‘Reggie’ Director Alex Stapleton Wants You To Know There’s Much More To Reggie Jackson Than Just His Prowess On The Ballfield

When you think of Reggie Jackson, you don’t just think of his three home runs in the penultimate game of the 1977 World Series. In fact, most baseball fans and casual observers would reference his combative personality, one that seemed to make for a perfect foil against managers, competitors, and team owners. Over the years since his retirement in 1987, the wider story of the Hall of Famer hasn’t changed all that much in the eyes of people who loved or loathed him for his bold talk and confidence.

It’s all the reason why the latest sports documentary from Prime Video, Reggie, breaks through in a completely different sports and media landscape versus his playing days. In the latest offering of visual reflections of athletes from yesteryear, a slightly weathered but still honest Jackson opens up about the highs and lows of his career along with how current affairs in America influenced his ongoing involvement with the game of baseball.

Decider spoke with Reggie‘s director Alex Stapleton about how the project came together, including a discussion on how the present-day social justice movements helped re-tell Jackson’s story of finding dignity and respect as a prominent Black athlete. 

DECIDER: Why were you chosen to be the director of this story?

ALEX STAPLETON: Well, that’s a good question that I would love to actually ask Reggie (laughs). You know, I have done a lot of sports projects, I was the showrunner on Shut Up and Dribble. When I got that project, it was called ‘The Draft,’ and it was just going to be a series for Showtime about the NBA draft class. And when I got into it, I saw that there’s so much more to this story, there’s a whole another level to flip the coin over to this off-the-court story about Black men navigating the American dream and the post-Jim Crow era America, and I really thought that it would be cool to kind of capture this brotherhood that all these guys shared. And, you know, that documentary came out and it was a success. And I think it was one of the first kind of like popular culture documentaries (I’ve done) that also had something more to examine and I had gone on to do some more sports projects. 

I met with Reggie and Delirio Films; the production company that brought me in to sit down with him. I think he really wanted Spike Lee to direct his documentary, and I’m definitely not Spike (laughs), but our conversation was just really interesting. What was immediately attractive to me as a filmmaker about Reggie’s story is that there’s so much more substance, he’s so much more than an athlete. I mean, all pro athletes are, but his story spanned over so many decades and through a very tumultuous time in this country. There was an openness there that I think we also really bonded over. And so, I think it was just an odd pairing, initially. I’m not a New Yorker, I’m from the South. I’m a Black woman, but in the sports space, and I think he was up for the challenge.

Photo: MLB via Getty Images

The majority of Reggie is filmed at the onset of the coronavirus pandemic, with the social tumults of 2020 also top of mind for most Americans. Beyond production restrictions of the time, how did that period influence your directorial hand?  

Yeah, it’s not my style to do like a ‘cradle to now’ kind of story. I think that that’s a little bit of outmoded storytelling, I think audiences want to be challenged with something a little bit different. Something else that I got really excited about is that Reggie is still very active and works. So he had this very active timeline that was going on. And when we met, we kind of like shook hands, we’re going to do this film, yet there wasn’t really a roadmap of how we were going to do it yet. But then 2020 happened and the whole country witnessed the murders of George Floyd, Breonna Taylor, and Ahmaud Arbery. Reggie and I started talking and he just very upset. And then we just started having these really long phone conversations. And I think what was happening for him was that he was reflecting on his whole life. I think there was this kind of moment where he was asking himself “What is my legacy going to be?” But more importantly, “What can I bring to the game now? What can I do that because I’m still actively a part of MLB? What can I do to like really create change?” All of these questions started to bubble up. 

And so we immediately started filming by going into a studio. It was so COVID as well. We had all these like limitations of how we could shoot. And through that process, he started to realize that he was going to make some changes; he was ready to leave the New York Yankees and wanted to go out into the world and go talk to the people about what was happening in real life. He was actually speaking to his friends – Derek Jeter, Julius Erving, Hank Aaron, all these guys are people that he actually has (had) a real friendship, and he values their opinions. And I think he was kind of testing out, like, what should I do? He was ideating what was the next chapter going to be. And then he was like, “Do you want to come along for the ride?” I was like, “Yes, I will be there!” So we went on this kind of like mini tour and just started talking to people. He had real life things that were very current that he wanted to talk about. And then we decided to use the opportunity to also kind of talk about back in the day and all of that just started to kind of come together. And it was great because then I was able to edit to create a story that feels very present day, very active, with pieces of his life intermittent throughout. 

