Federal prosecutors have asked Judge Edward Davila to sentence Holmes to 15 years in prison and a fine of more than $800 million. They argue she deserves that sentence for duping investors out of hundreds of millions of dollars by falsely claiming she had developed a revolutionary blood testing device.
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But Holmes is asking the judge for leniency. Court filings show she's requesting 18 months or less in prison or house arrest.
Will that happen?
"I think this judge has to give her some period of incarceration," Ellen Kreitzberg, a professor emeritus at Santa Clara University School of Law who has been following the case closely, told ABC7 News.
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Holmes faces up to 20 years in prison for each of the four counts of fraud. Kreitzberg thinks that won't happen either.
"I would be very surprised if the sentence was at 15 years," she said of the government's request. "I think the court is going to be looking on the low end of 2-3 years and, I think, on the high end, somewhere between 7, 8, 9 years. Under 10, would just be my guess."
Ahead of the sentencing, Holmes' lawyers gave the judge 130 letters in support of Holmes, including one from New Jersey Senator Cory Booker. He said the two became friends years ago when they met at a party and bonded over being vegan.
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Sen. Booker said he was writing to advocate for a "fair and just" sentence for Holmes. "As author Bryan Stephenson has said, each of us is more than the worst thing we've done. I firmly believe in the possibility of rehabilitation and in the power of redemption for anyone.," Booker said. "And I believe that Ms. Holmes has within her a sincere desire to help others, to be of meaningful service, and possesses the capacity to redeem herself."
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Holmes' partner, hotel heir Billy Evans, also sent a lengthy letter that included personal photos of Holmes with their dog and young son. Another letter from a friend confirmed Holmes is pregnant again.
Kreitzberg said neither the letters -- or her pregnancy -- are unlikely to make a huge difference in sentencing.
"Given her background, her privilege, her socioeconomic status, and quality of her lawyers," Kreitzberg said, "It's not surprising that they've collected that number of letters."
"I think the judge has to see them because if they didn't show up he'd wonder why not," she continued, "But those will really be a small effect on the sentencing partly because the guidelines give very small measure to personal, individual characteristics."
Still, given the intense public interest in this case, including ABC News' "The Dropout" podcast and the Hulu drama series, Holmes' attorneys are arguing she has already paid a price for her crimes. "Ms. Holmes is punished every day for the offense conduct, has been for years, and will be for the rest of her life," her attorneys wrote in court documents. But Kreitzberg says that's also not an argument that's likely to sway a judge.
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"If the court used that as punishment enough, then we're starting to enter the world of real privilege," she said, "That if you are a very public person you can say I don't need to go to prison because I've been publicly humiliated, and I don't think the court can afford to do that."
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The government also submitted victim impact statements from people who say they were negatively impacted by Holmes' crimes. According to reporter John Carreyrou, who first broke the Theranos story in the Wall Street Journal in 2015, one of those letters is from Holmes' own aunt who told the court she invested in Theranos and believes her niece should serve time.
Kreitzberg said working in Holmes' favor is that she has no prior criminal history. Working against her is the sheer amount of money she defrauded from investors.
She said something that could impact her sentencing is her relationship with former Theranos COO Sunny Balwani. Holmes had alleged there was emotional abuse in that relationship.
"Hiding in the background is this issue that got raised in motions, but not as much in trial, and that is the intimate partner abuse issue," Kreitzber said.
"According to the defense, she was influenced, impacted, even abused by this older, more sophisticated man."
Kreitzberg said it's unclear to what extent that could impact Judge Davila's decision to make the sentence slightly lower. But ultimately, she believes Holmes will serve prison time, in part, to send a message.
"They're going to have to look at what message, a general deterrence, it's called. What message to other companies, other investors," she explained. "They're looking at what are the consequences going to be, and so I think there has to be incarceration."
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