Over his career he has represented multiple celebrity clients including Elon Musk, Jay-Z, MrBeast, Eric Adams, and Alec Baldwin.

[3][6] In 2016, Spiro filed a lawsuit against the University of Oregon on behalf of two basketball players who were expelled after being accused of sexually assaulting a freshman at an off-campus party in 2014.

[10] In 2017, Spiro won a lawsuit against New York City, which agreed to pay $4 million to Thabo Sefolosha, who was an NBA player for the Atlanta Hawks at the time.

[11][12] In 2018, Spiro was part of the defense team for David Demos, defending his case involving the use of illegal sales practices, including fraud for lying to clients.

In February 2019, Spiro was asked by Jay-Z and Roc Nation[13] to help with the immigration arrest of rapper/songwriter 21 Savage, resulting in the rapper's release from federal custody.

[15] In September 2019, Spiro obtained a dismissal of a breach of contract and unjust enrichment claim brought by a former trainer of tennis player Naomi Osaka.

[16] In December 2019, Spiro defended Elon Musk in a defamation case raised by Vernon Unsworth from statements made relating to their involvement in the Tham Luang cave rescue.

[19] In March 2020, Spiro and hip-hop artists Killer Mike, Meek Mill, Yo Gotti, and Chance the Rapper sent a brief to the United States Supreme Court, detailing the ways rap music is stigmatized and stereotyped by the legal system.

"[21] In May 2021, the family of Don Lewis hired Spiro to investigate his 1997 disappearance which gained renewed interest after the airing of the Netflix series Tiger King.

[22] In June 2021, Spiro obtained a temporary restraining order against Roc-A-Fella co-founder Damon Dash in Manhattan federal court, blocking a planned non-fungible token auction of his copyright interest in Jay-Z’s debut album Reasonable Doubt.

[26] Spiro has represented musical artists, such as Mick Jagger[1] and Bobby Shmurda,[2] as well as athletes, including Charles Oakley[27] and Julian Edelman.