He played a huge part in Anna Nicole Smith's life, taking on the roles of lawyer, confidant and lover.
But on Thursday Howard K Stern (pictured) was found guilty of two counts of conspiracy for fuelling the star's prescription drug problem, one that was to ultimately kill her.
After two months of testimonies, the 41-year-old was convicted along with Anna's psychiatrist, 62-year-old Khristine Eroshevich, for conspiring to furnish prescription drugs to an addict.
Thirty-nine-year-old Anna, star of E!'s Anna Nicole Show, died of a prescription overdose in Florida in 2007.
Both Howard and Khristine are due to be sentenced on January 6 and face three or more years in prison.
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