Narcotics Inspector Bert S. Gregory died on October 25, 1922, from a gunshot wound the day after his weapon accidentally discharged. He was 53 years of age at the time of his death.

On the day he was shot, Inspector Gregory and another colleague were conducting surveillance on an informant who was to make a purchase of narcotics with marked money provided by the inspectors. Prior efforts to make the purchase had been unsuccessful, and the two inspectors decided that one of them would "shadow the informant" while the other would leave the area for a while in order to allay suspicions. Inspector Gregory decided to visit a nearby hospital where his colleague, Inspector A.M. Sheets, was recuperating from a wound he received when he and Inspector Gregory were ambushed by narcotics suspects a month earlier on September 28, 1922. While at the hospital, Inspector Gregory's gun fell and accidentally discharged, fatally wounding him. He died the following day.

Inspector Gregory's courage, general intelligence, and adaptability for law enforcement earned him an appointment under the Harrison Act. Previously he served as deputy sheriff of Iron County, Missouri, for several years and later was promoted to sheriff. His father and grandfather previously held this position, and Gregory served as sheriff from 1899 to 1903. In addition, Gregory also served as deputy sheriff of Madison County, Missouri, for approximately one year and the deputy county collector of Ironton, Missouri, from 1915 to 1917. After receiving an appointment under the Harrison Act, he entered duty as a deputy collector on January 1, 1918, and transferred to the Revenue Agent's Office as an internal revenue inspector on May 19, 1919.

Inspector Gregory was born in St. Louis, Missouri, and was survived by his wife, Mrs. Jessie Gregory. At the time of his death Gregory was assigned to the Kansas City Division of the U.S. Department of the Treasury, Bureau of Internal Revenue.