Most people – certainly a lot of non-Black people – might be very surprised to hear some of the stuff he discusses. Do you think that this would have been a completely different documentary if it was made before 2020? That he may have not been as forthright on the impact of race during his playing days and beyond? 

I don’t think so. Reggie has always been like an open book. Even when I looked at the archive, I’m like, “Oh, my gosh, he hasn’t really changed.” I think that people have registered (the race discussion in sports) differently through the decades. Back in the ’70s, he was saying the same stuff about people were questioning his salary when he was the highest paid player in baseball. And even he said “you’re only asking me that because I’m a Black man with making this kind of money.” He was so ahead of the time, being very vocal, especially compared to other Black superstars of that era. But he also wasn’t what we what people thought of as an activist. He wasn’t Kareem (Abdul-Jabbar), he wasn’t out there marching in the streets, necessarily, in that time period. And I think that people, especially the media, didn’t really understand what to do with (Black superstars). And I think that all the attention just went towards them believing, ‘oh, he’s just difficult.’ You get all their negative connotations of a grown Black man being honest and speaking his mind.

Now the media is so different, and so many athletes have been able to navigate their own platform, that they don’t really need the media to interpret things for them. Back in the day, the (sports) media was all white men and the way that their stories came out were totally different. So I feel like Reggie has always been the same. And I think with the film, maybe where he was in his life as far as like leaving the Yankees and going to the Houston Astros, maybe that wasn’t (originally) going to be a part of it. 

Photo: Getty Images

His years in the East Bay are fascinating – it seemed as if he loved Oakland and playing for the A’s, but friction with team owner Charlie Finley over his salary may have soured him on his time there. (Jackson returned to the A’s for his final season in 1987.) Was talking about Oakland difficult for him because of the trajectory his life would take upon his eventual free agency? Does he still have an affinity for The Town?

Yeah, he’s California-based, and I think that will always be his home. I think Oakland was really the birth of him starting to understand – at a really young age – that there was going to be life after baseball. He had this crazy relationship with (A’s owner) Charlie Finley, and maybe a little bit of a love-hate relationship with (Yankees owner) George Steinbrenner in New York. I think part of the reason why there was a little bit of friction was because Reggie was studying like the owners, trying to understand like the mechanics, the economics, the front office part of baseball. I remember reading when he was in Oakland, and in his late 20s, he talked about ownership. Back then, there’s no black coaches in baseball, there’s no black people in the front office. He said, “I’m not trying to be a manager, I want to own a team.” And the third part of the film gets into his quest for ownership, and how he was shot down twice despite being the highest bidder. And I think that every time there was some crazy thing that happened to him and his career, Oakland and Northern California, is always the place where he goes back to reset, recalibrate, so this is a really special place geographically for him.

The New York story feels well-worn, but it’s how most baseball fans outside of Oakland identify him. (After being traded from Oakland to Baltimore in 1976 because Finley’s refusal to pay him more money, Jackson signs with the Yankees as a free agent.) His first season in pinstripes is the stuff of legend, for better or worse, as he’s at the heart of the team’s “Bronx Zoo” era. What new or at least different spin were you aiming for to reflect on this part of his legacy? 

I think the ’70s and ’80s, especially in New York, is a fascinating era of Black history and it’s the continuation of the civil rights movement, but in a more nuanced, different type of way. Black folks at that time, as a community, were not this monolithic group. There’s now different classes and different classes existing within integrated worlds. In Reggie, I find a lot of fascination with that. I also think the personal is political, and I think just his mere existence and what he was doing professionally, and what he was demanding, was very political. 

