Jebediah Obadiah Zachariah Jedediah Springfield is the purported historical founder of the town of Springfield. Springfield had many famous quotations, such as "A noble spirit embiggens the smallest man," and was well known for his silver tongue (literally; a metal prosthetic tongue, his original tongue having been bitten off by a Turkish pirate in a grog house fight).

Springfield led a band of wagons westward along with his partner Shelbyville Manhattan (They had misinterpreted a passage of the Bible and were looking for "New Sodom"); but they parted ways when Manhattan wanted to found a town where people could marry their cousins, and Springfield wanted a town devoted to: chastity, abstinence, a flavorless mush he called root-marm and where people would be free to worship how they wanted and "grow hemp for making ropes". Manhattan went on to found the rival town of Shelbyville. In the winter of 1807 Jebediah reportedly built Springfield's first hospital alone out of wood and mud.

On an expedition to Springfield's historic "Fort Springfield," Bart Simpson uncovered inconsistencies in the Jebediah legend. In "Lisa the Iconoclast," Lisa Simpson proved that "Jebediah Springfield" was a bloodthirsty pirate and enemy of George Washington named Hans Sprungfeld, who had changed his name in 1795 to hide his identity and who hated the town of Springfield. This was written on the historical "missing piece" of George Washington's portrait.

Springfield is said to have dramatically killed a bear with his bare hands. A statue of this sits in the center of the Springfield town square, in front of the city hall (the bear probably killed him). He is also said to have once tamed an untamable buffalo (although he later secretly admitted that it had already been tame; he merely shot it). The Springfield Marathon commemorates an occasion on which he ran across six states in order to avoid his creditors. In The Telltale Head, Bart beheaded the statue, thinking that this would make him more popular. In reality, the town became depressed and angry, leaving Bart to endure The Tell-Tale Heart - style guilt before replacing it.