Skip to main content

Five Years After Obama’s Historic Détente With Cuba, What Trump’s Prohibitions Have Meant for Music

"In general, the narrative about Cuba is not as sexy or optimistic," Cuba Educational Travel's Collin Laverty concedes. "[But] when you look at a crowd that size, dancing, smiling, crying for five…

It’s been five years now since then-President Barack Obama announced that diplomatic relations with Cuba would be restored for the first time in more than half a century. The response from music artists following the Dec. 17, 2014 milestone was loud. In March 2016, Major Lazer played an outdoor concert in Havana for half a million people. Then the Rolling Stones gave their first-ever show in Cuba, a massive free event that for many Cubans symbolized the dawn of a new era.

“I was there at the Rolling Stones concert,” X Alfonso says now. A well-known rapper, rock musician and producer in Havana, Alfonso is behind the creation of Havana’s La Fábrica de Arte Cubano. A cultural center and concert venue, La Fábrica opened in 2014, and in the heady period after the détente, was visited by artists from Katy Perry to Will Smith, Childish Gambino and Jon Bon Jovi.

“I remember saying ‘this is the start of a great change, a big advancement,'” says Alfonso of the historic night he stood for two hours watching the Stones. “And then not only because of Los Rolling, but because of the amount of artists who started coming to Havana, the size of the audiences, the amount of business people and beautiful people, who started making relationships with Cuba.”

But another change came after Donald Trump was elected in 2016 and quickly set about reversing Obama’s Cuba policy once he took office in 2017.

“The current regulations impact everyone from would-be travelers to investors and promoters.” says Collin Laverty, president of Cuba Educational Travel, which organizes frequent music-focused trips to Cuba.


The 2014 accord between Obama and then-Cuban President Raul Castro had been followed by policies that facilitated investment in Cuba and travel to the island, and allowed commercial flights and cruise ships from U.S. destinations to commence service to the island. New hotels opened, Airbnbs were cheap, and with increased tourism came new opportunities to entertain visitors for whom Cuban music is a major draw. Music tours of Cuba mushroomed. For a while it seemed like major artists were lining up to stage the encore to the Stones in Havana.

While the U.S. embargo (which was put in place in 1962) has never been lifted, and commercial tourism in Cuba was still technically prohibited under the Obama administration rules, any American could, for the first time in decades, book their own trip to the island rather than signing up for chartered tours with specific cultural, religious or academic activities. Travel to Cuba was no longer shrouded in mystery and intrigue.

“It was a Camelot in the Caribbean,” attorney Pedro Freyre, an expert on United States Cuba policy who heads the international practice department at the Akerman law firm in Miami, says of the period before the Trump administration closed the door that Obama had opened. “The great shining moment. That impetus is completely gone. There are a few companies that are in niche situations that continue to have Cuban involvement, but the entire effervescent scene, with executives looking for business on planes every day into José Martí [airport in Havana], the sense of excitement and opportunity is basically gone.”

Trump announced his new policy on Cuba in 2017, and a series of travel regulations and economic sanctions have since been put in place. U.S. Cruise ship routes to Cuba were abruptly terminated by the administration last June. Earlier this month, the American government announced that commercial flights from the U.S. to Cuban cities other than Havana were being suspended.


After a record year in 2017, with a reported 600,000 Americans visiting Cuba, Cuban officials recorded a significant drop in U.S. visitors in 2018. The Cuban Minister of Tourism announced earlier this month that current U.S. policy had “directly impacted tourism” in 2019, with a 5.2% further drop, from 460,288 visitors to 436,453, from January to September over that period in 2018.

A current U.S. State Department “restricted entities” list includes dozens of restaurants, bars and hotels owned by Cuban state-run companies that Americans are now forbidden from patronizing under threat of fine. Also on that list is Havana’s Abdala recording studio, and a record label and music publishing company.

For now, Americans can still go to Cuba to take in a concert or festival, but trips must fall under a provision called “support for the Cuban people” which requires an itinerary of activities amounting to “meaningful interaction with the Cuban people,” in the majority of cases put together by an approved travel agency, organization or university.

