Nothing Like A Havana Hangover: An Interview With Randy Richardson

Nothing Like A Havana Hangover: An Interview With Randy Richardson

By WC Turck

I came to know Randy Richardson through his work as a founding member and president of the nonprofit Chicago Writers Association and, since then, have followed his journey as a photographer and writer. On Facebook, during the pandemic, he began posting these stunning, sometimes otherworldly, photos capturing Chicago’s North Shore lakefront at sunrise. His novels have always been firmly grounded in very specific places. In his debut, Lost in the Ivy, that place was Wrigleyville, the neighborhood surrounding Chicago’s North Side baseball team’s iconic stadium, Wrigley Field. In his second novel, Cheeseland, Richardson took the reader on a wild road trip through southwest Wisconsin. In his photography and in his writing, Richardson had never veered too far from his home, in Evanston, Illinois. Then came Havana Hangover, his latest novel, where he takes the reader on a page-turning adventure to the island nation of Cuba, a country, in many ways, frozen in time. Once again, place is key. The once-forbidden country infuses every bit of Richardson’s telling of two estranged friends who reunite for a bucket-list trip where little is at it seems. With evocative descriptions of the people and place, and fascinating historical tidbits tossed into the mix, Havana Hangover delivers one surprising twist after another. I caught up with Richardson to talk about his writing and publishing journey and the true story behind his latest novel.

Tell us about your publisher, Renegade Press. How did you find them?

I was listening to the Chicago Writes Podcast, which, of course, you host, and you were talking with actor, screenwriter and filmmaker Dan Davies, who had just launched his own independent publishing company, Renegade Press, based in Appleton, Wisconsin. He was talking about his model for the press, which is to not only publish books but to take those books and adapt them into screenplays to sell to Hollywood. That’s when my ears perked up. The moment I finished listening to the podcast, I sat down at my computer and typed an email to Dan. I started by mentioning that I had heard him on the Chicago Writes Podcast. Then I noted that I’m the president of the Chicago Writers Association, which launched the podcast. I went on to pitch my thriller, Havana Hangover, as a novel that could be easily turned into a movie or limited series. Not ten minutes later, I received a response, which never happens with agents or publishers unless it’s an autoreply, which this wasn’t. He said he liked the concept and asked me to send him the first few chapters. About a month after that, he followed up and asked for the complete manuscript. And about two months after that, he texted: “Renegade Press wants your book!” The words every author wants to read! You didn’t know it at the time, but you served as the matchmaker who brought this author and that publisher together.

This is your fourth book and third novel. What have you learned about writing fiction over the years?

I think that, more than anything, I’ve learned to be more patient with my characters, allowing them to develop more fully as their stories are told. And in the case of Havana Hangover, I kind of think of the place as being one of those characters. The story is told through the eyes of Tanner, and we’re seeing not only his character grow as the story unfolds, but we’re also seeing the characters surrounding him and the place he’s in grow with him. Through every chapter, the fuzzy picture that we have at first becomes a little clearer. 

What was the inspiration for Havana Hangover?

All of my writing is, to some extent, inspired by pieces of my life. For Havana Hangover, that piece began in November 2016, the first time I traveled to Cuba. Two historic events collided during the time of my travels. On the same morning I left for Cuba, my favorite baseball team, the Chicago Cubs, won their first World Series in 108 years. On the same morning that I returned to the states, the U.S. presidential election results had just been decided. Those two events served as a springboard for the story that became a runaway adventure with many twists and turns where little is as it seems. The characters behind it were mostly inspired by real-life people, including me and my travel companion, a friend whom I’ve known since law school, and our tour operator and tour guide. But the real seed for the story was planted on our second trip to Cuba, the following November. It was on that trip that my friend and I had been out on the town and, at some point, we were separated. I went back to our casa particular, a Cuban bed-and-breakfast, and went to bed. The following morning, I woke to a string of text messages from my friend. The last of those messages said: “Help Me!” I won’t go into what actually happened – it’s a long story – but as you can imagine I sprung out of bed and fortunately found my friend asleep in the other room. But that little jolt became the starting point for my story of a disoriented narrator. From there, the story is all fiction, including the back story of the complicated history between the protagonist, Tanner, and his missing friend, Jackson, who, it turns out, might not be his friend at all.

