NEW YORK — The Douglas name – first with patriarch Kirk and later with son Michael – has always meant gold for Hollywood. But drama for the third generation of the Douglas family has occurred mostly off-screen, where Cameron Douglas has battled drug addiction and legal troubles.

In papers submitted for appeals court arguments Wednesday, prosecutors and a lawyer for Cameron Douglas have retold in greater detail than before how a man who seemed to have so many advantages in life could land in prison for a decade on a drug conviction.

The dispute is over Manhattan Judge Richard M. Berman's decision to double Douglas' five-year prison term after he committed several new drug infractions, including convincing a lawyer-turned-love interest to sneak drugs into prison for him in her bra on three or four occasions.

Berman said he had not "ever encountered a defendant who has so recklessly and wantonly and flagrantly and criminally acted in as destructive and (as) manipulative a fashion as Cameron Douglas has."

In his brief, Douglas' lawyer Paul Shechtman called the additional sentence "shockingly long," saying it "may be the harshest sentence ever imposed on a federal prisoner for a drug possession offense."

Douglas, 34, was originally accused of distributing and conspiring to distribute more than 4.5 kilograms of methamphetamine and 20 kilograms of cocaine from August 2006 until his July 28, 2009, arrest at a Manhattan hotel. At the time, he was so visibly high on heroin that he was taken first to a hospital before he was brought to court, and it was later learned he had been shooting heroin five to six times a day for five years, Shechtman noted.

He was released from custody on the condition that he remain under "house arrest" with a private security guard at his mother's apartment, Shechtman said. Within days, he persuaded his girlfriend, Kelly Sott, to smuggle heroin to him, hidden in an electric toothbrush. Once discovered, his bail was revoked and he was incarcerated. Sott pleaded guilty to a misdemeanor in a plea deal and was sentenced to the seven months she had already served.

Still, Douglas gained leniency from what otherwise could have been a mandatory 10-year prison sentence by cooperating with the government, contacting his suppliers by telephone and text messages as law enforcement agents watched. As a result, two drug suppliers were arrested and convicted. Douglas testified at the trial of one supplier.

Douglas was sentenced to five years in prison for a Jan. 27, 2010, guilty plea to narcotics distribution charges even before his cooperation was completed.

At sentencing, Berman noted that the Douglas family had staged interventions for Douglas that he had refused and that two decades of drug addiction treatment had been unsuccessful. He said it appeared incarceration had produced the longest period of sobriety for Douglas since he was 13.

However, it was learned afterward that even prior to the April 20, 2010, sentencing, Douglas had persuaded one of his attorneys – a 33-year-old associate at a law firm with whom lawyers said he also had a romantic relationship – to smuggle Xanax pills to him in prison. Shechtman said she "apparently became enamored of Cameron during frequent visits."

He admitted that he had shared the 30 Xanax pills with other inmates and that he had also smoked cigarettes, gambled, snorted substances and committed other infractions while in prison.

Shortly after testifying at the Oct. 3, 2011, trial of a drug supplier, prison staff caught Douglas with the opioid dependence medication Suboxone and a white powdery substance believed to be heroin. The prison punished him with disciplinary segregation for 11 months and canceled nearly three months of his good conduct time.

On Oct. 20, 2011, Douglas again pleaded guilty to drug possession, agreeing in a plea deal that the sentencing range should be an additional 12 to 18 months in prison. Prosecutors say that within a week of the plea, the government learned from a cooperating defendant in another case that Douglas had misled the government about how he obtained heroin while in prison.

Douglas had claimed he got it in a television room or at a church service or that he obtained the heroin by chance, picking it up off the floor after another inmate dropped it, the government said. But prosecutors say the cooperator revealed he had brought Douglas the drugs directly to his cell.

In court papers, Shechtman blamed Cameron Douglas' long history of substance abuse and growing up with little parental support.

"While still a young teenager, he drank heavily and began selling drugs after his father sharply limited snorting cocaine," he said. "He used illegal drugs to self-medicate – to ward off depression and panic attacks."

He began using intravenous cocaine at age 20 and then started using heroin so that by age 25, "his life revolved around heroin," Shechtman said.

His friends were fellow users, who gravitated to him because of his access to family money, which supported their habits, the lawyer said. His drug habit led him to be fired from a movie in which he had a minor role in 2006.

"Exasperated, his father gave him an ultimatum: enter a drug rehabilitation program or have his access to family money sharply limited. Cameron declined to enter treatment; his father carried out his threat; and Cameron turned to drug dealing to support his habit," Shechtman wrote.

Shechtman argued that the judge had gone too far with Cameron Douglas, punishing an addict for something beyond his control.

"While we recognize that many of the words that the district court used to describe Cameron's conduct – `reckless,' `manipulative,' `destructive,' – were apt, the simple truth is that Cameron Douglas is a heroin addict who has yet to shake his habit," he said.

Earlier on HuffPost:

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