Until 1899 there had been ten independent streetcar operating companies in St. Louis, providing regular transit service in the fourth-largest city in the United States.

Whitaker fired his 3,300 workers summarily and was soon running streetcars only with the help of the St. Louis Metropolitan Police Department, who had volunteered up to a thousand men for that duty.

On the first day of the strike, May 9, the St. Louis Republic reported a full page of riot conditions across the entire city: multiple bystanders shot, an attempted lynching, a crowded streetcar being stoned by a mob sympathetic to the strikers, and policemen assaulted with thrown bricks and bottles.

The Police Board swore in 2,500 citizens in a posse comitatus commanded by a local realty agent, John H. Cavender, who had played a similar paramilitary role in the bloody 1877 Saint Louis general strike.

For their part the strikers made three unsuccessful attempts to dynamite the housing for the temporary workers in the car barns at Easton and Prairie Avenues.