“You have to be careful not to go to prohibited hotels or engage in prohibited transactions,” says Bill Martinez, a Bay Area attorney who specializes in visas and other tour paperwork for international artists, and has worked getting American musicians to Cuba and vice versa for several decades, during which he has followed the changes in Cuba policy under various presidential regimes. “Some people now say it’s not worth the hassle.”


For some high-profile artists, it’s also not worth the risk of incurring violations, or perhaps unwittingly making a political statement by the mere fact of performing in Cuba in the current political climate. For example, just after Trump announced new restrictions, country music star Tim McGraw canceled “One of Those Havana Nights,” “four days of music and adventure” that had been announced for 2019 Memorial Day weekend. With ticket prices ranging from $2,599 to over $5,000, the trip included performances by Cuban artists Los Van Van and Carlos Varela as well as McGraw’s central concert, luxury accommodations and VIP perks like a ride in an old American convertible.

The organizer of that “immersive experience,” Dreamcatcher Events, which promotes similar artist-fan confabs in other locations, had previously produced Havana encounters with Blondie, Rufus Wainwright and Ben Folds. The terms of the U.S. embargo have always required that American artists allow the Cuban public to enjoy their music free of charge, but with Americans being able to get to Cuba without a hassle, the staging of such package tours had emerged as a viable business model for artists who wanted to perform in Havana during the Obama years.

Danny Heaps, the company’s owner, told Billboard in an email that the Dreamcatcher’s Cuba venture is currently “on hiatus for geo-political reasons.”

“Now the process [of performing in Cuba] is so cumbersome people are saying ‘why should I do it?'” comments Freyre. “And ‘who is going to be my audience?’ Because you are no longer going to have have so many other Americans around. So what is the revenue model?”


While the political climate is not encouraging, artists could look to the precedent set by others to still make performing in Cuba financially feasible. Audioslave, which played a pioneering concert in 2005, filming the concert for a documentary distributed on DVD. A companion album has been streamed 92.2 million time in the U.S., according to Nielsen Music. Major Lazer‘s own film, Give Me Future, spawned an album of the same name that has garnered 1 billion U.S. streams, and rose to no. 11 on the dance albums chart in 2017. The Rolling Stones, whose Havana concert cost a reported $7 million to produce, was bankrolled by a wealthy attorney. The Stones’ live album, Havana Moon, together with a concert film, was released about six months after the group’s show. The recording racked up 1.1 billion U.S. streams. Wynton Marsalis took his Jazz at Lincoln Center Orchestra to Havana in 2015. The band’s Live in Cuba album peaked at no. 2 on both the Jazz albums and Traditional Jazz Albums charts and has had 2.9 million U.S. streams.

Laverty’s Cuba Educational Travel is among the organizations that have so far not let Trump’s tightening of the embargo deter them from bringing artists and audiences together in Cuba. CET has joined with the Trombone Shorty Foundation and the Havana Jazz Festival to organize “Getting Funky in Havana,” set for Jan. 14-18, 2020. The concert series will feature New Orleans groups Soul Rebels and Tank and the Bangas, together with current Cuban sensation Cimafunk.

“In general, the narrative about Cuba is not as sexy or optimistic,” Laverty concedes. “[But] When you look at a crowd that size, dancing, smiling, crying for five hours that’s pretty unique. You don’t get that too many places in the world. Artists understand that. Some want to make a political statement, some want to be part of change. A major pop star like a Bruno Mars or Beyonce would be breaking still fertile ground [in Cuba] in terms of PR value.”

He adds that different promoters and managers have recently reached out to him. “A lot of people still want to perform in Cuba they just don’t know how.”


Martinez concurs: “I think the list of artists who want to perform in Cuba is quite long,” says the attorney, who hinted that a concert by at least one of those artists could be announced soon.

“The Cuban people hadn’t had anything like those mega-concerts for many years,” says Darsi Fernandez, a representative of Spanish rights society SGAE in Havana and co-founder of the Cuban music magazine AM/PM, recalling that night in 2016 when the Rolling Stones played Havana. “So I think people feel like that was a special moment; it was something unique that happened during a special time. But of course they would be thrilled for it to happen again.”