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Loula Williams ran a popular theater and candy store in the Greenwood section of Tulsa, Okla., during the 1910s, making her one of the most prominent businesswomen in the neighborhood.

Williams Dreamland Theatre was doing so well that she started two other theaters near Tulsa, according to newspaper accounts and Charles Christopher, her great-grandson. Together, the three formed the Dreamland Theatrical Co.

Ms. Williams bought insurance for her businesses—though like some in the neighborhood, she was only able to patch together partial coverage through several policies. Even that did her no good when white mobs destroyed Williams Dreamland Theatre, along with most of Greenwood, during the city’s race massacre in 1921.

Ms. Williams suffered an estimated $79,164 in losses, according to lawsuits she later filed, equivalent to $1.2 million today. The three insurance companies to which she paid premiums denied her claims.

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