BRIN-JONATHAN BUTLER has experienced so much in his young life that I wasn’t sure where to begin with this interview. Many of his adventures are previewed in his captivating debut memoir, The Domino Diaries: My Decade Boxing with Olympic Champions and Chasing Hemingway’s Ghost in the Last Days of Castro’s Cuba. Between these covers are stories of Cuba with phantoms from history, athletes as homeland champions as well as disowned defectors, automobiles frozen in 1959, cultural meltdowns, and clandestine affairs. Butler unleashes a stirring portrait of Cuba during the decade he spent there in the waning days of the Castro era. He trained with champion boxers who chose to stay in Cuba rather than chase the lure of big US dollars, visited the original old man of Hemingway’s Old Man and the Sea, and even found time to have a fling with Castro’s granddaughter. All the while he wrote, observed, and filmed a way of life that may soon be, as Lawrence Ferlinghetti put it, a “gone world.”

Butler directed the documentary Split Decisions, which examines US-Cuban relations during the time of Castro. He is also the author of the ebook original A Cuban Boxer’s Journey: Guillermo Rigondeaux, from Castro’s Traitor to American Champion. His interviews with Mike Tyson and Errol Morris are available as e-interviews on Kindle, and his work has appeared in the NY Times, ESPN Magazine, Salon, Deadspin, Vice, and the Wall Street Journal.

We conversed online recently about the state of everything.

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DAVID BREITHAUPT: Norman Mailer described the intimidating effect of meeting Muhammad Ali in his book The Fight. He wrote: “Men look down. They are reminded again of their lack of worth.” What were you feeling when you walked into Mike Tyson’s mansion and interviewed him?

BRIN-JONATHAN BUTLER: Entering Mike Tyson’s front door through a cloud of marijuana easily was the most surreal moment of my life. Borges said, “The minotaur more than justifies the existence of the labyrinth.” In a way, that was how I viewed America’s obsession with Mike Tyson long before he meant anything to me personally. It was only after discovering he was as much a world-class victim as he was a world-class victimizer that his transformation resonated with me deeply. And until I’d discovered his story, I couldn’t find a way out of the torment and humiliation with my own childhood history of being bullied. Suddenly Tyson’s story suggested a millstone could be the most powerful weapon you could ever wield.

His first words as he approached me were nightmarish, “So how did this white motherfucker get inside my house?” Terrifying. Trigger-happy eyes glaring at me and everything. And you could see a whole pawnshop of broken dreams behind his eyes that tells the whole story.

But this man’s journey eventually saved my life, and I knew that he was someone who had never received much gratitude, from anyone, and that was all that was in my heart toward him. At first I felt like I’d brought a butter knife to a gunfight, but that gratitude was a very dangerous weapon to point at him, and we both realized it very quickly. We both knew you have to be crazier than Iron Mike Tyson to feel gratitude toward Iron Mike Tyson.

I was there to interview him, and at one point I asked him what he was always fighting for, back before it had anything to do with money. His answer: making his mother proud of him. She died before he ever saw her proud of a single thing he’d ever accomplished. Thirty minutes later he was cursing me out again for making him cry. Most extraordinary day of my life.

Your memoir begins with the thought that the real subject of every interview is that you can’t learn much about anyone from an interview. Were you surprised by what you encountered in Tyson’s mansion?

I think interviews are a bit like photography: what’s left out of the frame is often as important or even more so than what resides in the frame. All photographs are “staged” in that sense. As a rule, I think you learn far more about people from what they conceal than what they reveal. It’s not an exaggeration to say that Mike Tyson is one of the most exposed personalities in the history of the world. But I think the thing that surprised me the most from meeting Mike Tyson in person was how much we might not know about him and what makes him work. I had a hunch he was sexually abused as a child. It’s almost so obvious that it’s invisible. When Random House sent me an advance copy of his memoir, he had one line hinting at that experience and never returned to it. Nobody in the media went anywhere with it. When I interviewed him for the second time last November for Amazon’s Kindle Interview series, it turned out I was the first person to formally ask him about his own history with being sexually abused on the record and he confirmed it was true. While I was typing up the transcript of the interview, he went on the radio the next day, with the issue clearly still on his mind, and broke that story to the world.

What surprised me most about Mike Tyson is that he inhabits the role and identity of a Robert Ford as much as Jesse James all at once, predator and prey, overflowing with as much radical ambiguity as I think that dichotomy implies.

I came across a quote from James Gilligan (the author of Violence: Reflections on a National Epidemic) recently: “All violence,” he wrote, “is an attempt to replace shame with self-esteem.” Do you think this applies to the boxing trade in general?

