Regular Play[]
He made his Jeopardy! debut on October 11, 2021, and did what most fans considered impossible by defeating 38-time champion Matt Amodio. After defeating him, Jonathan went on to win 10 more games, netting $246,100 in the process. He achieved the records of highest-winning and longest streaking giant killer (term given to contestants who defeat ultrachampions, or people who have won 10 or more games), taking both records away from Emma Boettcher (3 games and $98,002 after defeating 32-time champion James Holzhauer). Jonathan’s run also made history in a different way - Matt and Jonathan are the only back-to-back superchampions in Jeopardy history.
| Game No. | Air Date | Final score | Cumulative Winnings | Notes |
|---|---|---|---|---|
| 1 | October 11, 2021 | $29,200 | $29,200 | First game with Michael Davis as executive producer. Jonathan's first game without a runaway and he ends Matt Amodio’s 38-day win streak, and also beat challenger Jessica Stephens by $401. Later, Jessica joined the ToC by winning Week 1 of the SCT. |
| 2 | October 12, 2021 | $22,500 | $51,700 | Jonathan becomes the second giant killer to win more than a single game after an upset of a superchampion. |
| 3 | October 13, 2021 | $18,300 | $70,000 | Jonathan's second game without a runaway. |
| 4 | October 14, 2021 | $24,000 | $94,000 | |
| 5 | October 15, 2021 | $23,700 | $117,700 | Seventh player to become a 5-time+ champion after defeating a 5-time+ champion. |
| 6 | October 18, 2021 | $25,200 | $142,900 | |
| 7 | October 19, 2021 | $13,200 | $156,100 | |
| 8 | October 20, 2021 | $37,700 | $193,800 | Jonathan's third game without a runaway. |
| 9 | October 21, 2021 | $22,100 | $215,900 | Jonathan's fourth game without a runaway |
| 10 | October 22, 2021 | $14,200 | $230,100 | First player to become a 5-time champion after unseating a long-standing champion. |
| 11 | October 25, 2021 | $16,000 | $246,100 | |
| 12 | October 26, 2021 | $18,400 | $248,100 | Jonathan's fifth game without a runaway. Nancy Donehower ends his streak. |
Tournament of Champions[]
In the second quarterfinal game, he faced 5-day champion Andrew He and 4-day champion Christine Whelchel. After Andrew lost a $10,000 Daily Double, Jonathan had a $6,000 lead going into Final Jeopardy. Final Jeopardy was a Triple Stumper, and Andrew wagered just small enough to be ahead of his on a cover bet; thus, Andrew advanced to the semifinals by $2, while he and Christine were knocked out in the first round of the Tournament.