Jonathan Jennings - Later Years - Return To Congress

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Jennings continued to promote internal infrastructure improvement in Congress and used the issue as a platform for the remainder of his time there. He won reelection four times and became a Jacksonian Republican in the 18th Congress. He switched his allegiance becoming an Adams Republican in the 19th and 20th Congresses. He then aligned with the Anti-Jacksonians in the 21st Congress. During his terms, he introduced legislation to build more forts in the northwest, to grant federal funding for improvement projects in Indiana and Ohio, and led the debate in support of granting federal funds to build the nations longest canal, Wabash and Erie Canal, through Indiana. After the contested election of President Andrew Jackson in 1824 the House of Representatives decided the election, and Jennings voted with the majority giving Jackson the presidency. He served twice as Grand Master of the Indiana Grand Lodge of Freemasons during the later 1820s. In 1824, William Henry Harrison returned to Indiana to stump for the Adams Presidential candidate and Jennings and Harrison found themselves on the same side. The two men toured the state together, endorsing John Quincy Adams. They also gave speeches where they indicated their past political feud was over. In 1825 Jennings was a candidate in the Indiana General Assembly for the United States Senate. On the first ballot he came in second, and on the second ballot he came in third, losing the vote in the General Assembly to incumbent governor William Hendricks.

Jennings’ wife died in 1826 after a protected illness; the couple had no children. Jennings was deeply saddened by her loss and began to drink liquor more heavily. In a letter to his sister he also noted that he was afflicted with severe rheumatism. While drinking in 1828, an accident occurred in which plaster from the ceiling of his Washington D.C. boarding room fell upon his head, severely injuring him and preventing him from attending Congress for nearly a month. Later that year he remarried to Clarissa Barbee, but his drinking condition only worsened and he was frequently inebriated. In his final term in office, the House journals show that he introduced no legislation, was frequently not present to vote on matters, and only once delivered a speech. His friends took note of his situation, and a group led by Senator John Tipton decided to attempt to block his 1830 reelection bid. Tipton enlisted the help of war hero John Carr to oppose Jennings in the election while also arranging for other popular Anti-Jackson men to enter the race and divide Jennings' supporters. Tipton hoped that the need to work would force Jennings to give up his heavy drinking. Carr defeated Jennings, who left office on March 3, 1831.