It’s been my experience that hurt people hurt people. Boxers have always been the ultimate blue-collar worker: even when they win, they’re less than they were before they entered the ring. It’s an immutably sad and beautiful element of, to use Tyson’s term, “the hurt business.” Sure, there’s a masochism to boxers, but I think the primary motivation for that masochism is that all fighters are junkies for the truth of who they are. I don’t know of anything that exposes what a man stands for, is willing to stand up to, or just exposes the watermark of his soul quite like fighting. This is why most of us devote huge energies to avoid direct confrontation at all costs. We just want to get close enough that nobody holds us accountable for enjoying it. Fighters are the vainest athletes in existence, which means that they risk the deepest humiliation. There are exceptions, but the path to excellence in boxing is paved through grueling torment and humility. Compassion is a byproduct of that journey. Boxing gyms are lighthouses in their troubled communities historically, often the last lifeline for many who find them. The vast majority of fighters, the ones that I’ve met, learned to fight to feel safe in the world and protect themselves and who they care for. They’re a very sensitive group compared to most. It’s people who’ve never tested themselves the way fighters have that seek out violent conflict for its own sake. I think it’s those people who seek out violence to replace their shame and cowardice with self-esteem by going out on the attack. Boxing is about earning your self-respect for the rest of your life, and this is a sport that requires someone being in your corner, a surrogate, very likely, someone they never had before they entered boxing.

I couldn’t help wondering while reading your descriptions of Cuba that I’m looking at a world soon to be gone. You wrote that you were worried that Cuba was one dictator away from being like everywhere else. After the Castros are gone, what do you envision happening? Walmarts in pastel?

The funny thing there — the Cuba I experienced and wrote about in Domino Diaries, even the parting glimpses from 2011, is already long gone. For the first half of my travels to Havana, from 2000–2005, Castro speeches at the Plaza de la Revolución were yawned at by locals given how regularly they were obliged to attend them. After 2006, when he stepped down from power with a state secret illness, it was clear there would never be another after almost 50 years and God knows how many dead. Poof. Gone. That did change the complexion of Cuban society enormously, given the star power Castro had globally. At first, some Cubans prepared for another Bay of Pigs invasion. Most saw the absurdity of that. But the fatal invasion to Cuban culture, as they knew — it was indeed well on its way: tourism. America, en masse, is ready to take a big ol’ bite of the forbidden fruit they’ve waited for over half a century to taste. It’s a complicated, mixed blessing for nearly everyone involved.

What’s next is anyone’s guess. The same people have the same guns. The revolution, contrary to most media depictions, was never top-down, it was bottom-up. Many Cubans told me, we always had enough things we were afraid to lose, otherwise we would have toppled the regime ourselves. Which isn’t to say, by any stretch of the imagination, Cuba was ever a bed of roses. But cellphones have already infested the country, internet is being demanded, more freedom, economic opportunity … Cubans just want to determine their future on their terms. They don’t want to go back to being the Caribbean Las Vegas they were pre-Castro, and they don’t want to trade many things they have for what life is like in, say, Haiti or the Dominican Republic either. It’s not an accident Hemingway steered clear of Cuba in print. He covered every other war he lived through. Didn’t go near the revolution in his own backyard. I think the revolution remains how Castro initially described, “A revolution is a struggle to the death between the future and the past.” I’m not sure if it’s any different in our own country either, or anywhere else.

How much control do you think Cubans will have over their future? Are athletes becoming more able to consider making money in the US without leaving their families forever?

The last few years have seen more athletic defections than at any other point since the revolution began. The baseball signings alone have reached nine figures for a small handful of these top prospects.

From Cubans I’ve spoken with by email the last several months, hope remains very fleeting about prospects in Cuba, prospects for substantive change. I attended a Cuba conference at Columbia several months before Obama announced his major reforms and optimism was very present, but I haven’t seen that reflected from my contacts back on the island. On the contrary, there’s more urgency than ever to leave given the enduring frustration and glacial pace of many of the reforms.

Going back to the root of it all, you describe a brutal bullying incident, when you were young, in school. How did this change your life?

I became a virtual shut-in for almost three years after a swarming incident when I was 11. Apart from it being the worst day of my life, it happened in front of almost everyone I knew, and many of them joined in. I was pretty much paralyzed, unable to leave my front door without a debilitating sense of dread. I felt under siege externally, and was caving in at the same time. I stopped going to school. I hid in the backyards of people in the neighborhood: tree forts, inside covered-over fishing boats, cowering in public bathrooms measuring the time by the automated urinal flushes. I hadn’t been that badly hurt, physically, from the incident I was running from, but the humiliation overwhelmed me. Maybe the worst of it was the conceit that my trap felt unique until I finally stumbled across Mike Tyson telling his own history with bullying on TV. I’d never heard anyone’s experience with it that remotely dovetailed with my own until his. And, somehow, he’d found a way to use cowardice as a weapon and ammunition to make something of himself in the world. He offered me a way out when I was very close to giving up and giving in to the inevitability that suicide was the only viable solution to the torment. Survival mode leaves very little room for compassion or even any meaningful connection with human beings, and without either it’s very difficult to live with yourself. Tyson sent me to a boxing gym and a library and both places saved my life. They gave me a new life and a debt of gratitude I’m very clumsily trying to pay back where I can. I’m sure a great deal of what drew me to Cuba was the David and Goliath dynamic at work with a tiny island taking an impossibly difficult stand against the greatest power on earth. I’d heard Goliath’s side of the story since I was kid, but I’m still trying to come to grips with the 12 years I gave to exploring David’s in Havana.

