Host Alex Trebek joked he was running out of things to ask Jennings during the portion of the show when contestants reveal some personal information.
"You can now call me Alex, by the way," Trebek quipped in introducing Jennings for Monday's show.
Jennings, a software engineer, bested Lori Fountain, a substitute teacher from Henderson, Nev., and Michael Magdalena, a government analyst from Anaheim, Calif., who won, $101 and $1, respectively.
None of the contestants gave the correct question to the final answer: "'I am the rose of Sharon' and 'When you know your name, you should hang on to it' are from two different books titled this."
The correct question: "What is 'The Song of Solomon?'"
Jennings went into the final round with $28,000 and wagered $7,000.
Trebek noted Jennings has broken all show records except for single-day total winnings. The record stands at $52,000.