that I was involved.’

Smith was a former Playmate of the Year for Playboy and got her first big break when she posed for the magazine's cover in 1992. Pictured: Smith with Hugh Hefner in 2003

Smith was a former Playmate of the Year for Playboy and got her first big break when she posed for the magazine’s cover in 1992. Pictured: Smith with Hugh Hefner in 2003

In another startling revelation from his new book, Kapoor said Smith had a lesbian affair with her son Daniel's girlfriend in 2006, sparking an estranged relationship before they made up 

In another startling revelation from his new book, Kapoor said Smith had a lesbian affair with her son Daniel’s girlfriend in 2006, sparking an estranged relationship before they made up 

‘It certainly was bad judgment that day. And certainly I probably would not have done it in hindsight,’ said the doctor.

‘What I was saying was wrong was just the act of hanging out with her and making out with her. I didn’t feel my treatment was wrong,’ he said.

Kapoor was cleared of all charges and was praised as a ‘very conscientious doctor’.

‘It was six not guilties. Six knives pulled out of my back,’ he said, adding he is now ‘absolutely’ at peace with his treatment of Smith, and feels he did not contribute to her death in any way.

Though Stern and Eroshevich were convicted of conspiring to provide an addict with drugs, the courts later overturned Stern’s conviction and reduced Dr Eroshevich’s felony fraud conviction to a misdemeanor with a $100 fine and a year’s probation.

Kapoor was crippled by a $1.5m legal bill, but said he felt ‘relieved’ and ‘vindicated’.

‘When you’re brought to the darkest edge or the worst fear known to man that you’re gonna lose everything, including your children and your livelihood,’ said Kapoor, ‘When you come that close and the truth wins, you get so much inner confidence from that, it makes you a better physician.’

In another startling revelation from his new book, Kapoor said Smith, a former Playmate of the Year, had an affair with her son Daniel’s girlfriend in 2006.

‘Apparently, Daniel met a girl that spring, began dating her, and introduced her to Anna,’ said Kapoor. ‘The girl fell in love with Anna, and the two of them had a brief sexual relationship. It was downright Shakespearean.’

Daniel, 20, was furious when he found out. ‘He felt betrayed and stopped speaking to Anna,’ said Kapoor.

Smith's son Daniel (pictured together in 2004) was also one of Kapoor's patients and died of an drug overdose in 2006. Kapoor said Smith was wracked with guilt, believing Daniel got the drugs from her prescriptions

Smith’s son Daniel (pictured together in 2004) was also one of Kapoor’s patients and died of an drug overdose in 2006. Kapoor said Smith was wracked with guilt, believing Daniel got the drugs from her prescriptions

Daniel died three days after the birth of his half sister, Dannielynn Birkhead (pictured with her father Larry in 2016). Smith died just months later

Daniel died three days after the birth of his half sister, Dannielynn Birkhead (pictured with her father Larry in 2016). Smith died just months later

The mother and son reconciled a few months later, and in September 2006 Daniel set out on a trip to visit her in the Bahamas.

But tragedy struck when the next day the 20-year-old, who was also one of Kapoor’s patients, died of an accidental drug overdose.

The doctor said Smith was wracked with guilt, believing Daniel got the drugs from his mother’s prescriptions.

‘Daniel overdosed on methadone, which was her methadone,’ Kapoor said. ‘That grief and guilt never left her.

‘In a sense they did reconcile and they worked out those issues about this girlfriend,’ said Kapoor. ‘But it worked out the day before he died… Anna really wanted him to come to the Bahamas and live there, but he died the same day he got there.’

The death coincided with a bitter custody battle over Smith’s newborn girl, Dannielynn Birkhead.

‘After Daniel died everything went to hell for her,’ said Kapoor. ‘He died in a hospital room where she just gave birth to a baby girl.

‘She wanted to bury Daniel there in the Bahamas but I pleaded for her to come back, I knew she needed therapy. She needed to be taken care of from a psychiatric and medical standpoint.

‘Then the paternity suit comes up and they’re trying to take the baby. She spiraled out of control.’

The Los Angeles doctor is revealing his experiences with the star in his new book, Trust Me, I'm a Doctor

The Los Angeles doctor is revealing his experiences with the star in his new book, Trust Me, I’m a Doctor

‘That was a turning point for her. She died months after that. It was a very difficult time for her, she didn’t have the strength or the ability,’ he said.

Kapoor says he dropped Smith as a patient a few months before her death because she refused to move back from the Bahamas to Los Angeles.

‘I told her if you don’t come back to Los Angeles, I can’t continue to treat you or to even offer advice to you,’ he said. ‘She said, “So you’re abandoning me at my worst time?” It was very hard.’

Despite her overdose, Kapoor agrees with the judge in his court case that Smith was not an addict.

‘I think she had bouts of misuse; I think abuse and misuse are something confused,’ he said.

When a video of a pregnant and apparently stoned Smith in clown makeup emerged, it fueled rumors of her drug addiction. But Kapoor says she may have been acting.

‘You wonder [if she was high] but then you say was that a stupid prank or some kind of a joke,’ he said.

Kapoor also said there were medical reasons behind Smith slurring her words when she appeared at the 2004 American Music Awards.

‘She didn’t eat. She had a seizure that day but she didn’t want to disappoint, so she went on with it,’ he said.

Even after his torrid and tragic experience with the reality TV star, Kapoor said he still remembers Smith fondly.

‘She was a stunning woman, more so in person, physically, very tall and kind of empowering. Very much in control of her person, who she is,’ he said.

‘She worked her way up from nothing and was able to be successful. She was one of the first people to have a reality TV show.

‘I saw it at the gay parade, the cameras came on and she did this little voice, and then when the cameras were off, she went back to normal. It seemed to me she played off being that bimbo, the blonde bombshell, that was part of her shtick.

‘She presents herself as happy and giggly and very smiley. She was very easy to meet and was mesmerizing in that sense.’  

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