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By 1904, the Populist Party had disbanded. In 1908, Bailey was elected to a single term as a Democrat to the office of Winn Parish [[sheriff]]. In 1913, after his tenure as sheriff, Bailey began a 20-year stint as vice president and then president<ref name=bailey/> of the Bank of Winnfield.<ref name=lahist/> He worked to establish the Northwest Louisiana Game and Fish Preserve. He obtained state legislative funds to build a dam on Saline Lake near the boundary of Winn and [[Natchitoches, Louisiana|Natchitoches]] parishes. Bailey worked for improved roads and was partly instrumental in securing the wide city streets of Winnfield. He was influential in removing livestock from municipal streets.<ref name=bailey/>​
 
By 1904, the Populist Party had disbanded. In 1908, Bailey was elected to a single term as a Democrat to the office of Winn Parish [[sheriff]]. In 1913, after his tenure as sheriff, Bailey began a 20-year stint as vice president and then president<ref name=bailey/> of the Bank of Winnfield.<ref name=lahist/> He worked to establish the Northwest Louisiana Game and Fish Preserve. He obtained state legislative funds to build a dam on Saline Lake near the boundary of Winn and [[Natchitoches, Louisiana|Natchitoches]] parishes. Bailey worked for improved roads and was partly instrumental in securing the wide city streets of Winnfield. He was influential in removing livestock from municipal streets.<ref name=bailey/>​
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Bailey was a member of the [[Methodist]] Church and the Masonic lodge. He and his wife, the former Penelope Dickerson (1872-1961), are interred at the Winnfield City Cemetery. Mrs. Bailey died only  twenty-two days after the passing of her husband. There is no indication of any children.<ref name=cemeteryrecords/>​
 
Bailey was a member of the [[Methodist]] Church and the Masonic lodge. He and his wife, the former Penelope Dickerson (1872-1961), are interred at the Winnfield City Cemetery. Mrs. Bailey died only  twenty-two days after the passing of her husband. There is no indication of any children.<ref name=cemeteryrecords/>​
  
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