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Esquire First Look:<i><em> The Greatest</em></i> Goes Beyond the Ring to Show Muhammad Ali’s Family

Esquire First Look:<i><em> The Greatest</em></i> Goes Beyond the Ring to Show Muhammad Ali’s Family

esquire.com 14.10.2026 16:00 6 views
You’ve watched documentaries and seen the photographs. A new Prime Video series will reveal even more about the sports icon.

The certified Greatest of All Time has had umpteen books, documentaries, and biographical dramas that tell and retell his years as a heavyweight champion and a political activist. Hell, there is a movie about Muhammad Ali, starring Muhammad Ali. (Not to mention an iconic Esquire cover featuring the legend.) But a new Prime Video series, simply titled The Greatest, aims to be more than another boxing biography. The Greatest isn’t just about the man who was born Cassius Clay, but the family who raised him into a legend.

It’s a granular deep dive into Muhammad’s life, to understand who he was, how he started, and how he progressed to become one of the most beloved icons.” Created by Ben Watkins, with Lonnie Ali among its executive producers, The Greatest stars newcomer Jaalen Best as Muhammad Ali in the years spanning his gold-medal victory at the 1960 Olympics in Rome to his championship bout against Sonny Liston in February 1964. Between these hard-fought wins, Ali lives in Louisville—where his godlike status collides with Jim Crow—and trains to turn pro with the support and tough love of his family: father Cassius Clay Sr. (Omari Hardwick), mother Odessa “Bird” Clay (Dana Gourrier), and brother Rudy, later Rahaman Ali (Kai Parham). The series will begin streaming on Prime Video on November 4.

You can watch the trailer below, along with exclusive images only at Esquire. In conversations with Esquire, Watkins and the stars describe the series as a coming-of-age family drama that so happens to follow the footsteps of an icon. That meant putting an equally big spotlight on the people who surrounded Ali in his most formative years—and being truthful to who they were.

That means you’re going to see parts of Muhammad Ali that aren’t always flattering. We shouldn’t do something where he’s perfect.” At the same time, Watkins and his team knew they were treading familiar ground. Throw a rock at your Roku and you’ll hit a documentary about Ali.

And his mythical boxing matches? They’re on YouTube, upscaled to 4K. So Watkins, whose previous work in television includes Burn Notice and Cross, imposed a rule (albeit loosely) for his writers’ room.

He admits it’s an exaggerated rule—so much of Ali’s legend unfolded in the public eye—but it was about setting “intention.” “We need to be excavating, looking for details that give us a better understanding of who this is. The Crown is a recent example, where some of the best episodes are about things no one ever knew about. That’s what I wanted to do.” Which is what made Ali’s family compelling subjects for a streaming series.

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