In papers submitted for appeal court arguments today, 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 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.
Judge 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 offence".
Douglas (34) was originally accused of distributing and conspiring to distribute more than 4.5kg of methamphetamine and 20kg 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 the drug five to six times a day for five years, Mr Shechtman noted.
He was released from custody on condition that he remain under "house arrest" with a private security guard at his mother's apartment, Mr 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 Once discovered, his bail was revoked and he was incarcerated.