Elizabeth Holmes has filed 3 requests for a new trial in 2 days as she awaits sentencing. Legal experts say it's unlikely she'll get a do-over.

• Theranos founder Elizabeth Holmes has filed three requests for a new trial in the span of two days.
• Convicted of fraud and conspiracy in January, Holmes is set to be sentenced in October and could get decades in prison.

With the possibility of decades in prison looming over her head, Elizabeth Holmes is making every effort to get a second chance in court.

The Theranos founder, convicted on four fraud-related charges in January, made three requests for a new trial in the span of two days last week.

Prior to filing the three motions, Holmes had asked the judge in her case to throw out her conviction on the grounds of "insufficient evidence." He tentatively denied her request earlier this month. Holmes' sentencing hearing is set for October 17.

Complimentary Tech Event

Transform talent with learning that works

Capability development is critical for businesses who want to push the envelope of innovation.Discover how business leaders are strategizing around building talent capabilities and empowering employee transformation.Know More

For all her efforts, Holmes' odds of getting a new trial don't look good, two legal experts told Insider.

"These are all Hail Marys," said Jason Ross, a partner at law firm Dykema whose areas of focus include white-collar criminal defense. "I don't think any of these are going to ultimately get her a new trial."

The first request

Last Tuesday, Holmes' team filed a motion asking for a new trial after one of the prosecution's star witnesses, former Theranos lab director Adam Rosendorff, allegedly went to her house in August and expressed regret over his testimony, saying the prosecution made things look worse than they really were.

Rosendorff's remorse doesn't necessarily cast doubt on the veracity of his testimony, according to Amanda Kramer, a partner at law firm Covington whose specialties include white-collar criminal defense.

"It's not uncommon for witnesses who had a personal connection with the defendant to feel bad about being a witness at trial against the person," Kramer told Insider. "The fact that he feels badly about the role that he played in the trial doesn't mean that any of his testimony was false or inaccurate or misleading ... You can feel bad about the role you played at trial and still have given perfectly truthful testimony."

During the trial, the defense also spent a considerable amount of time cross-examining Rosendorff, which doesn't help its case for a do-over now, Ross said.

"I think you're going to hear the government say this is an adversarial system, this witness was subject to rigorous cross-examination, and if there were a different way to portray things or a different side of that, then Ms. Holmes' attorneys certainly had the ability — and to some extent actually succeeded — in bringing that out on cross," Ross said.

Then there's Holmes' mixed verdict: She was convicted on four counts and acquitted on four others, and the jury deadlocked on three more.

"The fact that they acquitted on some demonstrates that they carefully parsed through what [Rosendorff] said and weighed all of the evidence together and didn't just accept all of his testimony," Kramer said. "That would make it much harder to get a new trial on the basis of him expressing regret in these circumstances because it would undermine the defense argument that he was the linchpin witness for all of the counts."

The new requests

A day after filing that motion, Holmes made two more requests for a new trial. In one, her team took issue with the prosecution's different portrayals of Holmes' relationship with Ramesh "Sunny" Balwani, her ex-boyfriend and former right-hand man at Theranos, in their two separate trials.

The motion says the government played up the differences in age and experience between them in Balwani's trial, to make the case he had a big role in what went wrong at Theranos. But in Holmes' trial — where the defense says highlighting these differences might have led to Holmes being acquitted on more charges — the government played their cards very differently, according to Holmes' attorneys.

As for this second request, there's not a lot of case law that would indicate the prosecution has to stick with one interpretation of evidence across separate trials, Ross says.

"If the government's arguments are consistent with the evidence admitted in that trial, then the fact that there's a different argument made based on different evidence is not a strong basis for relief or for getting a new trial," added Kramer.

In the third motion, Holmes says she was denied emails that showed prosecutors failed to take appropriate steps to preserve a Theranos database of testing and quality control data that she claims would've helped her during her trial. The government produced these documents for Balwani's trial though, Holmes pointed out.

"Without being able to prove that the database reasonably could be expected to result in an acquittal, the defense would have to show prosecutorial misconduct, and it would have to be of such degree that it doesn't seem was present here," said Kramer.

The judge will hear from both sides regarding the three motions on October 3.