In September 2005, not long after Hurricane Katrina, I attended Jubilee South‘s second global assembly, held in Havana, Cuba. I was able to wander Havana streets and take in a small piece of people’s daily lives. I grooved in a jam session with a young rapper who had tattooed “Che” on his forearm, who skillfully dropped a rhyme of solidarity for Katrina survivors. I visited a hospital that trained doctors who served the poor in Haiti and Oakland, California. I witnessed gay couples openly holding hands during dinner at a neighborhood restaurant. I conversed with a taxi driver, who expressed great disappointment in the lack of shared prosperity in his country, but was even warier of US ambitions for the island country. This was not the picture painted by the US media or by Castro sympathizers. That is why I’m happy to hear that this week, President Obama will be challenged to lift the United States’ fifty-year embargo of Cuba at the Summit of the Americas in Trinidad. The US needs to be pushed. But so does Cuba. The stalemate between the failed capitalist and the failed communist states must be broken, at the very least for the sake of all of the people it has harmed. Obama’s lifting of rules that prevented families from visiting and sending remittances to Cuba is a good first step. Perhaps the resulting binding of familial ties between US and Cuban citizens will also create a space for improved relations between the countries. Space that could enable us to learn from each other’s tainted legacies and ask very different questions of each other like: How do you create safety net that ensures quality health, education and decent retirement for everyone? How do we protect your people from the worst of a storm? How can 21st century leaders collectively turn away state-sanctioned terrorism and the silencing of dissidents, and turn toward embracing true liberty and freedoms in words and deeds. This week in Trinidad, President Obama has the opportunity to take the next step toward this vision. Let’s hope that he seizes it.