High-profile defense attorney Drew Findling is taking his expertise in law and his understanding of societal prejudices from the world of hip-hop to the realm of politics after being retained by former U.S. President Donald Trump. Known for successfully defending multiple Atlanta rappers, Findling now faces a new challenge, defending Trump in two high-stakes criminal cases currently shaking the US political landscape.

Findling is no stranger to intricate cases and defendants embroiled in controversy. His formidable reputation within the legal fraternity was built brick by brick, starting as a public defender. Over the years, his firm, established in 1987, has defended some of the most high-profile personalities, from Shaquille O’Neal and Dennis Rodman to reality show stars and comedians like Katt Williams and Mike Epps.

But it was his success in representing rap artists that bestowed him with the nickname “Billion Dollar Lawyer,” an honor given by the late rapper, Young Dolph. Findling’s most notable triumph entails negotiating a plea deal for the hitmaker Gucci Mane, leading to the rapper’s early prison release and career resurgence.

Taking up Trump’s cases, Findling will primarily be tasked with articulating a free speech defense, similar to his previous cases where he fought assumptions that lyrics represented criminal intent. His approach with defending rap artists essentially involves challenging stereotypes and destructive narratives associated with the genre. As Findling has often pointed out, it’s misguided and prejudiced to pull a verse from a four-minute song and conjure up criminal charges. Now, he faces the unique challenge of arguing that the actions of a former President of the United States were simply a pursuit of constitutional guarantees.

Findling’s intriguing history is not without its tinges of irony. An outspoken critic of Trump, the lawyer has even previously donated to Fani Willis, the very woman now prosecuting the former President. Still, as all great legal warriors understand, cases are about the law and its interpretation, not personal feelings.

The move to represent Trump is certainly not a run-of-the-mill undertaking for Findling. Known for defending clients on the vulnerable side of societal prejudice, he will now be defending a man whose conduct has often been labelled as ‘un-American.’ This choice, Mr Findling equates with the mantra of the second U.S. president, John Adams, who defended British soldiers against murder charges during the anti-British sentiments post-Boston Massacre.

Regardless of how an observer may perceive the labyrinth of his career moves, Findling remains unapologetic about his personal and professional choices. He strongly holds that the choice of a client should not be based on their race, ethnicity, sexual orientation, political belief or gender. He has shown that time and again, whether representing rapper YFN Lucci, real name Rashawn Bennett while refusing a plea deal, or now defending Donald Trump against racketeering and other charges.

It’s not an easy task, but no one understands the game better than the “Billion Dollar Lawyer,” a man lauded as “the biggest lawyer in the game” by ex-clients. As Trump continues to circumvent legal advice and seek to delay the Georgia case, it’s clear that Findling has his hands full. But if history has taught us anything, it’s that Drew Findling is not one to back down from a challenge.