How has travel impacted your writing? Could you have written about Cuba without having spent time there?

Of course, you could write about Cuba and Havana without having ever stepped foot on the island. But I don’t think that it would be possible to paint the real story without actually having been there. Between 2016 and 2019, I traveled to Cuba and stayed in Havana four times. I walked most of those streets I write about. Not just once, but many times. Each time, I saw, smelled, and heard something new. There’s so much going on there that it is easy to miss those little details. I wanted the reader to experience what I had experienced, so that they could understand what makes it a place that kept calling me back every November. The people, the architecture, the music, the history, and, of course, the classic cars. When I take the reader along for a ride in a canary-yellow Chevy convertible along Havana’s Malecon, the seven-kilometer-long seawall, I wanted them to feel what I felt when I made that same trip. I don’t think I could have captured that if I’d only read about it and not actually experienced it.

Instead of spending a lot of time on main characters’ backstories, you thrust the reader into the action right away and heighten their histories as the plot unfolds. Did you know the characters backstories when you started the novel or did those backstories emerge during the writing? And how do you develop your characters on the page?

The characters’ backstories evolved as I wrote the novel. Because the story is told in a first-person narrative, it is told entirely through the eyes of the protagonist, Tanner. In order to understand him, and the characters surrounding him, I used those backstories to develop their characters. Without those backstories, the reader wouldn’t have been able to understand who they are today and what drives them.

Most of the characters I write are inspired from my own world. I think that helps to make them feel authentic. But then of course, I put them into situations that ordinary people would not typically find themselves in. It’s fun to play with them, to see how they react. In building them, my editor, Katherine Don, kept pushing me to dig deeper into their histories and motivations. You begin to see how they’re all very flawed characters, which, I think, makes them relatable.

Do you outline or let the story unfold organically? Or some combination of the two?

I’ve never had an outline for any of the three novels I wrote. That’s not how my mind works. And honestly, I don’t think I could write a novel with an outline in front of me. To me, the fun of writing fiction is finding where the story takes me. I think if I already knew where that was when I started, I’d get bored and never finish it. That said, because I don’t work from an outline, I think the importance of having a developmental editor to keep the story on course is absolutely critical. Katherine, my editor, was a great pilot. She saw things that I couldn’t see and helped me fill in all of the plot holes and get the story back on course whenever it veered.

In Havana Hangover, you keep upping the tension, taking your protagonist deeper into a web of intrigue and danger. And then there’s the love angle that harkens to Mickey Spillane and femme fatales in classic crime dramas. Talk about building layers of tension in a story.

Havana Hangover is a slow build. The reason for that is that it is told through the first-person narration of Tanner. He’s the protagonist and of course, in the beginning, he doesn’t know what he’s gotten himself into. There’s a lot of alcohol involved which also makes him somewhat of an unreliable narrator at times. He’s disoriented as he’s trying to put the puzzle together himself. Then the action suddenly takes off when he sobers up and those pieces do start to come together. He’s taken on a wild ride through the streets of Havana that eventually lands him in the corrupt corners of D.C. politics. Because the reader is taking this ride with him, you feel those ups and downs and jolts of the roller-coaster he’s on.

Anabel and Tanner have a complicated relationship. What does he see in her?

Well, for one, she’s beautiful. And smart. But I think it is much more than that. At least at the beginning, she’s everything that Tanner isn’t. She is strong-minded and bold. I think Tanner wants to be more like her, and she helps him find that inner strength in himself. There’s a backstory scene where she helps him with his anxiety in law school, and I think in that scene you see that she does really care about Tanner – even if she knows that at some point, she’s going to hurt him.

