Pulaski County covers approximately 432 square miles of North Central Indiana. The county seat is the town of Winamac. Four other incorporated towns (Francesville, Medaryville, Monterey and Star City) and several unincorporated villages are also located within the County. About 13,400 residents currently live in this mostly rural county.

Established in May 1839, Pulaski County is named after Count Casimir Pulaski. A Polish national, Count Casimir Pulaski distinguished himself in the American Revolution holding the rank of General in Washington's revolutionary cavalry. The Count's first assignment for the Revolutionary Army was as commander of the elite 30 troop bodyguard for General Washington. He was then given the task of reorganizing and training the cavalry. Once the reorganization was completed he was given command of that portion of the army. Later in the war, this distinguished military leader was killed while in command of his troops during the siege of Savannah in 1779.

During the organizational phase of the county, George P. Terry was appointed as the first sheriff. A native of New York State, George Terry settled into Pulaski County during a time period when very few white settlers lived within its borders. He served in the post only during the organizational phase of the County, serving from April through October 1839. Mr. Terry went on to hold other positions of county office and was the Justice of the Peace when he died on March 25, 1848.

In October of 1839 the county held its first election. David Clinger was elected to replace George Terry. David Clinger, the first elected sheriff, retained his position as Sheriff until August of 1844. Newspaper articles from that time utilize the spelling of the last name starting with a C. However in most later articles the reader will find the last name of the Sheriff using the letter "K", David Klinger.

Phillip Dellinger became Sheriff in September of 1897 and served two terms. During his second term an act of the State Legislature extended his term to January 1, 1901. Since that time period all Sheriff's in Indiana have taken office on January 1st, after their election.

In 1907 Sheriff Charles Oglesby became the first county officer to be killed in the line of duty. He was shot and killed while attempting to arrest three men stealing a ride on a Pennsylvania Railroad freight train. One of the three men also died of injuries he received during the event. In the early morning hours of October 5, 1907, Sheriff Oglesby was requested to assist the engineer removing three hobo's from the train. The engineer had found them during a stop in Star City and ordered them off, but they refused. Unbeknownst to the sheriff, the three men were not hobo's but actually a gang of safe crakers who had recently burglarized the Marsh store in Burnettsville, Indiana. At the approach of Sheriff Oglesby, one of the three men, later identified as John Smith, ran from the train, up the railroad tracks north from Pearl Street in Winamac. The other two, Patrick Shea and Frank Webb, stood their ground. Both men fired shots at Sheriff Oglesby and the sheriff returned fire. Frank Webb was the next to run from the scene and was hit below the left shoulder by one of the Sheriff's bullets as he climbed a fence. Patrick Shea again fired at the Sheriff, this time hitting him in the chest. However, before he could escape cleanly, Patrick Shea was shot in the abdominal area by the sheriff.

Sheriff Oglesby was taken to his home where he died several hours later, in the company of his family. A posse was quickly deputized and set out after the bandits. Shea and Webb were found in a corn field just north of Winamac. Both were wounded and could run no more. They surrendered without incident. Once the two were brought back into town, a crowd had gathered and the suggestion was made that there should be a lynching. The deputies ordered the crowd to disperse and then transported the two wounded men to Logansport to see after their wounds. Not long after, John Smith was captured along the railroad tracks north of town. He was not brought back to town, but instead transported to the Starke County Jail. This was for the safety of the prisoner and because there was no jail in Pulaski County at the time.

Patrick Shea died a few days later from the wounds received from the gunfight. Frank Webb was convicted of Murder in the Second Degree and given a life sentence which was served at the state prison in Michigan City. There were no records found of a court case against John Smith who was reported several blocks away from incident when it occurred. He was however, convicted of the burglary of the Burnettsville Marsh store and sentenced, along with Frank Webb, to 10 to 20 years for that crime.

Tragedy once again touched the Sheriff's Office in October of 1967. Sheriff Milo Lewis was shot and killed by a prisoner who escaped from the Pulaski County Jail. The prisoner, Arthur James Lewis, was furnished a gun by his girlfriend who smuggled it into him during visitation. Arthur Lewis was later recaptured, tried and convicted for the murder of the Sheriff.

Sheriff Bayne Ward died in office in 1983 and was replaced by his wife Charlotte Ward. She was appointed to replace him and then won the next election for a term of Sheriff. Charlotte Ward is, to date, the only female Sheriff in the history of this county.

In September of 1956, $82,000 was appropriated for a new jail. Sheriff Ralph Galbreath was the first sheriff to occupy that facility, moving his family in at the end of September 1958. A sheriff lived in the jail until 1979 when Sheriff George Riley is believed to be the last Sheriff to live, with his family, in the Pulaski County Jail. However, that facility was utilized by the Sheriff's Office until the current facility was completed in 1997.

In July of 1996 the current facility housing the Sheriff's Office, Jail and the Superior Court was started under the supervision of Sheriff Carl Freeman. This 56,400 square foot building was completed at a construction cost of 7.2 million dollars. Also included is a modern, computer aided, dispatch center with Enhanced - 911 systems that service the entire county. The jail can accommodate 120 inmates.