Chicago’s own Montana of 300 is in legal trouble again. The rapper, whose real name is Walter Anthony Bradford, was arrested on February 11, 2025, on multiple charges, including criminal trespassing, domestic battery, resisting arrest, and theft.
Raised on Chicago’s South Side, he turned to rap as both a sanctuary and a vehicle, crafting intricate, metaphor-filled bars that immediately set him apart from the pack. He started the rap collective “300” in 2008 alongside Montelle Talley, named after the 300 movie’s warrior ethos. He gained traction 2014 with Cursed with a Blessing, a mixtape that solidified his reputation as a lyrical force to be reckoned with.
His 2016 independent debut, Fire in the Church, was a testament to his grind, charting at No. 95 on the Billboard 200 with no major-label backing. More than a rapper, Montana had become an emblem of self-sufficiency, releasing new music on May 20 of every year—a date that’s taken on almost mythic importance among his fanbase.
Montana’s latest arrest is not his first run-in with the law. In 2017, he was jailed on gun charges and obstruction of justice. But in typical Montana fashion, he seized the moment and turned it into fuel—dropping Don’t Doubt the God while in jail and proving that not even prison could silence him.
With this new legal challenge in his path, fans can’t help but wonder: Will this recent setback slow down his momentum, or is it just another page in his relentless pursuit of greatness? If the past has shown us anything, Montana of 300 doesn’t fold under pressure—he thrives in it.
As news of his arrest spread, people were split. Some of his fans were disappointed, hoping he’d shed the excess of his legal troubles and just release music. Others stood firm, praising his tenacity and calling for his immediate release. It’s a hip-hop story as old as the time when personal demons were part of an artist’s mythology. And if anyone can turn adversity into angry rhymes, it’s Montana of 300.
Although he previously said 2022’s Rap God would be his last solo LP, Montana has a tendency to go against expectations. With his track record of planning ahead—pre-recording music and videos to maintain a steady output—it’s conceivable he has something else in the works, despite what he’s going through right now.