Is the Lourdes spy base that you describe in the book a real place or a fictional creation? If it does exist, were you able to visit there?

Lourdes was – and maybe still is – very real, at least from what my research tells me. During the Cold War, it was said to be the biggest Soviet overseas listening post. Reportedly, Vladimir Putin closed it in 2001. However, I read some news stories suggesting that he might have reopened it in 2014. But, no, I haven’t been there. That is one of the few places in the novel that I had to mostly imagine on my own, using what little I could find about it in my research.

Taking the narrative there builds in the history between the United States and Cuba. Having been to Cuba and met the people, what are your feelings about opening Cuba to direct travel from the United States, and do you think Cuba could handle a sudden opening between the two countries?

Well, there was a reopening in 2016, which President Obama brought about. That’s what brought me to Cuba in the first place. There were some hurdles, but they were easy to clear. Even some of the cruise ships out of the U.S. started to dock in Cuba. That brought a great amount of hope to the people of Cuba, who needed that injection of hope more than anything. But then President Trump tightened the clamps on U.S. travel to Cuba. While you could still travel to Cuba directly from the U.S. (I continued to do so through 2019), Trump made it much more difficult and I think most Americans thought that they couldn’t go there at all. As a result, tourism in Cuba took a major hit after Trump. Then the pandemic struck and cut off all travel to the island country. Cuba has yet to recover economically from that one-two knock-out punch and I’m not sure it ever will. Life there has gone from bad to worse. Sadly, all the hope that came in 2016 has turned into despair. Most of the young people there have left or are trying to leave. All of the friends I had made there are now gone. They’ve fled the country for Europe, Mexico, or the U.S.

Jackson tells Tanner, “Your ridiculous worship of Hemingway made for an obvious excuse to convince you to come with me to Cuba…” In the Afterword, you mention Hemingway’s favorite bar in Havana. Did Hemingway’s writing inspire your travels to Cuba?

That part of Tanner’s character is very much me. I’m one-hundred percent a Hemingway fanboy. I’ve read just about anything he wrote, have all of his books and Life magazine covers, and followed his footsteps to just about anywhere he lived and wrote about. So, of course, Cuba was always on my bucket list. When I first started looking for a tour operator, I specifically searched for someone who did customizable tours and when I found one, I told them that the tour had to include stops at Hemingway’s Cuba home, Finca Vigia, where his boat, Pilar, is on display, and also to his two favorite watering holes in Havana, La Bodeguita, where he drank his mojitos, and to El Floridita, where he drank his daquiris.

No spoilers here, but obviously, we aren’t finished with Tanner, right? Is there a future for him as a series, or is this a stand-alone story?

No, I don’t think Tanner’s hangover is over just yet. I can’t leave him how I left him at the end of the story.

Will you return to Cuba or will we see Tanner someplace else in the world?

I’m hoping to return to Cuba this fall. We’ll see…As for Tanner, I think his story will take him to new places. I haven’t yet started on the sequel but, in my head, I see him in Miami and Mexico City.

What’s are you working on next?

This summer, my publisher, Dan Davies, and I are collaborating to write the screenplay for Havana Hangover. If all works out, you’ll be seeing Tanner on the big screen or streaming on Netflix in a couple years. Fingers crossed!


Randy Richardson’s latest novel, Havana Hangover, published by Renegade Press, is available in paperback and can be ordered from you local indie bookstore or online. It’s also available on Kindle at Amazon.com.

WC Turck is an author, artist, and host of the Playtime and Chicago Writes podcasts.


Hypertext Magazine and Studio (HMS) publishes original, brave, and striking narratives of historically marginalized, emerging, and established writers online and in print. HMS empowers Chicago-area adults by teaching writing workshops that spark curiosity, empower creative expression, and promote self-advocacy. By welcoming a diversity of voices and communities, HMS celebrates the transformative power of story and inclusion.

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