Spanish in the Caribbean Anglosphere provides a historical overview of the Spanish presence in the English-speaking Caribbean, showcasing reminders of enduring Spanish dominance that predate any semblance of English sovereignty in the region. The chapter charts the expansion of Spanish cultural hegemony and linguistic legacy, tracing the influence of the Spanish from Columbus’ encounters with Caribbean territories and indigenous peoples previously unknown to Europeans. It discusses the remnants of Spanish influence visible throughout the Caribbean through historical landmarks and place names. It explains how the legacy of both the Spanish and the English nearly did not materialise and the possibilities that could have ensued. This chapter seeks to navigate the controversies surrounding Europeans' exploration of lands previously unknown to them, focusing on the origins, impact, and both tangible and intangible legacies of the Spanish while highlighting the primary legacy as the Spanish language, the first foreign language of countries in the Caribbean Anglosphere.