I want to ask you about your documentary film Split Decision, in which you tracked Cuban boxer Guillermo Rigondeaux on his bouts across the US and Europe. The film seemed much larger than just Rigondeaux’s story — what were you hoping to resolve?

Rigondeaux’s journey chasing the American Dream from a smuggler’s boat fascinated me on a lot of levels, from the universal to the specific. I think the prism of the broken family is the defining feature of Castro coming to power with the revolution, and no family on the island escaped being torn and damaged by the decision that hovered and still hovers over every Cuban’s life, whether to leave or stay. Just like the water surrounding Cuba — there’s a gateway and a fatal barrier, because the Florida Straits amount to the largest graveyard on earth for all those who never made it to their destination. With Rigondeaux’s story, chasing riches and fame as a world champion boxer at the expense of potentially losing his family forever encapsulated, with a lot more money on the table, the same reasons why so many Cubans left. I had no idea, boxing being what it is politically, that Rigondeaux would be able to fulfill his ambitions as a champion and survive at a relatively advanced age as a professional athlete. He made a new life in Miami that changed what he originally said was one of his main reasons for coming to the US: bringing his family over for a better life. Instead, he made a new life with a new wife while, according to him and the family he left behind back in Cuba whom I interviewed, sending money back to support them. They told me “he will never abandon us” back in Havana, but I think in many ways he did. Remember, Rigondeaux’s initial, failed attempt at defection split his family to the core by having his Fidel Castro–supporting father disown him while his mother strongly supported his attempt to make it to the US. She died shortly after his arrival, and he described that agony, along with the journey in the smuggler’s boat, as the most traumatic experience of his life. Again and again, instead of making the US or Cuba the scapegoat or villain, my aim was to make the decision these Cubans are forced to make the villain. The fault lies with both countries’ policies in my opinion. But everything Rigondeaux gave up to “make it” in the US, I think, requires us to understand the value and cost of it in relation to his rewards.

You have an amazing résumé of people that you have met over the years including Lance Armstrong, Slavoj Žižek, and the filmmaker Errol Morris, whom you interviewed for Kindle. I am especially interested in your contact with Gregorio Fuentes, whom you encountered at age 103 in Cuba. It’s one thing to meet and interview celebrities, but Fuentes was the model for the old man in Hemingway’s Old Man and the Sea. What was it like meeting this literary icon?

Gregorio Fuentes, especially at the advanced age I met him, is one of the people I feel the most fortunate to have met in my life. I think the opportunity offered another side to Hemingway that, over time, has faded a great deal, as he’s been transformed into the glib caricature of Midnight in Paris (a movie I still immensely enjoyed)Gertrude Stein once mocked Hemingway in her Autobiography of Alice B. Toklas, saying that he had “passionately interested, rather than interesting eyes.” I’ll take an interested writer over an interesting writer every day of the week. Gregorio, more than anybody I’ve ever met in my life, could lay claim to being born to ply his trade. He shared the passion of fishing with Hemingway for over 20 years, and, in 1961, hearing that his friend had met his end over in the United States, he abandoned fishing for the rest of his life. I found their bond very moving. I don’t think it’s an accident that if you carry a copy of Old Man and the Sea with you around the world, you’ll have people approach you insisting how deeply the story touched their lives. Hemingway and the spirit of Cuba you find in that story somehow seem as timeless as Homer, and yet with the magic and grace of a lullaby. Gregorio, like his country, are primary colors.

What are you up to now and what is next on your project list?

I’m in Las Vegas right now with illustrator and filmmaker Mickey Duzyj reporting on the Mayweather-Pacquiao fight — very much Hunter S. Thompson and Steadman style — with an enormous, fully illustrated piece we’re looking to launch a few days after the fight called The Poison Oasis, easily the most ambitious, daunting piece of journalism I’ve ever been a part of. A film I did for Vice about a female boxer assaulted by Mayweather’s trainer and uncle, Roger Mayweather, will be released shortly after the fight.

It’s a very sad yet inspiring story I think could be very meaningful and impactful for other victims of domestic assault and for awareness of that sickening issue. After that I’m flying to Spain to work on a piece of long-form journalism about the nature of bullfighting today in Spanish culture in the aftermath of the recession. I haven’t been back to Spain since 2004, and it’s a country as dear to me as Cuba in many ways. I was there when they bombed the Atocha commuter train, living about six blocks away. It’s a haunting place, wonderful people and fascinating culture, and I’d like to bring back something to offer from spending some more time there. Bullfighting isn’t something anyone can be on the fence about and the depth of feeling there, within Spain — about it’s cultural place amidst so much controversy with animal rights activists — makes for a compelling insight into perhaps where the country has been and where it’s headed.

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David Breithaupt has written for The Nervous Breakdown, Rumpus, Exquisite Corpse, and others.