This chapter chronicles Yirrande Valdez's perilous quest for asylum from Cuba, revealing the distressing realities faced by him and his family under an oppressive regime. It starkly contrasts the hope of gaining protection in the U.S. with the challenges and injustices embedded within the asylum process, including arbitrary detentions and biased judicial decisions. Through Valdez's story, the chapter underscores the broader systemic flaws that affect many asylum seekers within the American immigration system.