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Jennings encountered financial problems, a situation exacerbated by his inability to keep up with his business interests and run the state government simultaneously. Ineligible for another term as Indiana governor under the state constitution, Jennings looked for other means of financial support. Shortly before completion of his second term as governor in 1822, Jennings was elected to the U.S. House of Representatives, before retiring from public service in 1831. In Congress Jennings promoted federal spending on internal improvements.

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