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Born in Cuba and raised in the United States from age 6, Obejas moved to Chicago in 1979. For ten years she worked for the Chicago Tribune as a reporter on arts and culture, and received a Pulitzer for a Tribune Team investigation, as well as the Studs Terkel Journalism Prize. She covered such important historical events as Pope John Paul II's visit to Cuba in 1998, the arrival of Al-Qaeda prisoners at Guantanamo Bay, and the AIDS epidemic. A prolific writer, Obejas is also known for her creative work, which includes novels, short stories, and poetry. Among her fiction is the collection of short stories, We Came All The Way From Cuba So You Could Dress Like This? (1994), and the novels Memory Mambo (1996) and Days of Awe (2001). She has won two Lambda Literary awards for her work. Obejas uses her writing to reflect on her multiple identities as Cuban, lesbian, activist, and writer. Since 2006, she has been Writer-In-Residence at DePaul University, where she holds the Sor Juana Ines de la Cruz Chair. She also has a blog on current events for Chicago Public Radio.