In Cuba, street marches have historically been government-orchestrated events or dissident protests that are swiftly crushed by the authorities. So it was downright startling when, in May 2007, Fidel Castro’s niece sauntered down the street with a small army of drag queens waving gay pride flags.

Long before the Obama administration announced a dramatic shift in Cuba policy on Wednesday, asserting that isolating the island had failed, a couple of Western governments with close ties to the United States saw the potential to help gay Cubans, even though it meant working with a prominent member of the Castro family. Havana’s first observance of the International Day Against Homophobia and Transphobia marked the beginning of a remarkable evolution of gay rights in the most populous country in the Caribbean, a region where hostile attitudes toward sexual minorities remain the norm.

Mariela Castro, the daughter of the current president, Raúl Castro, has led the charge on legislative and societal changes that have given rise to an increasingly visible and empowered community. In the process, she has carved out a rare space for civil society in an authoritarian country where grass-roots movements rarely succeed. Some Western diplomats in Havana have seen the progress on gay rights as a potential blueprint for expansion of other personal freedoms in one of the most oppressed societies on earth.