After the basic facts are covered the interpretation must happen – the hunt for images that not only say, ‘Fidel was here,’ but those that convey why, and what this moment means.

Cuban President Fidel Castro casts a distinctive shadow on a balcony in Santiago de Cuba during a 40th anniversary speech made from the same rail where he addressed crowds after winning the revolution in 1959.

“When Fidel dies I am dropping everything and getting on the next flight to Havana,” my friend and photojournalism colleague Phillippe Diederich proclaimed over several beers sometime around the turn of the millennium.

“¡Yo también, compay!” I slurred, punctuated with a fist pound on the bar table.

At least that’s how I remember beer- or rum-soaked conversations that repeated themselves several times over the next 5 years. We were steeped in Cuba then. The “Special Period” after the fall of the Soviet Union put much attention on what would happen in Havana and the hemisphere after El Comandante en Jefe Máximo expired. Phillippe was on and off the island, producing photo essays on its Harley riders, covering first papal visits for the New York Times and starting a novel which is set then and there.

I went four times over the next three years, the first to photograph Fidel’s speech on the 40th anniversary of his revolution. It was an incredible assignment to document a man who, with his band of barbudos, wedged a small island nation between two superpowers and had refused to leave, give up or die for decades. Fidel had been an unpredictable-turned-obdurate symbol of the Cold War.

Everything about that first trip was nostalgic for classic (or mythic) photojournalism. I was pulled aside in Cuban customs and interrogated for what seemed like an eternity about a small gift-wrapped package in my bag. “It’s a birthday gift for a colleague,” I explained. “You can open it if you like.”

“No no no. We won’t do that. So why are you here again?”

“I am here to photograph the anniversary speech in Santiago, for the New York Times.”

“Oh! The New York Times! So what’s in this box again? Who is your colleague again? Can we call her?”

“Yes. A gift. Feel free to open if it you like. It’s for the Tribune Company correspondent. Yes, you may call her. Would you like her number?”

This cycle repeated five or six times until they let me through, not accepting my offer to open the gift for them, and not calling my dear friend who was stationed in Havana. No money changed hands either. My oldest friend had come along, too, for sport and curiosity. He waited for me, puzzled, outside of customs.

On New Year’s Day, 1999, we climbed aboard a decaying Tupolev Tu-154 passenger jet flown by Cubana de Aviación. The creaking air conditioning steamed, the seat-back locks were broken in the reclined position. The toilets were locked shut, bleeding fecal aroma into the cabin. The hand-me-down Soviet plane was almost as old as Fidel’s revolution.

That night I stood among the crowd gathered in the central plaza below the same balcony where Fidel had greeted the masses 40 years earlier. El Jefe walked out fashionably late, waved, fist pounded and pontificated for several hours about el período especial and the imperialistas on the base across the bay.

Supporters cheer for Castro.

All images © Kevin Moloney, 1999

I photographed for the first 30 minutes before I had to leave to develop color film in the hotel bathroom, scan and tone color images on a grayscale laptop and upload them at only 2400 bits per second over ancient Cuban phone lines to New York. Each image took almost a half hour to transfer, and I got two images through before the late edition deadline. I was beat in all the earlier editions by wire photographers using gigantic new digital cameras that cost as much as my whole bag of Leicas.

Standing in front of the world stage has always attracted young photojournalists. The importance or attention surrounding an event like this adds weight to every decision and frame you make. I photographed in inverted-pyramid style, making nut-graph images of Fidel waving and speaking from the podium, the rapt crowd and the excitement of the event. But that can take mere moments at a scripted event where little is likely to change. After the basic facts are covered the interpretation must happen – the hunt for images that not only say, ‘Fidel was here,’ but those that convey why, and what this moment means.

That’s when I saw his shadow. By 1999 the septuagenarian insurgent was a frail old man. He was gaunt and no longer intimidating. A strong gust of wind could have accomplished what the CIA had attempted for the entire 1960s. But his shadow, stretched a bit by the angle of light, was the Fidel of the Sierra Maestra, the man who had scolded the UN and kept American influence out for decades. That was the picture. A shadow of the Cold War.

For the next week my two best friends and I wandered Havana, soaking in its cigars, rum, anachronisms and relishing in the rusty, smoke-belching ghosts of American influence. The only contemporary sign of my country was the in the ‘gringo green’ bills that changed hands on an officially blessed special-period black market.

Once, Phillippe and I waxed fantastic about what it would have been like to bushwhack our way into the Sierra Maestra in 1958, find the revolutionaries and photograph their march onto the world stage. Fidel died yesterday, just as I and colleagues Chip Litherland and Rob Mattson — my former students — and Ross Taylor traded stories of our trips to Cuba. Today is the day that I swore I would be on the next plane to Havana. But I am not, and neither is Phillippe.

Since those effusive conversations years ago, Fidel has passed power to his brother who already has plans in place for his own retirement. The Obama administration pried open a diplomatic door that has a rusted lock. Cuba is now just a curiosity. What Phillippe and I imagined would be a historic change event will come and go in a set of lead-story obituaries and a little bit of news analysis. Tomorrow the media’s eye will be back to a power transition that’s more timely and arguably less predictable than Fidel’s. The obdurate symbol has left the balcony.