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San Juan is at the heart of many important contributions Puerto Rico has made to American history and culture, including in the areas of art, sports, music and cuisine. Craig Martin and Earl Bridges explore Puerto Rico’s Old City (Viejo San Juan) and the vibrancy of the artists who live there. Sculptor Ana Rosa Rivera talks about using art to enhance the lives of its poorest residents. Together with her husband Charles Juhász-Alvarado, they all tour Contrafuertes, a museum in the heart of Viejo San Juan that is a collaborative artists-driven place. Artist Freddy Mercado exhibits large costumes that represent gender identity, ageing and independence. Freddy and LGBTQ rights activist/filmmaker Carla Cavina collaborated on a film telling the story of spirituality, physical suffering and identity called “Fractura.” Carla explains why art and expression through film helps people struggling with their own personal identity. Earl and Craig also tour Charles and Ana Rosa’s art studio and learn about struggle within the longest running colony in history. The issues are messy and not clean cut, but art often presents what is broken in society in a way that doesn’t necessarily provide a solution to the brokenness. For many on the island, political independence will still require positive interaction and collaboration with the United States. Most Puerto Ricans have tight bonds with family members living in the US and breaking those bonds isn’t part of the equation.