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Cuba Finally Connects To The Internet. Too Bad The U.S. Has Disconnected From Cuba.

Desmond Boylan
Cubans in Havana sit at a government-designated WiFi hotspot trying to get Internet connections.


Four years ago this month I sat in a Wynwood restaurant with a bunch of rookie Cuban entrepreneurs and watched their eyes bug out.

A Miami online retailer was showing them how to do commerce on the Internet – that is, if Cuba’s communist regime ever let them have that kind of access to the Internet. Cuba then was one of the world’s most unconnected countries: only 5 percent of its population was wired. Especially frustrated were cuentapropistas – small business owners like clothes makers who dreamed of riding the World Wide Web to find raw material, lure new customers and score fat cybersales.

On Wednesday, Cuba’s glacial government finally legalized Wi-Fi – including the importation of hardware like routers – for private Cuban homes. And, just as important, for private Cuban businesses.

READ MORE: Googling Cuba: Is the Communist Island Ready to Join the World Wide Web?

Wi-Fi’s new legal status is a potential boon for the island’s cyber-handcuffed entrepreneurs. That in turn could have been a win for U.S. Cuba policy, which supposedly promotes cuentapropismo as a means of making Cubans more economically and socially independent of their stifling state.

But the sad, ridiculous reality is that just as Cuba and its tech-conscious President Miguel Díaz-Canel are granting cuentapropistas an Internet edge, the Trump Administration is doing everything it can to dull it.

The sad, ridiculous reality is that just as the Cuban regime is finally granting folks an Internet edge, the Trump Administration is doing everything it can to dull it.

In fact, it’s hard to tell these days who’s the bigger impediment to Cuba’s fledgling private sector. Is it the communist comandantes in Havana who put the bootheel on go-getter restaurateurs and accountants whenever their success starts looking too capitalist? Or is it the crabbed cold warriors in Washington who, when they tell us they’re smacking the Cuban regime, end up punishing the island’s industrious beachwear manufacturers and short-term room renters?

This year we’ve already seen disturbing cuentapropista data related to President Trump’s efforts to put the squeeze on Cuba – a strategy meant to please a shrinking but still influential cohort of hardline Cuban exiles in Miami whose votes he believes won him Florida in 2016 (and whom he’s counting on in 2020).

Two years ago Trump re-tightened restrictions on U.S. travel to Cuba. He said it would bleed revenue away from Cuba’s state- and military-run tourism businesses. But Cuba’s private entrepreneurs have experienced the hemorrhaging instead. By forcing Americans to visit Cuba in official tour groups, for example, Trump pushed them away from independently operated tourism enterprises – not to mention independent businesses that supply them.

According to Cuba’s tourism ministry, the occupancy at bed-and-breakfasts and other private lodgings in Cuba plummeted 44 percent last year. It's not likely to look any better this year.


That’s more probable now that Trump has yanked back the remittances Cuban-Americans can send to the island – from an unlimited amount to just $1,000 every three months. Given the absence of financing sources in Cuba’s lame statist economy, most of its more than half a million cuentapropistas have relied on the larger flow of dollars as a capitalization lifeline.

Another blow is Trump’s drastic reduction of U.S. visitor visas for Cubans – which used to be good for five years and multiple entries but were recently slashed to three months and only one visit. For many Cuban entrepreneurs it’s become vital to make regular trips to South Florida, where they have supplier and training relationships with businesses in communities like Hialeah.

Credit Tim Padgett / WLRN.org
Miami online retailer Mel Valenzuela gives visiting Cuban entrepreneurs an Internet commerce tutorial in 2015.

My more conservative Cuban exile friends argue that moves by the regime like Wednesday’s Wi-Fi liberalization are proof Trump’s pressure tactics are working. They insist I look at the new economic crisis bedeviling said regime as a sure sign the island’s totalitarian wall is about to fall.

But I’ve heard that claim made so often – and so mistakenly – in my 30 years covering Cuba that I’m just not taken in by it anymore. Cuba won't likely see genuine change until its revolution’s geriatric founders have disappeared. And then only if the country’s civil society has been boosted enough in the meantime to convince younger leaders like Díaz-Canel that political and economic democratization is the only alternative.

It was supposed to be the U.S.’s crucial role to help pump up those Cuban dissidents, independent journalists and especially private entrepreneurs. But Trump’s return to a policy of isolating rather than engaging Cuba has made that harder – and just when the regime is wiring Cubans to the Web.

Sure, the regime will still control the Internet in Cuba. Even so, Cuba’s cuentapropistas could have ridden the island’s connection to the Web more robustly if the U.S. hadn’t cut its connection to the island.