This article presents a fictional dialogue between Cuban Minister of Education Ena Elsa Velazquez Cobiella and US Secretary of Education Betsy DeVos to provide a comparative snapshot of the ways Cuban socialist and US capitalist education systems tackle challenges to the teaching profession. Dr. Velazquez has invited Ms. DeVos to the popular beach resort town, Varadero, Cuba, to discuss education policy, teacher recruitment, and practice. Common challenges in both countries include low enrollment in teacher education programs, increases in alternative teacher certification options, and high teacher attrition. Their solutions differ: Ms. DeVos advocates for increased privatization through her support of charter schools and vouchers; Dr. Velazquez supports greater investment in public schools. Ms. DeVos favors decentralization and religious instruction in contrast to Dr. Velazquez's ardent preference for a centralized and fully public system. Themes of business influences, parental choice, local school control, and values emerge in their exchange.