By the time of his death at the young age of 50, Jennings had suffered political defeat, debt and health problems caused by years of alcohol abuse. He was buried in an unmarked grave and forgotten by history until the 1893 Legislature arranged for a tombstone.
“He was so instrumental in Indiana's statehood,” says Bill Brockman, former manager of the Corydon Capitol State Historic Site. Most memorable, says Brockman, was his rivalry with Harrison, the Indiana territorial governor and military hero who oversaw much of Indiana's progression toward statehood. The two had different views of what Indiana should become.
“Harrison was generally pro-slavery and anti-statehood while Jennings was just the opposite,” Brockman explains. “Jennings' faction won out and changed the course of Indiana's future.”
Harrison's popularity as a military hero put him in position to become president of the United States in 1841 (albeit for 31 days) while Jennings'
alcoholism cost him his career. By 1831, “the once premier Hoosier politician ... found himself without a public office,” wrote his biographer Randy Mills.
Historians consider Jennings Indiana's first professional politician. Although he owned a farm, his income came from government service from the time he moved to Indiana from Pennsylvania in 1806 to his last unsuccessful run for Congress.
While living in Vincennes, Jennings found work as a clerk in a federal land office and planned career moves. He soon realized options were limited in the Harrison-dominated capital, so he moved to Jeffersonville where more citizens shared his political views.
In his first campaign for territorial delegate to Congress, his supporters attacked the Harrison faction as aristocratic and pro-slavery. The latter was a fair charge because of the territory's Indentured Servant Act, which essentially legalized slavery by permitting contracts with servants that exceeded their life expectancy. The message resonated with voters.
“The 1809 Indiana territorial election for congressional representative featured one of the biggest political upsets in the region's history,” says Mills. Jennings defeated Harrison's choice: Thomas Randolph, “a thirty-eight-year-old Virginian of great refinement.” Jennings was 25.
For the next two decades, Jennings enjoyed spectacular success. He was re-elected territorial delegate in 1811, 1812 and 1814, and he presided over the 1816 convention that drafted the state's first constitution. Jennings was elected governor in 1816, handily defeating incumbent Territorial Gov. Thomas Posey. He was re-elected to the governor's office and then spent four terms in the U.S. House.
Jennings lost his seat in Congress in 1830 no doubt because he could no longer hide the effects of alcoholism. In Mills' book, the story is told of two passersby who spotted a drunken Jennings leaning against a tree in Charlestown. Overhearing one explain that he was a former governor, Jennings said, “Yes, a pretty governor. He can't govern himself.”
Jennings died a pauper in 1834 and was buried on his former farm. Almost 60 years later, the Indiana General Assembly appropriated $500 for a modest headstone, and his body was exhumed and moved to Charlestown Cemetery.