(New York) always turns into “Reggie Jackson versus Billy Martin,” and that’s always what everyone wants to talk about. But the bigger story is how (their relationship) is just a symptom of this young Black man demanding respect, being financially independent, and demanding respect in a very white space. While there were successful Black people before, I think a lot of the success we had, culturally, was within our own communities. And I think that’s what’s so fascinating to me about Black athletes of the ’70s. I mean, look at Dr. J (Julius Erving) – he and Reggie were trailblazing in a very different way that I think a lot of people don’t talk about when we talk about civil rights. When we talk about ’the movement,’ it’s just Jackie Robinson and the conversation kind of ends with like Martin Luther King Jr. and Malcolm X, right? 

Reggie’s story, to me, is a part of the movement, but it’s different. Because once again, it’s like the old adage: do you sit at the table or do you flip the table over? Reggie was trying to navigate the space that ballplayers weren’t in. Henry Aaron even said it to Reggie – “you were never afraid, and that was something that was admirable to us, you spoke your mind.” And that was a very political thing to do. You know, like he was risking a lot by doing that. Of course, we had to talk about what happened between him and Billy, but I hope that in the film, you can understand this bigger thing that was going on at the time, and because I do think that that era kind of gets jumped over and not discussed.

Growing up with a father who once played in the Negro Leagues certainly shaped Jackson’s mindset when he made to the majors. However, you didn’t get into his upbringing until maybe about two thirds of the way through where we see him talking to his brother and sister. In veering away from the traditional format of reflecting on someone’s life, what were you hoping the viewers understand about Jackson? 

With storytelling, I want the audience to earn that backstory when we get to a certain point of history, so that it hits differently. If you just did a timeline of who he was growing up in Pennsylvania and who his father was, I don’t know if it would necessarily hit you as hard. When you’re later learning about who his father was playing for the Negro Leagues, being a businessman and helping Reggie through one of the hardest chapters of his professional career, it’s like unlocking more of him. You’re unlocking more about what makes Reggie tick. Now, look, if I was making a doc series, it might be different. I don’t think I would wait. Like, if I was making for, you know, a four-part series, I wouldn’t necessarily wait until the third hour to get to that. 

We wanted you to go on a ride with the story, and we wanted it to be interesting, entertaining; you get the good, bad and the ugly. But I think that just kind of somatically learning about Reggie’s life versus a typical timeline was very interesting to us. And he has so much there’s so much more than some even in the film. I think (a series) would be almost kind of like a Forrest Gump story. This man was everywhere for decades, in the middle of crazy social change. 

"Reggie" Special Press Screening And Q&A
Julius Erving, Alex Stapleton, Reggie Jackson, and Head of Original Content, Amazon Sports, Matt Newman attends the special press screening and Q&A of “Reggie” at Crosby Street Hotel on March 21, 2023 in New York City.
Photo: Getty Images for Prime Video

With so much left on the cutting room floor, what would you have included in the film if you have another five or ten minutes in runtime?

I would have wanted to get deeper into the ownership conversation – and we talked about it – but I think there was a lot there. Like, even though he was insanely successful in his field, he was still fighting to get to like the next level. And to me, there was a message that I wanted to dig deeper in, because I think that those also are very inspiring stories that hit people in a different way, where you have so many people from marginalized backgrounds that have great jobs, are doing amazing things, but where are the tools? Like, how do I learn more to navigate those spaces?

That’s what comes to mind immediately, but there’s so much more of his professional career. He goes to Anaheim, and we didn’t get to talk about that period, really, at all. And that was a big bummer to me. And then there’s a Reggie of today, but beyond the Astros, he’s deeply, deeply rooted in giving back to the community with STEM. He has an organization where he works with STEM, getting interested in kids into STEM education programs and he’s just doing so much right now. And you know, once again, they didn’t have the room to get in there. And I would say what I really wish that we had more time to do was the car collection, which is insane. 

How did he feel about the finished product?

I remember the first time I showed it to him – of course it’s the part that I hate when you show it to the subject and you’re like sweating, a nervous wreck. And we screened it, and it was him in a couple of his really close friends. I was just I was so nervous. And afterwards, the lights came up and it gave me a hug. “Thank you, Jesus.”

He wanted some stuff that that’s not necessarily in there because there’s just not the real estate, there’s not that much time to go over a life as great as his. I think he was I think it was surprised. I think he was like, “okay, I didn’t get Spike Lee, but Alex Stapleton did an okay job (laughs).”

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.

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