Smerconish on Cuba: “It’s All Different Shades of Gray”

Jono Matusky
ifCuba
Published in
4 min readAug 17, 2016

Photo copyright Christopher P. Baker

This story was originally published on ifCuba.com

Michael Smerconish, radio host, CNN anchor and journalist for the Philadelphia Inquirer, recently traveled to Cuba with this his family for a chance to see the country before it inevitably changes. This wasn’t the first trip for Smerconish — he had previously traveled to the island nearly fifteen years prior to interview Fidel Castro.

We had the opportunity to sit down with Smerconish in a quite cigar shop in the Vedado neighborhood of Havana. As he enjoyed a Ribaina cigar, he told us what it was like to return, what intrigues him about Cuba today, and where he thinks the country is headed.

Smerconish first visited the island in January of 2002, just a few months after September 11th. A journalist for Philadelphia’s Daily News at the time, he joined a delegation led by the late Senator Arlen Specter of Pennsylvania. He was one of a group of six, their goal to interview Fidel Castro.

“We spent seven hours with Fidel,” said Smerconish of the trip. “We were never sure if the meeting would come off until we got here. It did.”

“I had this very privileged and unique experience. That was my introduction to Cuba. Total time on the island was less than seventy-two hours.”

Intrigued by this short trip, Smerconish always wanted to go back for a lengthier stay. Encouraged by the changes put in place by the Obama administration, he decided to organize a trip for his family. “I’d always had the idea of wanting our kids to see Cuba before things forever change.”

“I’m also obviously interested in the politics of it all.”

Smerconish reached out to Chris Baker, a travel writer and photographer for National Geographic who had recently appeared on Smerconish’s radio show. Baker literally wrote the book on Cuba, authoring numerous travel books and guides. He offered to help coordinate the trip and serve as an expert guide, providing Smerconish and his family a unique look inside the country.

On his first trip, Smerconish never made it out of Havana, and on his second visit he was particularly struck by the beauty of the Cuban countryside.

“I said yesterday that Cuba makes me want to paint…When we were in the countryside, the richness of the colors, to see the soil and the vegetation and the mountains and the sky…all in the same frame, it’s just stunningly beautiful.”

Beyond the beauty of the countryside, Smerconish was also intrigued by the people. He was struck by the spirit of entrepreneurship in Cuba, which overturned his “stereotypical, socialist” assumptions towards the Cuban people.

“Everywhere there are examples of entrepreneurship.” Smerconish cited numerous examples from his stay. He likened Uber in the United States to the Cuban almendron system, a private cooperative of taxi drivers who provide a patchwork form of public transportation.

To keep these taxis running, the island relies on an army of resourceful private mechanics, who Smerconish described as magicians. Their ability to make anything work, with such limited resources, particularly struck him. “Their inventiveness is really amazing.”

He saw this entrepreneurial spirit everywhere, from merchants selling cheese and butter on the side of the road to families running the government owned cigar factories. A cigar lover, Smerconish visited the Robaina family tobacco farm and met the grandson of the founder of the company. In the decades since the revolution, the family continues to run farms and factories for the Cuban government, but also operate their own private enterprises outside the country to secure their international brand and grow their business.

Smerconish never expected to witness this level of entrepreneurial ingenuity in Cuba, a country with countless challenges and complexities. “I have a tendency to see things in black and white,” said Smerconish. “There’s nothing black and white about it but rather different shades of gray.”

“I’m not sure what to make about the future of Cuba. My hunch is that the country will not go backward and will instead continue the great change that is currently taking place. Whether it’s the change that some in America would like to see, I have my doubts. I think a lot of what’s gone on in the past 60 years is engrained in the Cuban psyche. I’m not sure how much Cubans, particularly those outside of Havana in the countryside, want the sort of change that outside influences will bring about. Maybe there’s a happy medium in there where entrepreneurship and capitalism can coexist with the ration book, I don’t know.”

“I wish I had a crystal ball to know how it all ends. I just want to be around to see it.”

Read more about Michael’s trip to Cuba in his recent article in the Philadelphia Inquirer.

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Jono Matusky
ifCuba
Editor for

Inventor, creator, entrepreneur. I work with entrepreneurs, to help them do what’s never been done before. More info at: www.jonomatus.ky