With Rutter out of the running, he used his space on the board to write an appreciative note to Trebek. Jennings, who is usually comfortable in literature categories, responded correctly.
Since Holzhauer’s strong second game put him in position to win the match if he got the response right, Jennings’s wager was as conservative as could be: $0. But Holzhauer produced the name of a character in the wrong Shakespeare play, handing the victory to Jennings.
With the win, Jennings took home a $1 million prize. Holzhauer, 35, who won one match, and Rutter, 41, who won none and was largely outbuzzed and outguessed by his opponents, each received $250,000.
Jennings came in with a reputation for unmatched endurance: He won 74 games in a row in 2004 and, in the years since, no contestant has come close to that streak. After his extraordinary run, he was able fund a career as an author, writing books on topics like trivia and comedy. He’d pop his head back in to the world of “Jeopardy!” every so often to participate in a tournament and line his pockets even more.
When Holzhauer first appeared on the show last year and began winning by margins rarely seen before, fans speculated on how his big-betting strategy would match up to Jennings’s game play. When the “greatest of all time” tournament was announced, there was no question that in order to win, Jennings would have to bet as big as Holzhauer, who won 32 games during his streak and holds the top 16 spots for single-game winnings. The most he won in one game, $131,127, is more than $50,000 greater than the record that stood before he showed up in April.
Jennings’s seasoned trivia chops combined with a riskier betting strategy turned out to be a lethal combination. In the four matches, he found eight Daily Doubles, bet all of his points on seven of them and got seven right.