The first female sheriff in the United States, Helen Stewart, was born in New Jersey in 1850 to Susan and James Garwood. By the time she was 20-years-old, the family lived in Scranton, Pennsylvania, where her father worked as a railroad superintendent and her and her mother worked as milliners.

Helen married Daniel P. Stewart at her home in Scranton on 11 January 1872. Daniel, born in 1838, was a railroad engineer from Albany, New York. The couple had four children and, by 1890, the family lived in Springfield.

Dan was elected sheriff of Greene County in November 1894. He only got to serve less than a year of his term; he died on July 23rd, 1895, possibly of peritonitis after complaining of “violent pain in the stomach” the previous Sunday. He died shortly after undergoing surgery. Dan was only 57-years-old.

Stewart’s death left the county without a sheriff. Dr. James Ormsbee, Greene County Coroner, served at interim sheriff, but several “prominent Republicans” proposed to nominate Stewart’s widow, Helen, to succeed her husband.

Several Republicans were in the running for sheriff, including former sheriff T.A.H. Grantham, although none of them were yet willing to announce their intention to seek the office until after “due respect had been paid” to Stewart. The Democrats also had a slate of candidates, including former sheriff F. M. Donnell. In the meantime, someone would be appointed to fill Stewart’s office before the election. Some thought it should be the deceased sheriff’s son, Dan Stewart, Jr. However, Dan Junior was only about 18-years-old and the legality of him being old enough to hold office was questionable. As for Helen Stewart, some Republicans pointed out that there was no state law “prohibiting a woman from holding office.”

On Friday afternoon, August 9, 1895, the county court appointed Dan Stewart’s widow to take over office until a special election could be held. With this, Helen C. Stewart became the first female sheriff in the United States. She took the oath of office at 2:20 p.m. and promptly reappointed all of the deputies Dan has appointed, except for Edmonson, who was ineligible because he was running for sheriff. Meanwhile, Democrats and Republicans were planning to select candidates for the upcoming special elections. The special election was held on September 10 and former Sheriff F. M. Donnell was elected.

By about 1910, Helen and most of her children had moved to Kansas City. It was there she died on April 30th, 1919, of burns received from a fire at her home. She was 70-years-old. She was returned to Springfield and buried with her husband at Maple Park Cemetery.