In June 2018, Jennings won the $1 million prize in the Best of All Time quiz contest. His total earnings from the show are now estimated to be $4 million. In May 2016, H&R Block assessed that Jennings owed the company $1.04 million in taxes. Before his winning streak on Jeopardy!, Jennings worked as a software engineer at CHG Healthcare Services. According to Forbes, his net worth in 2022 is expected to be about $3.6 million.
His success as a game show contestant has boosted his net worth and he has a total asset of $4 million. He won $2,520,700 in 2004. In 2005, he won $500,000 and in 2011, he won $300,000 in the IBM Challenge. In addition to his fame as a game show host, Jennings is a successful writer and podcaster. His height and weight are listed as 5 ft. 10 inches and 185 kilograms.
Jennings has been married to Mindy since the early 2000s and has two children, Dylan and Caitlin. He lives in Seattle. His interests include reading comic books and writing quizzes about literature and mythology. He has also been an employee of CHG Healthcare Companies in Holladay, Utah. The show has earned Jennings a total net worth of $4 million as of 2022.