Jesse Matheny is a customer success specialist originally from Huntington, Indiana.
| Game No. | Air Date | Final Score | Cumulative Winnings | Notes |
|---|---|---|---|---|
| 1 | April 26, 2021 | $2,600 | $2,600 | Jesse's first win from third place. |
| 2 | April 27, 2021 | $0 | $3,600 | Eric Anderson ends his streak. |
Champions Wildcard[]
In the fifth quarterfinal game, he faced 2-day champions Emma Hill Kepron and Patrick Curran. He gave eighteen right responses (including one DD) and no wrong responses. Although Emma was the only player correct in Final after crossing out Jane Eyre, he made a small wager and advanced to the semifinals.
In the third semifinal game, he faced 1-day champion Kat Jepson and 2-day champion Alex Gordon. He gave twenty correct responses (including two DDs) and two wrong responses (including one DD after finding all of them). He was the only player correct in Final and advanced to the finals.
In the finals, he faced 1-day champion Deb Bilodeau and 2-day champion Mira Hayward. In day one, he gave nineteen right responses (including two DDs) and one wrong response (the DD after finding all of them). He and Mira got Final wrong and he wagered $2,600. In day two, he gave seventeen right responses (including one DD) and no wrong responses. Final Jeopardy was a Triple Stumper. He went big, and finished with $50,000 as first runner-up.