Stream It Or Skip It: ‘Reggie’ on Prime Video, A Bold and Reflective Look at the Legend of “Mr. October” 

No sport is more steeped in yesteryear than baseball, but with Reggie from Prime Video, this reflection of a legend says a lot about where the game and American society are today. There may never be another like Reginald Martinez Jackson, better known to baseball fans as “Mr. October” for his excellence in the World Series. In this 104-minute documentary by Alex Stapleton, his words and actions have aged far better than anyone could have anticipated thanks to the advancement of player empowerment and our understanding of what prominent Black athletes endured for generations.

REGGIE: STREAM IT OR SKIP IT?

The Gist: The documentary is about the Baseball Hall of Fame outfielder Reggie Jackson, who was known as much for his candid talk as his prodigious skills on the baseball field. Jackson was a brilliant player whose anger appeared to overshadow his talents and cohesiveness with most teammates. The anger wasn’t sprung from nowhere as his response to racism, an uncanny media savvy, and the contentious introduction of free agency to Major League Baseball defined much of his career.

Despite his individual and team success with the Oakland A’s (league MVP, multiple All-Star appearances and three of his five World Series championships), Jackson continually clashed with team owner Charlie Finley because the businessman was adamantly against free agency. After a 1976 trade to Baltimore because of his demands, Jackson finally gets the payday he’s been looking for a year later thanks to George Steinbrenner and the New York Yankees. The film looks back at a rocky first season in pinstripes, including Jackson’s infamously combative relationship with manager Billy Martin, a sarcastic quote that birthed his “Mr. October” moniker, and the fan bases’ eventual acceptance of Jackson thanks to his brilliance in the 1977 World Series.

Jackson is not the only iconic athlete featured in Reggie. The social justice conversations that took place in 2020 inspired him to reflect on his own life and how he chooses to use his experience to help the next generation of baseball players. He visits close confidants – Julius Erving, Henry ‘Hank’ Aaron, and Derek Jeter, among others – that are advising him on his next steps as he considers leaving a longtime advisory role with the New York Yankees. Along the way, he has unique conversations with each of them about the depths and valleys of his career.

What Movies Will It Remind You Of?: Reggie may be a baseball documentary, but the active narrative arc – connecting with Jackson’s contemporaries to talk about his past while he was trying to sort out the present – were reminiscent of Willie, a documentary that followed the campaign to induct the NHL’s first Black player, Willie O’Ree, into the Hockey Hall of Fame. (In February 2020, Decider spoke with its director Laurence Mathieu-Leger about her approach to telling that story.)

Performance Worth Watching: Jackson himself, which is and isn’t a surprise. He remains as alluring as an elder statesman as he was in his younger days. Jackson still has a frankness about him, as he’s direct and open about what’s on his mind. However, the infamous temperament of his athletic prime turned to an aged wisdom as Jackson now has the added context of the history he helped write behind him.  

A question that director Alex Stapleton asked him rings loudly throughout – “Are you in search of your own legacy?” – and we get to watch Jackson reconcile his role in baseball history in real time.

Memorable Dialogue: At one point, the film dives into the contentious relationship between Jackson and Yankees manager Billy Martin. Jackson talked about how he disliked seeing himself in video because of how pained and terse he appeared, as if the weight of the world was on his shoulders. Compared to his peers Bob Gibson, Frank Robinson, and Henry ‘Hank’ Aaron, he observed that they had similar expressions because they were looking for dignity. 

That observation led to a stirring conversation he had with Aaron about Martin. (Aaron passed away in January 2021, not long after the documentary’s filming.) The former home run king and ambassador of the game said “you know, Reggie, I admired you because of the fact that you let people know where you stand. You didn’t have to bite your tongue to say it.”

To this day, sports media personalities tend to compare the demeanors of popular athletes (especially Black ones) with certain coaches to make a grandiose statement about a team’s performance. Considering the somewhat stoic nature that Aaron embodied as a player and his well-chronicled admiration for a similarly tempered Jackie Robinson, it was rather powerful to hear him validate the brashness Jackson brought to the game, to the Yankees and Black athletes in general. 

Sex and Skin: None. 

Our Take: At the onset of the film, Jackson said “I have hesitation with this documentary because I don’t have control of it.” It was a fascinating quote for multiple reasons – chief among them is that he’s always had control (and confidence) on what he said, but none over how people felt about him. 

There’s a brilliance in how he and Stapleton decided to tell his story – allowing Jackson to become both the interviewee and interviewer. Much of that is a credit to Stapleton, who could have easily asked historians, sportswriters, and a handful of Jackson’s closest friends to interpret his life’s story with or without him. Stapleton, who also helmed Shut Up and Dribble for Showtime, deftly balances archival footage of Jackson’s career with his in-person conversations and her one-on-one interviews to show that his story is not dissimilar to those of current era legends such as LeBron James, Lewis Hamilton, or Serena Williams.

Our Call: STREAM IT! If you walked into your nearest Barnes and Noble or flipped to the archives of a major sports channel, you’d have a hard time avoiding the Yankee lore (or propaganda) – it’s inescapable, no matter where you live. Just about every piece of Yankee-related baseball media is based on Babe Ruth, Joe DiMaggio, Mickey Mantle and the late 1990s ‘Core Four’ era of Derek Jeter, Andy Pettitte, Jorge Posada, and Mariano Rivera. All of it is centered around the franchise’s manifest destiny of winning with a so-called style and class, even if the reality was far different.

Jackson’s story doesn’t fit neatly with the rest of the Yankees hagiography, starting with the fact that he was a star before coming to New York. While Jeter is the franchise’s best-known Black (and biracial) superstar player, Jackson was the first Black superstar player on the Yankees who was unabashed about his racial identity and his talents. Contending with the larger-than-life personalities of white team owners and the ‘my way or the highway’ egotism of Martin, he became the archetype of New York’s most self-indulgent cliché: the athlete who had a hard time dealing with the bright lights of the big stage. (This writer can say that as a born and raised NYC native.)

Thankfully, Reggie gives the viewer a fuller picture of how he both defined and contradicted that convention. 

Jason Clinkscales is the founder and editor-in-chief of The Whole Game, and his work has been featured at Awful Announcing, The Week and Dime Magazine. A New York City native, he is also a former media research analyst in both television networks and advertising agencies.