A small group of friends and I began a week-long Cuban adventure touring Old Havana in a 1952 Chevy Styleline convertible exactly nine years ago today. We had no idea we were visiting during what proved to be a very narrow window when Americans could travel to Cuba with relative ease under Obama-era rules (and it wasn’t that easy). I’ll never forget when our older Cuban taxi driver asked us, in broken English, “How could America elect Trump over Clinton?” Here we were, less than two months after the 2016 election, and a man who had spent most—if not all—of his life under Fidel Castro’s authoritarian rule was worried about America’s democracy. With my broken Spanish, all I could say back was, “Muy complicado.”