October, 1872, Viola Township was organized and held its first election in John H. Douglass' shanty. John was then elected Sheriff of Osceola County.
In the fall of 1872, the first courthouse for Osceola County was constructed for approximately $5,000. The 36x36x20 foot tall building housed the Osceola County Sheriff's Office on the 2nd floor. The room was 11x20 feet and was lighted by three windows.
In 1873, the total population of Osceola County was 1,409.
January 7, 1873, the Sheriff's pay was amended to $16.65 at the end of each month ($199.80 per year) for serving Osceola County. Also on that date, Sheriff Douglass notified the Board of Supervisors that he appointed Charles M. Bailey as Deputy Sheriff.
In 1873, Charles Brannock, who lived near Ocheyedan, was like most of the settlers, hard up for something to eat, had caught some kind of an animal, probably a muskrat and after skinning it, was cooking the carcass on a fire outdoors. In an unfortunate moment the prairie grass soon caught fire, and soon the fire was spreading in every direction. Brannock was arrested and bound over. He was allowed to remain at home to get bail, but the next day the fury of the people demanded his incarceration and Sheriff Douglass was ordered out with the necessary papers. In order that the arrest should be a complete success, quite an army volunteered to go along and did on horseback, armed with Winchesters, so that their going presented quite a body of cavalry. They soon reached Brannock’s cabin and the terrified fellow was ordered to surrender which he did. He asked leave, however, to go inside and change clothes and once in, crawled out of the back window and by cautiously creeping at first and getting in the grass he made his escape. There were some who understood his condition of poverty and his peaceful and law-abiding disposition and who felt that while the act was a violation of the law, still it was not malicious nor intended; these wanted him to get away and we suspect that Douglass was one of them. They waited for his return in changed suit, and when sufficient time has elapsed, an investigation was made and it was found that he had escaped. Some one, a friend of Brannock, said that he just saw him going over the hill towards the south, and way went the cavalry flying after him; when the hill was reached the friend said he saw him going over the next one, and on went the horsemen in furious following, and thus for several miles they were led, and this with searching took up about the whole day. In the mean time, Brannock had started north while the searchers were still searching, he was safe in Minnesota, as only a few miles travel was required to get there.
February 21, 1873, The Board of Supervisors approved to increase Sheriff Douglass' monthly compensation an extra $33.35, making Douglass' salary $50 per month ($600 per year) for serving as Sheriff of Osceola County.
October 14, 1873, John Douglass was re-elected Sheriff of Osceola County, receiving 394 votes.
November 7, 1873, Sibley was visited by fire. The fire started in the rear of Barber & Lawrence's drug store located on 10th Street. The cause of the fire was either from a stove in the back part of the building or by an incendiary. Six local business' sustained the following losses:
Barber & Lawrence Drug Store $900 A. H. Clark Groceries $600 H. C. Kellogg Store $1,200 Kelley & Walrath Dry Goods $1,244 J. A. Cole Drug Store $2,000 Wilbern Bros. Stock $1,100 Total Damage $7,044
The fire was a hard blow on Sibley, but most of the businesses rebuilt on 9th Street.
February 20, 1874, Douglass' pay was adjusted to $40 per month ($480 per year) for serving as Sheriff of Osceola County.
July 4, 1874, Charles M. Bailey, formally a Deputy Sheriff of Osceola County, was appointed Marshal for the City of Sibley.
October 12, 1875, John Douglass was re-elected Sheriff of Osceola County.
January 4, 1876, Charles C. Ogan was appointed Deputy Sheriff of Osceola County.
In 1876, the Board of Supervisors approved the construction of the 1st Osceola County Jail. The building was 16x24x10 feet tall. The Osceola County Jail was built in the Courthouse yard.
October 3, 1877, William L. Harding, Governor of Iowa from 1917-1921, was born in a sod house in Osceola County. He was the son of O. B. and Emeline Harding. In 1890, O.B. Harding built a house which still stands on Section 2 of Goewey Township to this day.
October 9, 1877, John Douglass
was re-elected Sheriff of Osceola County over his running mates M.
Churchill and Jacob B. Lent.
October 14, 1879, John Douglass was re-elected Sheriff of Osceola County over his running mates Albert Romey, S.S. Parker, and Charles Bailey. Jacob B. Lent was appointed Deputy Sheriff of Osceola County.
In 1881, the members of the Board of Supervisors was increased from three to five.
In 1881, a three story building known as the Sibley Opera House was built. The building housed a furniture store, dances, traveling shows, school plays, graduations, and meetings. In the late 1960's the top two stories to the building was removed and currently the remaining building houses the Pizza Ranch.
John H. Douglass served one, one year term and four, two year terms as Sheriff of Osceola County from 1873 to 1882.
John H. Douglass served an additional two, two year terms as Sheriff of Osceola County from 1888 to 1892.
During his time as Sheriff, Douglass earned a lot of money but spent it all as fast as he earned it. He was known to be generous to a fault and had the reputation of being one of the best criminal officers in the state of Iowa. Douglass was engaged with the Iowa Land Company as a Superintendent for Osceola County. Douglass went to great lengths in protecting the interests of the homesteaders against agents who attempted to enforce collection of debts, which made him very popular. He held no political party and always ran as an independent candidate. He called himself "Mugwump."
In 1862, John H. Douglass enlisted in the US Army as a drummer, and then later served as a Corporal in Company K, of the First Iowa Calvary until the close of the war.