This answer might change soon, as James Holzhauer is on his way to topping the all-time record for Jeopardy! winnings. As of May 29, 2019, the records for Jeopardy! winnings are as follows:
Several important notes: Rutter appeared on the show in 2000 and won five games, at which point his streak ended due to the game show’s win limit, a rule that was lifted in 2003.
Second, Holzhauer, a professional gambler from Las Vegas, Nevada, seems poised to threaten Jennings' all-time streak; Holzhauer won his 30th consecutive match on May 29, 2019, adding to his running total for an astounding $2,323,971.
Holzhauer’s bold approach makes him an especially formidable Jeopardy! player. He attacks the bottom of the board to build up a bankroll, he told NPR, then purposely targets answer squares that are likely to contain a Daily Double, where he bets enormous amounts of money.
Previous winners have taken a more conservative approach. Ken Jennings' average Daily Double wager was $3,134, while Holzhauer bets an average of $9,266. He’s similarly confident during Final Jeopardy, betting $29,167 on average (Jennings’ average bet was a relatively paltry $7,665).
"[Holtzhauer has] gotten a lot of attention for his big wagers,” Rutter told The New York Post. “But if you don’t have the goods, it’s not going to do much for you.”
Time will tell whether Holzhauer can set the all-time record, but he’s clearly the most substantial threat to Jennings' legacy in recent memory.
He was never tied. The next person has way less Jeopardy winnings
They are not paid right away and must wait until after the program has aired
Jesse Cuevas, originally from Kansas, won for the 2nd day, adding $27,600 to his winnings.
Only the player who wins keeps their winnings. The second place contestant gets $2,000, and the third place contestant gets $1,000. On the Art Fleming versions, all players kept their winnings regardless of outcome, which was changed on the current version of the show to only the first place contestant doing so.
Eureka Nutt, a paralegal from Canoga Park, California (whose 1-day cash winnings total $18,801)
When you watch the show they show you what they get. Wheel of Fortune is not Jeopardy. You keep your winnings and if you don.t have any they give you $1,000.
Sarah Curtis, a mechanical and electrical drafter from Oceanside, California (whose 1-day cash winnings total $14,000)
Dan McShane, a baseball game logger from West Islip, New York (whose 1-day cash winnings total $18,801)
Justin Sausville, an urologist from Baltimore, Maryland (whose 2-day cash winnings total $58,401) won again
The winner keeps what he/she has won, the second place finisher receives $2000 and the third place finisher receives $1000. When the defending champion does not win a match, he/she gets to keep what he/she won in previous games, as well as the consolation prize for second or third place for that match.
Of the three contestants, the one who finishes with the most money wins the game and gets to keep the money. The contestant who finishes in second place receives $2000 and the third place finisher receives $1000. The winner of the show gets to return to play two new challengers. If the returning champion wins, that day's winnings are added to his previous winnings. If he finishes in second place, he receives $2000 for that game in addition to his previous winnings, if he finishes in third place, he receives $1000 plus previous winnings.
The winner keeps the winnings and comes back to play again. Second place pays $2000 and third $1000