Sheriff Frank Stiles
June 6, 1871, Woodbury County certified the proceedings to organize the County of Osceola. Cleghorn was the first town cite to be laid out in anticipation that the Sioux City & St. Paul Railroad Company would come through the town. Cleghorn was later rename to Sibley after General H. H. Sibley. There were only three townships to Osceola County in its inception. Running from east to west across the county: numbered 100 was Horton Township, numbered 99 was Holman Township, and numbered 98 was Goewey Township.
July 4, 1871, the people of Osceola County met not only to observe and recognize their Independence, but also to place nominations for candidates to fill the county offices at the first election to be held in October of 1871. No one knew each others qualifications, except that the men came from the same neighborhood in other parts of the country. The men to be nominated and elected were to hold a trial position, were to be weighed in the balance, and given the opportunity to prove their fitness, or to be found unworthy of the trust that was imposed in them. Jeff Cutshall, a local shoe cobbler in Sibley, was nominated for the position of Sheriff of Osceola County. About a hundred people gathered that day along with the nominated candidates.
In October of 1871, the settlers of Osceola County met to nominate their first County Sheriff and other elected officials. At the election there were no contentions of political parties and no regular opposition ticket except for independent candidates. Jeff Cutshall tied with the independent opponent, Frank Stiles, a general merchandiser in Sibley, which most people known him as "Old Stiles." Ties had to be decided by drawing lots, however, neither were present at the election. Delila Stiles, Frank's wife, was appointed Superintendent of Schools for Osceola County.
January 3, 1872, the Board of Supervisors appointed Frank Stiles the position of Osceola County Sheriff.
In 1872, St. Gilman was the 2nd town established in Osceola County. Like Cleghorn, the name was later changed to Ashton in 1882.
Otter Creek near St. Gilman, (Ashton), Iowa
Main Street, St. Gilman, (Ashton), Iowa
In March of 1872, Sibley was named the County seat for Osceola County.
In June of 1872, the Sioux City & St. Paul Railroad Company completed the line through Cleghorn (Sibley) and were visited by there first train shortly thereafter.
In July of 1872, the first term of District Court was recorded for Osceola County with the honorable Henry Ford presiding in Sibley, Iowa. The first case on the calendar was L. F. Diefendorf vs. J. H. Winspear and others. Diefendorf was attempting to restrain J. H. Winspear, Sheriff Frank Stiles and others from building school houses in out of the way locations. In September of 1872, Diefendorf withdrew the action and the school house construction continued. There were 95 rural schools throughout Osceola County at one point in time. Many of these school houses later became residences for friends of county officials that belonged to the "grafter gang."
July 18, 1872, the Board of Supervisors fixed the sheriff's salary at $200 per year.
August 12, 1872, the Board of Supervisors appointed Frank Stiles to survey the swamp lands of Osceola County, and his compensation was fixed at 10 cents an acre. The Board also made arrangement contracting the construction of Osceola County's first court house in the amount of $3,447 to Henry Phringston. The court house was to be completed by November 1, 1872. On October 21, 1872, Henry Phringston was contracted to receive an additional $1,053 to build a coal house, steps to the court house, one vane and flag staff, and to fit up room under the stairway. In all, the first Osceola County Court House would cost $4,500.
September 17, 1872, Frank Stiles purchased handcuffs and leg irons in the amount of $51.
September 27, 1872, the Board of Supervisors voted to divide Holman Township into two townships. Holman Township now encompassed section 99, range 42 and 41; section 99, range 40 and 39 was given the name of Ocheyedan Township. Until 1884, these two townships were referred to as East and West Ocheyedan.
October 7, 1872, the Board of Supervisors voted to divide Horton Township into three townships. Section 100, range 42 became Fenton Township; section 100, range 41 became Wilson Township; section 100, range 40 and 39 became Horton Township. Afterwards, by demand of the people in Fenton Township, the name was changed to Viola.
Frank Stiles was rumored to have belonged to a "grafter gang". Like many new counties organized at that time, grafters and looters would prey upon newly organized counties and loot the county treasuries. The gang would place nominations for county positions and then import fraudulent voters to secure the positions at the fall election. J. H. Winspear, an attorney and newly elected official to the Osceola County Board of Supervisors, was said to be the head of the gang. A committee of 27 men was appointed to get the resignation of the mendacious members of the Board of Supervisors. The first home the posy visited was J. H. Winspear; however, Winspear was forewarned and secured protection from Sheriff Stiles. The committee went to another officials home, but that man too was forewarned and not at home. Sheriff Stiles deputized several men and armed them in hopes to keeping the peace. These deputized men were on 24 hour call. On one occasion the deputized men were congregated at a saloon in Sibley and placed there firearms along one wall. John H. Douglass, known as a witty Scotsman, called a friend over and gave the man certain instructions to be followed. A few minutes later, the deputized posy heard the shouts of "Fire!" They all went hurrying out of the saloon to see what all the commotion was about. While they were gone, Douglass came in through the back door and gathered up all the firearms and dumped them through a trap door in the floor, which unknown to him at the time contained four feet of water. The Osceola County Treasury was looted of more than $22,000 in just a few months. A grand jury was held in the spring of 1872, presided my H. G. Doolittle. Indictments were later found against every county official who had participated in the looting. A bond of $100 was placed on each official responsible. The bond was placed in an effort to drive them out of the county and allow them to escape without further trouble. In all, Osceola County was left with a debt of about $40,000 under the leadership and plotting of J. H. Winspear. Stiles was not re-elected at the October 1872 election.
May 30, 1873 - Frank Stiles opens up a large and well selected stock of Dry Goods and Groceries at his new store on 9th Street in Sibley.
In 1914, Frank Stiles and his wife Delila were found dead in a hotel in North Dakota. They were asphyxiated.
One of the last homestead buildings in Osceola County,
built in 1871, one mile East of Sibley
A sod house in 1872