Shkreli, who seemed relaxed and looking like his physique filled out a bit since his jailing, said nothing out loud during the hearing and kept what was – for him, at least – a relative poker face.
However, when a prosecutor suggested that one of the defense's arguments was "preposterous," Shkreli arched his eyebrows and turned to make a smilingly devilish face at another of his lawyers, Marc Agnifilo.
Also Friday, Matsumoto reserved ruling on the question of the amount of money Shkreli should forfeit to the federal government when he is sentenced.
Prosecutors want Shkreli to fork over $7.36 million. They also want him to set aside assets that include a one-of-a-kind Wu Tang Clan album and pricey artwork to secure that penalty during his planned appeals of his conviction.
Matsumoto has refused to release Shkreli's bond despite his incarceration because of the possibility that she will apply the $5 million toward a forfeiture she orders.
Brafman, as he has in the past, argued during the hearing that Shkreli's case is rare, if not unique, since all of the investors in his hedge funds, which ended up going bust, actually ended up with much more than their initial money back, after he launched Retrophin and paid investors back with cash and company stock.
"All of these people made substantial money back at the end of the ordeal," Brafman argued.
Brafman noted that Shkreli did not use the money from hedge fund investors to "support a lavish lifestyle," but instead created a legitimate drug company, which was financed in part by money from one of the hedge funds.
But assistant U.S. Attorney Alixandra Smith argued that Shkreli fraudulently concealed the awful performance of his funds to make it seem that he was a successful hedge fund manager.
Smith also said Shkreli "frittered away" investor money that ended up in Retrophin by buying Jay-Z concert tickets, and paying for cab rides and meals for himself.
Additional reporting by Meg Tirrell