He was convicted past year of lying to investors in his hedge funds and manipulating shares a biotech company he founded. The notorious "Pharma Bro" Shkreli faced the court due to charges of security fraud from back in his hedge fund days.
"He wants everyone to believe he is a genius, a whiz kid, a self-taught biotech wonder", said prosecutor Jacquelyn Kasulis.
"Mr. Shkreli is about to turn 35 years old", she said "He is a man who needs to take responsibility for his actions".
But Shkreli staunchly defended the price in his statements to the media and on his once vibrant Twitter account, cultivating a "pharma bro" persona that was brash and outspoken. In September previous year, he took to social media to offer $5,000 for a strand of former presidential candidate Hillary Clinton's hair, a statement Matsumoto saw as a threat and ordered Shkreli to be placed in jail until he was sentenced.
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Shkreli, 34, was convicted last August after a five-week trial of securities fraud and conspiracy.
Shkreli was also booted from Twitter early past year for harassing journalist Lauren Duca.
At the start of Friday's hearing, Matsumoto noted that she has reviewed 55 letters of support provided by the defense team. Shkreli's attorney Benjamin Brafman even said at times he wished to inflict bodily harm on his own client while he argued for a light sentence.
Unapologetic from the beginning, when he was roundly publicly criticised for defending the 5,000% price increase of Daraprim - a previously cheap drug used to treat HIV - Shkreli seemed to drift through his criminal case as if it was one big joke. He told the court that he sometimes wants to hug Shkreli and sometimes wants to punch him, but that his outspokenness shouldn't be held against him. I was across the street from 9/11; I've built businesses from zero to hero, many times over. Shkreli will get credit for six months he has already spent in jail awaiting his sentencing.
"This was a witch hunt of epic proportions", Shkreli said at the time, even if "one or two broomsticks" were unearthed.
Judge Matsumoto read letters from Shkreli's family and supporters who rallied on his behalf. Still, she noted, that in a January email conversation, Shkreli allegedly wrote "f- the feds" and in other exchanges downplayed the seriousness of having to forfeit millions of dollars because of his conviction.