historian suggests that Jennings's financial situation may arisen from the expenses incurred during his political campaigns, his long-time service in state government, and being too busy to adequately manage his farm. Jennings and his wife frequently entertained visitors, legislators, and other dignitaries at their Corydon home. At a high-profile dinner in 1819, he hosted President James Monroe and General Andrew Jackson at a dinner held in their honor in Jeffersonville, when the two leaders were making a tour of the frontier states. In 1822 Jennings solicited a $1,000 personal loan from the Harmonists in a letter to his political ally, George Rapp, but his request was denied. Jennings was able to secure personal loans from friends by granting mortgages on his land. Earlier in his career as a land speculator at Vincennes, when land prices decreased significantly, he was forced to sell several tracts of land at a loss. By the late 1820s, Jennings was critically short of cash. He depended on income from political office to pay his expenses. His farm was not likely to provide sufficient financial support. Because the thirty-eight-year-old Jennings was prohibited by law from running for reelection to a third term as Indiana governor in 1823, he was forced to consider other political options. Jennings decided to return to Congress. Return to Congress In September 1822, shortly before his second term as governor expired, Jennings became a candidate for Congress after William Hendricks resigned his seat to run for Indiana governor. A special election was held on August 5, 1822, to fill Hendricks's vacant seat in Congress. At the same time, the state's increased population gave Indiana three congressional seats. A regular congressional election was held on the same day to elect three Indiana congressmen. Jennings and Davis Floyd were the principal candidates in the special election, which Jennings won. In the regular election to fill the seat for Indiana's Second Congressional District, Jennings easily won, defeating James Scott by a wide margin. Jennings became a Democratic-Republican to the 17th Congress and Lieutenant Governor Ratliff Boon succeeded him as governor. Hendricks ran unopposed and was subsequently elected as governor to succeed Boon. Jennings won reelection to Congress and represented Indiana's Second District until in 1830. He became a Jacksonian Republican in the 18th Congress, but switched his allegiance, becoming an Adams Republican in the 19th and 20th Congresses, and then aligned with the Anti-Jacksonians in