THE BLOG
09/25/2014 06:17 pm ET Updated Nov 25, 2014

It's Time to Talk About Cuba

I fell in love with Cuba at my grandparents' dining room table. I always sat on the far right hand corner, to the left of my grandfather, who always sat at the head. We ate every meal on turquoise placemats, and my grandfather always had oatmeal for breakfast.

My grandfather ate his oatmeal with prunes. And when he'd eat his oatmeal, he'd tell me about his days at the Justice Department. And when he told me about his days at the Justice Department, he'd tell me about the Cuban Missile Crisis and the Bay of Pigs.

My grandfather was the Assistant Attorney General of the Tax Division under Robert Kennedy. In 1962, Kennedy put him in charge of raising the $53 million that Fidel Castro demanded in exchange for the 1,179 exiles imprisoned in Cuba after the failed Bay of Pigs invasion.

He told the story best near the end. The Castro clock was ticking and my grandfather and his team were short $1 million. They told Bobby Kennedy that without that money, Castro would not make a deal so Kennedy got on the phone with the Archbishop of Boston.

"And the Catholic Church gave Bob the money," my grandfather would say, with a swift whip of his soft hand. "Just like that."

I knew it was his favorite part of the story.

But his other favorite part was during the Cuban Missile Crisis. My grandfather used to take walks with Bobby Kennedy along the mall. On one unusually balmy October day, Kennedy walked with his jacket over his shoulder, and as he looked up at the Washington Monument he said, "Imagine: this could all be gone."

I was eight years old and I knew more about the Kennedys and Cuba than I did about Disney.

But to me, Cuba was its own fairy tale.

I was a junior at New York University in the Fall of 2006. I wanted to be a poet and I wanted to be a journalist, and on one unusually gray October day, I spotted a highlighter blue flier on a bulletin board that said: Study Abroad in Havana, Cuba.

And so I did. Not without my grandfather's blessing, of course. All he wanted was for me to become a writer, (because our law school battle was over) and if living in Cuba was going to be the experience that made me a writer, all he had to say was, "Don't tell the Cubans that you know me."

And so I didn't. But I did get to know some of the Cubans. And I did get to know some of Cuba. I did walk along the Malécon late at night when the waves rise up and smash right over the wall and I did hear that Fidel Castro was dead.

But I also heard that he was alive.

When you fall in love, it's difficult to see your partner's flaws. When I fell in love with Cuba, I could not see the palm trees for the Sierra Maestra, even though history and journalism told me they were there. It wasn't until I went to graduate school, and developed a journalist's skeptical eye and ear that I knew where to look for the answers and how to ask the right questions.

And the right question is always, why.

Well then, why Cuba?

Because Cuba and the United States have not had a normal relationship since before my grandfather and Bobby Kennedy walked on Washington.

It's been over fifty years, and Castro and the embargo still stand.

But they won't always. Because in life, both leaders and grandfathers eventually die. And when they die, everything changes.

Cuba is on the cusp of that change. And ninety miles north, so are we.

Stay tuned for my blog about all things Cuba, and Cuba, if you're listening, it's about that time that we talk.