🇨🇺 What the Cuban Revolution Can Teach the Democratic Party

Reflections from The Live Drop, Episode 71 with Kit Turner

Another Live Drop Commentary

By Mark Valley

When Kit Turner joined me on my podcast The Live Drop to talk about his historical fiction novel Children of Outer Darkness, we weren’t planning to sketch out a roadmap for democratic renewal in the United States. But the story of the Cuban Revolution—its improbable origins, diverse cast of insurgents, and eventual triumph over a brutal authoritarian regime—offers surprisingly resonant lessons for anyone watching American politics today, especially those hoping to energize the Democratic Party.

Let’s be clear: the Democratic Party is not leading an armed insurgency. But if it hopes to counter the creeping authoritarianism of MAGA populism and reclaim a meaningful majority of hearts, minds, and votes, it may need to think like insurgents—those who win by embedding with people, understanding their pain, and building trust in unlikely places.

🏞️ Lesson One: Revolution Starts with the People—Not the Elite

As Turner notes, Fidel Castro’s revolution didn’t begin with tanks nor communism really. He described his goals as nationalist, anti-corruption, and anti-dictatorship. The Marxist Revolution wouldn’t arrive until 1961 after he’d weighed his options... but it all began in 1959 with 83 half-trained fighters on a leaky yacht, scattered in the mangroves, hungry, disoriented, hunted. They were doomed by most accounts. And yet, they survived, adapted, and gained a foothold in the Sierra Maestra mountains, not through sheer force, but by aligning with the local population.

The Democratic Party, by contrast, still struggles to speak to rural America, to disaffected voters in red or purple districts, to those who feel resentful, abandoned or misunderstood. A peaceful insurgency doesn’t begin in conference rooms in D.C.—it begins on Facebook, then on porches, in town halls, at the local Walmart, and yes a local diner if CNN or Foxnews isn’t already there. If your movement can't survive without a motorcade and a protective detail, it’s not really a movement.

🌎 Lesson Two: Coalitions Win—Even Messy Ones

The Cuban insurgents weren’t ideologically uniform. Castro had to juggle this coalition. Some were far left, some were centrists, some were wealthy students rejecting their own privilege. Che Guevara wasn’t even Cuban. Turner paints a portrait of a coalition that held together not because it was ideologically pure, but because it was strategically focused: oust Batista, return power to the people.

Democrats often splinter into micro-factions—progressives vs. moderates, urban vs. rural, reformers vs. institutionalists. The lesson? You don’t need unanimity. You need a unifying mission—a clear, urgent “why”—and the discipline to keep your coalition intact until the mission is complete.

🕵️‍♂️ Lesson Three: Outside Help Matters—But Must Be Controlled

One of the more surprising insights from Kit Turner’s interview is how many foreign actors had a hand in the Cuban insurgency: the CIA, Soviet agents, Cuban exiles in Florida. Castro took what he needed from each, while keeping the revolution’s identity distinctly Cuban. He was careful not to appear as anyone’s puppet, knowing that perception is as powerful as policy.

Today’s Democrats might take help from major donors, national PACs, or outside organizations. But the message, the branding, the voice—that has to stay local. You don’t build trust in NY-21 or in Ohio or in Arizona by parachuting in national talking points. Every community must feel that the movement is theirs.

🎙️ What a Peaceful Democratic Insurgency Might Look Like

1. Hyperlocal Listening – Treat every voter as a source. Ask more questions. Knock on doors without scripts. Don’t convert, connect. Ask questions. Be curious.

2. Unlikely Candidates – Recruit from the ranks of nurses, teachers, contractors, veterans, small-town mayors and council members—not just law school grads with résumés. The best insurgents are people who belong before they run.

3. Flexible Messaging – National values, local accents. Keep the mission consistent, but let the tone change by district. A good insurgency doesn’t broadcast—it whispers what people need to hear.

4. Decentralized Action – Encourage regional experiments. What works in Buffalo may not work in Boise. Give people tools to test the landscape, not orders.

5. Propaganda with Purpose – Yes, that’s right. Propaganda. Use social media, storytelling, podcasts (ahem) to tell the story of the movement. Make it compelling. Make it real. I’m repurposing The Live Drop soon in this effort.

📚 Final Thought

As Kit said in our conversation: “The real story is the story that came before.” We fixate on Castro’s later years—on the missile crisis, the repression, the speeches—but we forget that his victory came from unlikely beginnings. A few idealists, some old rifles, and a dream that just wouldn’t die.

So here’s the question: Are Democrats ready to get off the yacht, get muddy, and build something from the ground up? If so, the history books—fictional and otherwise—might have a few pages left to write about another diverse band of patriots who want their country back.