Boies was first approached to be general counsel of the startup in 2011. His first case for the company was a patent case that settled in 2014, for which the firm was paid in more than 300,000 shares valued at $4.5 million based on a valuation of $15 a share at the time, according to The Wall Street Journal. He joined the company's board of directors a little over a year later, in 2015.

In October 2015, Wall Street Journal reporter John Carreyrou reported the first in a series of articles that outlined problems and fraud within Theranos, namely that the technology central to its mission could not "quickly process the full range of laboratory tests from a few drops of blood," as Holmes had promised.

In November 2016, Boies cut legal ties with the company over a disagreement in how to handle the government investigation and resigned from the board in February 2017. In June 2018, Holmes and Ramesh "Sunny" Balwani, Theranos' president and chief operating officer, were indicted. Holmes now faces 12 counts of fraud, carrying a maximum penalty of 20 years in prison and a fine of $250,000 for each count.

While some legal observers saw an inherent conflict in Boies' representation of shareholders, as a director, and the company, as its attorney, many hold the view that Boies did nothing wrong in accepting his dual roles.

But the legal angle is only one part of the equation, image is another.

A former partner at the firm said that while they believe Boies did nothing wrong in representing Holmes and being paid in stock, his representation and the fallout did hurt the firm's image in the eyes of many clients.

"His connection with the company during the difficult times could have been a problem, particularly during his time where he held a dual role," said Ross Fishman, a legal marketing and public relations specialist, in an email. "That's a tricky position, particularly where an individual's reputation is so closely tied to the firm's. It's a risk. The upside of maintaining that public relationship is pretty low but the potential downside is significant, so most firms would immediately distance themselves from the whole situation."

But, Fishman added, "there are a handful of lawyers whose brands as renegades can withstand more pressure than others, and David Boies holds that position."

According to three former partners and sources close to the firm, Boies' representation of Theranos was a contributing factor in the departure of several of the firm's partners last year—especially those who resided on the West Coast where clients, they said, are much more sensitive to these issues. Boies' relationship as a friend and long-time attorney to disgraced filmmaker and convicted sex offender Harvey Weinstein was also a strain on the firm's image, they noted.

"It's an uphill thing everybody is battling," one former Boies Schiller partner said. "People don't want to go out on a limb with their boards to bring on the attorneys who represented Weinstein and Theranos."

At least 28 Boies Schiller lawyers have left the firm's Los Angeles and San Francisco offices since the beginning of 2020, including more than a dozen partners who left to King & Spalding in April of last year. In that time, that office also saw the arrest of Boies Schiller partner Joshua Schiller, who was charged in January for misdemeanor domestic violence after an incident involving his wife in his Ross, California, home. The charge was later dropped in April.

When it comes to the trial itself, it is yet to be seen how Boies and his firm will be involved.

In July, U.S. Magistrate Judge Nathanael Cousins of the Northern District of California ruled that emails between Boies and Holmes did not fall under attorney-client privilege, as Holmes' defense lawyers at William & Connolly have argued, a ruling that could potentially mean the public unveiling of at least 13 emails listed on the government's exhibit list.

And Boies Schiller partner Heather King may be called as a witness, according to an Aug. 20 court filing. King was general counsel of Theranos before rejoining Boies Schiller in 2016.

Others who were involved in representing the company have since left the firm, including former partner and Boies Schiller general counsel Michael Brille, who announced he was retiring in April, and former firm partner Amy Mauser, who joined Paul, Weiss, Rifkind, Wharton & Garrison in August last year.