The story of the historic Greenwood District is a bittersweet one that speaks of triumph but was interrupted by tragedy, leaving one wondering, "what if?" The Black people of Greenwood had managed to overcome oppression, segregation, and widespread racism, only for all their progress to come to a sudden halt in May 1921. The last breaths of May 2021 marked a hundred years since the Tulsa Race Massacre. The massacre was a two-day attack performed by weapon-carrying white men against the thriving Black community in the Greenwood district in Tulsa, Oklahoma. While the Tulsa Race Massacre was one of the worst racially motivated carnages in U.S. history, and it is essential to bring awareness and proper respect to it and events like it, the massacre will not be the focus of this book. This project chooses to focus on the positive parts of the Greenwood District history and shine a light on the achievements and stories of early 20th century Black Americans and the formation and eventual astounding prosperity of the Greenwood community.