As Indiana's first executive, Governor Jonathan Jennings deserves, perhaps, a consideration that we cannot give to his successors in the gubernatorial office. Jennings came from Pennsylvania to Indiana Territory in 1806, settling first at Jeffersonville, then at Vincennes, where he was admitted to the bar and began the practice of law in 1807. The "practice," however, seems to have been little more than nominal, as he drifted into clerical work in connection with the territorial Legislature, and this employment turned him in the direction of politics. His first appearance in the political field was as a candidate for the office of Territorial Delegate to Congress in 1809. The issue on which the campaign was waged was that of admitting slavery into the territory, and Jennings, as the anti-slavery candidate, was elected after a bitter contest. During the rest of the territorial period he remained in Congress, as he was returned in 1811 and 1813, and this fact, doubtless, contributed greatly to the antislavery movement, which in 1816 succeeded in bring in Indiana free. It was Jennings who laid before Congress the memorial asking for an act to enable the Territory to become a State, and with the passing of that act and the subsequent Constitutional Convention, he was chosen President of that body, being also a delegate from Clark County. In the subsequent campaign for State Officers he ran for Governor against Thomas Posey, the Territorial Governor, and won by a large majority.

Of his peculiar task as the first Governor one of his biographers (Woolen) says: "The making and putting into motion of the machinery of a new State requires ability of a high order. Revenue is to be created, laws for the protection of life and property to be drawn and passed, and divers other things to be done that the foundations of the government may be properly laid. The Governor proved himself equal to the task." It must be said that this latter laudation is not too strongly put. Jennings was one of the commissioners who, at the Treaty of St. Mary's, Ohio, secured from the Indians the large tract of territory, covering the central part of Indiana, afterward known as the "New Purchase," and in 1820 he personally accompanied the commissioners who had been appointed to select a site for the permanent capital. In 1822 he was elected a representative to Congress and resigned the governorship to accept that office, the remainder of his term being filled out by Ratliff Boon. He remained in Congress eight years, then, being defeated in the race for another term, retired to private life. His one other public service was as a commissioner, in 1832, to treat with the Indians for lands in northern Indiana and southern Michigan. He died July 26, 1834, at his home about three miles west of Charlestown, and lies buried at the Charlestown Cemetery, where, for many years, he grave lay neglected and unmarked, though it now has a fitting granite monument.

In appreciation of Jennings written by John H. B. Nowland, who knew him personally, he is described as a man of great personal magnetism, freehanded, generous of nature and kind of heart, with much simplicity of character. During his service in Congress, Mr. Nowland says, "No letter was ever addressed to him on the most trivial, as well as important matter, that was not promptly answered and his business attended to;" and the biographer further adds that the honest discharge of every official duty entrusted to him won for him wide esteem.

Throughout his political career, Jennings had his bitter enemies, who were unescapable then as now, but many of the fulminations against him are at this day their own condemnation. For example, Waller Taylor, a pro-slavery opponent of territorial days, tried to provoke him to a quarrel and a duel for no particular reason except political ones, and disgustedly dubbed him a coward because he persisted in being amiable and friendly. In 1816, Elihu Stout, editor of "The Western Sun," and a coterie of Harrison supporters, raged because he was back of a (to them) nefarious scheme to introduce a rival newspaper, "The Centinel," in Vincennes. The humor of this did not seem to strike them.

According to Mr. Nowland, Governor Jennings salary of $1,000 per year was paid in treasury notes worth about $600, and his expenditures more than doubling this depreciated salary, left him involved in debts, which he never got free from.