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When Cuba and the United States were in the early stages of diplomatic normalization almost two years ago, I went to Havana to cover those aching movements of detente – and explore the city as well. Aside from the throwback tropes of Fidel Castro's country – dated cars, decayed buildings – there were already green shoots of economic reform amid all that Cold War rubble: Construction crews almost everywhere, the earth shaking with gentrification. You could eat delicious, tapas-style seafood in privately owned restaurants or grab a sandwich in a bayside brew-pub.

The most poignant thing I came across, however, though was a black market phenomenon called El Paquete semanal, which in English means The Weekly Package. Few things sum up the contradictions of Castro's Cuba so succinctly.

To this day, Internet connectivity is rare and expensive, the old-fashioned, hiss-and-squelch of dial-up service exclusive to the island's elites. At the same time, there is a massive appetite for culture beyond the cultural firewall. One ambassador I had interviewed told me that the younger generation was obsessed with U.S. pop culture and bought thumbdrives, or paquetes, full of TV shows, films, and magazines through the black market. A young Cuban staffer in his embassy had told him about the underground phenomenon, and the ambassador suggested that if I didn't name the worker or identify the embassy for which he worked – and maybe bought the kid a Coke and a burger – the staffer would show me how it worked.

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Over lunch, the young man – call him Carlos – told me about his fears of the American takeover of his island and indifference to the Castro brothers. Carlos, however, was much more enthusiastic about his love of U.S. television programs such as The Walking Dead, and was already episodes ahead of me on Homeland. I asked him not to spoil any episodes.

The various contradictions reminded me of Fidel Castro himself, arch-foe of Uncle Sam but like many of his compadres, a lover of béisbol (baseball), who may even have pursued a career in the sport. Even before the Socialist strongman seized power, Cuba had the same duality: a cultural affinity of two countries only 90 miles apart, but also estranged siblings, sharing the same DNA but also the kind of enmity and suspicion reserved for big and little brothers.

In the sleepy, residential area where the paquetes were made, there was a line about nine or 10 people deep outside an open door, ground-floor apartment. Most of the clientele appeared to be in their twenties and stoical in that uniquely Socialist way to a long wait. No one seemed perturbed about a possible raid.

It was a family-run operation, mother and two sons at their desktops busily scrolling through pages of content, clicking and dragging titles to thumbdrives. One of the sons told me in Spanish that each order took around half an hour to fulfill. The cost was the equivalent of two to three Canadian dollars, not a small amount in country where the average monthly wage is $30 to $35.

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The little room was also humming with brand new hard drives and servers, but the mother and sons didn't want to reveal how they got them. While they didn't seem to worry about the lines giving them away, some larger more instinctive fear prevailed. Maybe they were not used to prying journalists, or worried I was not a journalist but someone with the ulterior motive of looking for the larger player.

But one of the sons still believed I was really a Canadian journalist. He said they did well here, but he just wanted to move to Montréal. In Spanish, he told me his dream was to live in North America, speak French and live freely. Carlos, who wanted to stay on the island, disagreed. He always wanted to remain there.

On the day after Castro's death was announced several headlines observed that that younger Cubans were indifferent to the event. On this subject, at least, the two young men would have likely agreed. And they, too, are still waiting for President Raul Castro to tear down that firewall.

Craig Offman is The Globe and Mail's Arts editor. Follow him on Twitter @Craigoffman.

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