Cameron Douglas and Michael Douglas. Douglas has been arrested for drug offenses at least three times. In 1999 he was found with cocaine in Manhattan and was arrested and charged with a misdemeanor possession of a controlled substance. The charge was dropped after he pleaded guilty to the lesser charge of disorderly conduct. In 2007 he was charged with felony possession of a controlled substance after police officers found a syringe with liquid cocaine in a car he was in. On July 28, 2009, Douglas was arrested by the Drug Enforcement Administration for possession of 0.5 pounds of methamphetamine. Due to the large amount of the drug seized, Douglas was charged with intent to distribute. The charge carries a minimum prison sentence of 10 years and a maximum of life. On January 27, 2010, Douglas pleaded guilty to both conspiracy to distribute drugs and to heroin possession after his girlfriend had smuggled heroin hidden inside an electric toothbrush and passed it on to him while he was under house arrest. On April 20, 2010, Douglas was sentenced to five years in prison for both possessing heroin and dealing large amounts of methamphetamine and cocaine out of a New York hotel room. In October 2011 Douglas pleaded guilty to possessing drugs in prison. On December 21, 2011, he was sentenced to an additional 4-1/2 years in prison for this charge. In January 2013 Douglas was again found to have drugs in his system while in prison in Loretto, Pennsylvania.
15. Diandra Douglas received $45 million after she split with Michael Douglas in 2000. FILE-Actor-director Michael Douglas and his wife Diandra arrive at the second Barbara Steisand concert at the MGM Grand Hotel in Las Vegas Jan.1,1994. (AP Photo/Reed Saxon)