Many of Greenwood's founders were descendants of people who had walked the Trail of Tears alongside the Five Civilized Tribes, or who had fled to Indian Territory seeking escape from the Deep South. After the Civil War, Muscogee Freedmen and Cherokee Freedmen gained citizenship in their respective nations. Others arrived during the Oklahoma land rushes of 1889 through 1891. In 1905, Booker T. Washington visited and encouraged residents to build on what he saw as extraordinary 'industrial capacity.' The following year, the community was formally organized as Greenwood. O.W. Gurley, a wealthy Black landowner from Arkansas who had resigned a presidential appointment under Grover Cleveland, purchased land designated to be 'only sold to colored,' setting the physical boundaries that defined the district. Jim Crow laws, perversely, helped insulate the community's economy by forcing Black residents to spend within their own neighborhood.

The massacre began when police accused a Black shoe shiner of assaulting a white woman. White Tulsans had grown resentful of Greenwood's prosperity and expanding boundaries. What followed was systematic destruction: an armed mob burned thirty-five blocks, reducing one of the most affluent African-American communities in the country to ash. Insurance claims were denied. Lawsuits were dismissed. For decades afterward, survivors rarely spoke of what had happened, fearing it could happen again. The silence was so effective that many Oklahomans grew up never learning about the massacre at all.

Within ten years of the massacre, surviving residents who chose to remain in Tulsa had rebuilt much of the district, accomplishing this despite active opposition from white political and business leaders and punitive rezoning laws designed to prevent reconstruction. By 1941, over 240 Black businesses operated in Greenwood. The district continued as a vital community until desegregation in the 1950s and 1960s ironically undermined it. Once Black residents could live and shop elsewhere, Greenwood lost much of its captive economic base. The construction of the I-244 expressway further fractured the neighborhood, a wound some residents consider as damaging as the massacre itself.

The work of remembrance has been slow and contested. A commission established in 1996 recommended full reparations for descendants of massacre victims, but resolution has remained elusive. The Greenwood Cultural Center, dedicated in 1995, anchors preservation efforts, while the Greenwood Rising History Center opened in 2021 at the corner of Greenwood Avenue and Archer Street. John Hope Franklin Reconciliation Park, named for the distinguished historian whose father B.C. Franklin was a Greenwood attorney, was dedicated in 2008 as a space for education and reflection. In 2021, President Biden visited the Greenwood Cultural Center during the 100-year commemoration. In 2022, the Greenwood Historic District was added to the National Register of Historic Places, and in 2023 a Senate bill proposed designating it a National Monument. The ground beneath Greenwood holds layers of meaning: ambition, destruction, resilience, and the ongoing question of what America owes when it burns down what its citizens built.