Jennings's Washington D.C. boarding room fell on his head, severely injuring him, and ill health limited his ability to visit his constituents, but he continued to remain a popular politician in Indiana. In the congressional election of 1826, Jennings ran unopposed. He won reelection in 1828, soundly defeating his opponent, Indiana's lieutenant governor, John H. Thompson. Jennings did not publicly favor a presidential candidate and won the Second District seat with support from voters who favored Jackson and Adams. During Jennings's final term in office House journals show that he introduced no legislation, was frequently not present to vote on matters, and only once delivered a speech. Jennings's friends, led by Senator John Tipton, took note of his situation and took action to block Jennings's reelection bid when his drinking became a political liability. John Carr, anti-Jackson man, opposed Jennings in a six-way race for the congressional seat and won the election. Tipton had arranged for others to enter the race and divide Jennings's supporters. Jennings left office on March 3, 1831. Later years Jennings was twice-elected Grand Master of the Indiana Grand Lodge of Freemasons, serving in 1824 and 1825. He declined reelection in 1825. Retirement Jennings retired with his wife, Clarissa, to his home in Charlestown. Tipton may have felt it had been mistake to force Jennings out of public service and hoped that work would force him to give up alcohol. In 1831 Tipton secured Jennings an appointment to negotiate a treaty with native tribes in northern Indiana. Jennings attended the negotiations of the Treaty of Tippecanoe, but the delegation failed in their attempt. Afterwards, Jennings returned to his farm, where his health steadily declined. He continued drinking alcohol, spending considerable time at a local tavern, and was frequently discovered sleeping in streets or in roadside ditches. Jenning's alcoholism worsened to the point where he was no longer able to tend his farm. Without a steady income, Jennings's creditors began moving to seize his estate. In 1832 Tipton acquired the mortgage on Jennings's farm and enlisted the help of a local financier, James Lanier, to acquire the debts on Jennings's other holdings. Tipton allowed Jennings to remain on his mortgaged farm for the remainder of Jennings's life and encouraged Lanier to grant the same permission. Jennings died of a heart attack, most likely brought on by another bout with jaundice, on July 26, 1834, at his farm