Alex Spiro, Elon Musk's personal attorney, is a free speech advocate for hip-hop

Elon Musk's takeover of Twitter late last month as CEO has ignited a public conversation about whether the billionaire will obstruct or encourage free speech on the social media platform, which has about 240 million active users worldwide.

An early sign of Musk's direction may be evident by his inner circle, the center of which stands Alex Spiro, his personal attorney. Known as a powerhouse attorney representing world-renowned celebrities and athletes, Spiro is also a staunch free speech advocate, particularly in cases that intersect hip-hop music and criminal justice reform.

Concerns over the future of free speech on Twitter have come largely from Musk’s own posts since he took control of the company. Although he has said that existing laws protect Twitter from hate speech, he has said Twitter cannot be “considered inclusive or fair if it is biased against half the country,” which has made some worry that leniency toward extreme voices may be in the platform's future.

A flood of fake accounts impersonating public figures and brands overtook the platform last week after the launch of paid verification badges, raising fears about the supercharged spread of misinformation. Musk himself posted a link to a story about a baseless conspiracy theory about the recent attack on Paul Pelosi, the husband of House Speaker Nancy Pelosi. Musk later took the tweet down. Musk has also said that accounts impersonating others will not be tolerated unless they clearly state they are parody accounts.

Spiro declined to discuss Musk or Twitter for this story, but he did tell ABC News that free speech "is a core, fundamental belief" of Spiro's that has guided his career, which started when he was a prosecutor in Manhattan with the New York County District Attorney's Office.

"I'm hoping that free speech in music is something we could all get behind," he told ABC News.

A "mirror" of Musk

Spiro met Musk in 2019 when representing him in a defamation lawsuit by British cave diver Vernon Unsworth, in which the Tesla CEO had called Unsworth a "pedo guy." Spiro won that case on Musk's behalf, arguing that Musk was ultimately trying to fund efforts to save a group of Thai teenagers who were trapped in a cave and saying the comment was a "throwaway insult" after Unsworth tried unsuccessfully to characterize him as a "billionaire bully."

"The First Amendment does not [just] protect compliments and happy speak, it protects unfavorable speech. It protects all speech," Spiro said in a recent Original Jurisdiction podcast interview. "If we start policing speech, where are we? We're in a bad place in our society and in our world."

After that, Spiro continued to represent Musk in various legal battles, including continuous investigations by the U.S. Securities and Exchange Commission, one involving Musk's appeal to a $40 million SEC settlement for alleged securities fraud. Bill Burck, a co-managing partner of Quinn Emanuel Urquhart & Sullivan, who helped recruit Spiro to the firm in 2016, said Musk required an attorney who was also a personal confidante.

Musk "clearly thinks outside of the box and he follows the beat of his own drum, and he looks for intellectual courage and extreme dedication," Burck told ABC News. "Alex mirrors that. He is probably one of the very few people who can keep up with the ideas and not be hamstrung or straightjacketed by the perceived wisdom. That's probably the larger reason why he has clearly gotten Musk's trust in a way that very few other lawyers have."

Even in his early days, fresh out of Harvard Law School and working as a prosecutor in New York, Spiro demonstrated the strength required "to tell clients the truth," said attorney Elliot Felig, who worked with Spiro in 2009 when both were prosecutors at the Manhattan District Attorney's Office.

"Alex is the most confident courtroom attorney I've ever seen. Beyond that, he had a thirst for trying cases that was unparalleled," he told ABC News. "I think Elon Musk has a fearlessness and I suspect Alex is a good match."

Spiro, 39, was born in New York City but grew up in Boston. Early in his career, he worked at Harvard's McLean Hospital where he helped run a program for children with autism and Asperger's syndrome until he realized he could do more for their plight through the justice system. "I went to law school sort of by accident," he told the Original Jurisdiction podcast audience.

His interest in psychology served him well early in his life when it became clear he could relate to not just clients, but jurors from all walks of life, Felig said.

"The best prosecutors love being on trial and Alex loved being on trial. He wanted trials. He would go door to door looking for trials," he said. "The desire he had was innate. You can't teach it. It's a competitive spirit that some professional athletes have. They love the competition."

Working to decriminalize rap lyrics

Along the way, Spiro became a serious advocate for hip-hop artists who he believed were unfairly having their music and lyrics weaponized against them in court by criminal prosecutors. He told ABC News his interest in overturning wrongful convictions originated from observing prosecutors using the YouTube rap videos of defendants to characterize them as dangerous in order to have a judge deny their bail. The trend, he said, struck him as "particularly problematic and a hill to die on."

He ended up representing prominent hip-hop artists, including Jay-Z, 21 Savage, Meek Mill, Chance the Rapper and others, earning the title of "hip-hop's most sought-after criminal justice attorney" by Billboard. He defended Brooklyn rapper Bobby Shmurda, then on trial for gang conspiracy charges, in 2016, and remains the lead attorney for Jay-Z and his Roc Nation roster of artists -- a designation that required defending 21 Savage, who was arrested in 2019 for alleged immigration violations. (The case is still pending).

Along the way, Jay-Z enlisted Spiro to lead several criminal justice reform cases that had nothing to do with the music industry, such as filing a complaint in 2020 with the U.S. District Court in Greenville, Mississippi, on behalf of 29 inmates who authorities said were involved in a spate of violence that left five prisoners dead. Spiro argued that the deaths instead resulted from years of staff shortages and neglect in the state prison system.

Spiro also frequently partners with Erik Nielson, a liberal arts professor at the University of Richmond who has written extensively about hip-hop, to advocate for legislation to limit the use of rap lyrics used against defendants in criminal trials. Their work helped a law pass in California, and a similar bill is pending in both New York and New Jersey. Spiro co-wrote the bill and helped get stars such as Jay-Z, Killer Mike, Big Sean, and others to sign letters of support. A similar bill, the Restoring Artistic Protection Act, is working its way through the U.S. House of Representatives.

His advocacy originated in the case of Pittsburgh rapper Jamal Knox, who was found guilty in 2013 of threatening two police officers in his song, "F--- the Police." Nielson said there are hundreds of cases like Knox's, and he and Spiro -- who works pro bono on cases involving the legislation -- talk regularly about which potential cases could use their support.

"One thing about Alex is he really does walk the walk. He can achieve a lot in a very short period of time," Nielson told ABC News. "He's been an invaluable advocate of serious issues involving rap artists. He is driven and he is very effective, and so I can understand why someone like Elon Musk would rely on him."