The Riot Begins
Despite the pleas of several community leaders for the growing crowd to break up and go to their homes it continued to swell, raising additional concerns in Greenwood. Shortly after 10 PM, another larger group of armed blacks went to the courthouse to offer support to the sheriff, who again refused their assistance and asked them to go home. During this time someone demanded that another person give up his gun and was refused. This was followed by a gunshot, and the first shot was followed by an exchange of gunfire between the black and white groups.
Patrons leaving a nearby movie theater were caught in the crossfire. There were casualties among the contending crowds, but reports are conflicting as to how many. At least a dozen were killed between the two sides. The black group was heavily outnumbered and tried to withdraw to Greenwood but they were pursued by the white mob and by the local National Guard troops, who deployed in a manner to protect the surrounding white neighborhoods and took into custody blacks found outside the confines of the Greenwood neighborhood wherever they could.
The pursuing white mob looted stores and businesses as they entered the Greenwood area (and some white-owned businesses in the downtown district). By midnight another group of armed whites attempted to enter the courthouse but were turned back by the sheriff and his men. Meanwhile, sporadic gun battles continued around the fringes of the Greenwood area. Most of the gunfights occurred along the railroad tracks which marked the boundary of Greenwood. In several, all-night cafes and restaurants meetings were held to discuss activities once it became light.
Throughout the night and early morning gun battles continued. An arriving passenger train was hit with gunfire as it pulled into the station, but there were no injuries. Several groups of armed whites ignited homes and businesses on Archer Street in Greenwood, using rags and other combustibles thrown on roofs. Buildings were fired into what would today be called drive-by shootings, in many cases, gunfire was returned by the occupants. Shortly after midnight several of the businesses on Archer Street were ablaze, and when Tulsa firemen arrived they were held back at gunpoint by the arsonists.
The white mob continued to set businesses and some homes afire throughout the remaining hours of darkness, and many black families began trying to escape from Greenwood. Others joined in the multiple gun battles which at times nearly died out, only to flare up again. Throughout the early morning hours, the number of dead and injured continued to mount, on both sides of the conflict. A rumor began to spread among the white rioters that a train of armed black supporters would be arriving sometime during the following day.