Indiana Statehood
In 1816 Pennington was elected as a delegate to Indiana's first Constitutional Convention. As a slavery opponent, he was naturally in party with Jonathan Jennings. He and the other anti-slavery delegates had long since wanted to make Indiana permanently a "Free State". Pennington had encouraged Jennings to run for Congress against Harrison's candidate, and once there he further encouraged him to use his position to speed the territory's path to statehood. The hope was that upon statehood, the constitutional convention could be stacked against slavery, and then the state could elect its own governor rather than have it appointed by the President. They hoped that this would allow the state to be rid of any more pro-slavery governors. At the constitutional convention they did just that, slavery was clearly banned in the new constitution and the Governor was banned from holding any federal position.
Article 8, Section 1: But, as the holding any part of the human Creation in slavery, or involuntary servitude, can only originate in usurpation and tyranny, no alteration of this constitution shall ever take place so as to introduce slavery or involuntary servitude in this State, otherwise than for the punishment of crimes, whereof the party shall have been duly convicted.
Dennis Pennington ran for a seat in the senate of the new government. He won the election and became the first speaker of the Indiana State Senate from 1816–1818. He was an outspoken critic of slavery and a Whig during his tenure as a state representative. Pennington served in the Indiana State Senate from 1816–1820, 1825–1827, 1830–1833, and 1842–1845. Pennington also served in the Indiana House of Representatives 1822–1824, 1828–1830, and 1845–1846.
Ever the anti-slavery activist, in 1818, Pennington had three Kentuckians indicted for violating the state's "Man Stealing Act" when they forcibly took a black woman from a home in Harrison County and removed her to Kentucky. Governor Jennings requested that the Governor of Kentucky send the men to Indiana for trials; after several years of correspondence the governor of Kentucky refused on constitutional grounds. The incident caused governor Jennings to change his position on helping fugitive slaves escape and instead attempt to prevent them from entering the state.
In 1825, Pennington campaigned for the position of Lieutenant Governor, but he was defeated. Later he was appointed to be the Sheriff of Harrison County, and ran to election for a second term. During his election campaign his opponent claimed due to Pennington's infirmities of age he would be unable to fulfill the duties of the office. Pennington challenged him to a wrestling match so that younger man could prove his superiority; his opponent declined. Pennington won that election and served as sheriff for second term.
In the 1830s and 1840s Pennington was one of the most outspoken members of the General Assembly in opposition to the internal improvements plan. He was among the nine men, which included James Whitcomb, who voted against the Mammoth Internal Improvement Act. From the beginning, he railed against the majority; he claimed their plans, which would have no direct benefits for his constituency, would only bankrupt the state and would quickly become obsolete by the railroads. His predictions ended up being nearly correct. Every company started for internal improvements was bankrupt by 1840 and the state was only able to keep one canal out of all the projects and lost over ten million dollars, the equivalent of fifteen years of tax revenue, in the process. The final canal was taken by creditors in 1842, leaving the state with nothing for all the money it invested.
In his later years Pennington served for a decade on the Indiana University Board of Trustees. By the 1840s he was the oldest man in the General Assembly and was affectionately called "Uncle Dennis" and "Father Pennington". He died in his Harrison County home on September 2, 1854, aged 78, and was buried in the Pennington Chapel Cemetery.
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