Shkreli has a history of making provocative comments against specific women, the prosecutors said.
He was banned from Twitter in January for harassing a Teen Vogue writer and persisted in verbally badgering women online.
Shkreli responded to the government’s request with a profanity in a Facebook post, adding “I will never kiss their ring or snitch. Come at me with your hardest because I haven’t seen anything impressive yet."
He quickly backed off, writing an apologetic letter to the judge in a request to remain out on bail.
"Some may have read my comments about Mrs. Clinton as threatening, which was never my intention," Shkreli wrote. "I used poor judgment but never intended to cause alarm or promote any act of violence whatsoever."
Brafman vowed Shkreli would behave if the judge let him remain free until sentencing.
"Stupid doesn’t make you violent," Brafman said. "Sometimes stupid makes you stupid."
Shkreli was just engaging in political satire in his comments about Clinton, Brafman said.
The judge wasn’t buying it.
"What is so funny about this?” a visibly angry Matsumoto demanded. “He’s soliciting an assault on another person in exchange for $5,000. Under the facts and circumstances, I’m going to respectfully deny your request to change my mind. I can’t say with any certainty that the threats have not been taken seriously by anybody.”