Soledad O’Brien’s first visit to Cuba was in 1998, when she covered Pope John Paul II’s historic trip there for NBC News.
She’s been back many times since, but this time she won’t be covering the event, but moderating separate panels with President Obama and First Lady Michelle Obama on their historic visit.
The White House tapped O’Brien, whose family’s roots are in Cuba, to moderate two events: First, a morning panel on Monday with the first lady with Cuban teenage girls, some of whom have studied in the United States. The students also will take questions submitted by American students to Discovery Education. Later in the day, O’Brien will moderate a panel with President Obama and entrepreneurs, in which Americans who have started their own business will share advice to their Cuban counterparts.
O’Brien started her own media company, Starfish Media Group, in 2013, after a tenure at CNN and NBC News.
O’Brien says that this trip will be “really interesting, especially since I am not covering it as a news reporter. I will be there as an entrepreneur.”
She said that she travels to Cuba every two years to visit family. Her mother grew up in poverty and left Cuba in the 1950s, before Fidel Castro came to power.
“She used to say that under Batista, he would do more than kill you. He would make sure that your family didn’t have any food,” O’Brien said.
Her mother finally got to return with O’Brien on a trip to Cuba about 10 years ago.
She thought “it was great to be back,” O’Brien says of her mother, now in her 80s. But “it was very emotionally challenging.” Many of her relatives had passed away as Cuba was isolated from the U.S.
This trip, O’Brien is bringing her 15-year-old and 14-year-old daughters and 11-year-old twin boys, the first time they will be there to meet their relatives and get a sense of what life is like for Cuban teenagers.
When Obama announced in December, 2014 that the U.S. would restore full diplomatic relations with Cuba, O’Brien wrote in an op-ed for CNN.com, “I had grown up rootless, disconnected from our family, unable to see firsthand what my mother’s country had become. The politics of the embargo alarmed me on both sides, even though I had no dog in that fight. The poverty astounded me, the restrictions, how people suffered a universal lack of opportunity. Yet I longed to remove the mystery surrounding the place and people my mother left behind. Now, perhaps, I can.”
The boycott, she wrote, was “punishing” for the Cuban people. She says that she is hopeful that the new engagement will expand the ties between the two countries, and that the U.S. can play a role in leading by example.
She says that when it comes to free speech, “I think that clearly in Cuba it is going to be a process.” When it comes to a free press, “I hope we are able to show the value of that.”