Jeopardy! Champion Greg Monson Stages Dramatic Comeback With Back-to-Back Daily Doubles

Greg Monson turned a challenging start into a winning performance on Jeopardy! after landing two consecutive Daily Doubles in Double Jeopardy! The videographer from Portland, Oregon, added $22,600 to his winnings and secured a second straight victory, bringing his two-day total to $31,300.

After surviving a clue-filled game on October 8, Monson returned on October 9 to face two new challengers: Dan Perkey, a brewer originally from Pittsburgh, Pennsylvania, and Kendra Kendell, a payroll analyst originally from Aurora, Colorado. This time, the competition took a dramatic turn as Monson used two well-timed wagers to regain control of the game.

A Yacht Rock-Themed Round Gets the Game Underway

The opening round celebrated Yacht Rock, with categories inspired by songs associated with the soft-rock genre. Contestants faced titles including “Africa,” “This is ‘It’,” “Sailing,” “I’d Really Love to See You Tonight,” “What a Fool Believes” and “Yacht Rock.”

Monson opened with a $1,000 clue in the “Yacht Rock” category. The question asked players to identify the Doobie Brothers member whose smooth vocals on “You Belong to Me” helped make the song a classic example of the genre.

Perkey buzzed in first and correctly named Michael McDonald, earning the first points of the game.

Monson soon encountered a setback when he uncovered the first Daily Double in the “Africa” category for $800. The clue referred to a part of the Sahara that extends eastward into Egypt. He wagered $1,000 but incorrectly responded, “What is the Sudanese Sahara?” The correct answer was the Libyan Desert, leaving Monson in negative territory early in the contest.

By the end of the first round, Perkey had established a comfortable lead with $5,400. Monson sat in second place with $1,800, while Kendell was at -$1,200.

Kendra Kendell Begins Her Comeback

Double Jeopardy! gave Kendell an opportunity to recover from her difficult opening round. In the “A Look at Historical Americans” category, a $400 visual clue showed a woman described as having been just 23 when she was escorted from the world.

Kendell correctly identified Bonnie Parker, one half of the infamous criminal duo Bonnie and Clyde, and began rebuilding her score.

However, the biggest shift in momentum came from Monson, who discovered both Daily Doubles in Double Jeopardy! on the round’s 14th and 15th clues.

Two Consecutive Daily Doubles Change Everything

The first opportunity appeared in the “Mammals” category, with a clue worth $1,600. It asked contestants to identify the largest cat native to the New World, whose name is said to derive from an Indigenous word meaning “he who kills with one leap.”

Monson wagered $4,000 and correctly answered “What is a jaguar?” The successful response gave him a significant boost.

He then found the final Daily Double in the “Journalism” category. The $1,200 clue referred to the original title, “Report of the Office of the Sec. of Defense Vietnam Task Force,” under which documents were published in several newspapers in 1971.

Monson correctly identified the documents as the Pentagon Papers and added another $4,000 to his score.

The back-to-back successes gave him an $8,000 boost and dramatically altered the standings. After falling behind early, Monson had regained control of the game, while Kendell had also made progress toward a stronger finish.

Final Jeopardy! Tests Knowledge of Bestselling Books

The final round featured the category “1990s Nonfiction Bestsellers.” The clue read: “This word began the titles of 2 bestsellers from the same man, one of the books is set in Alaska, the other in Nepal.”

All three contestants answered correctly with “Into,” referring to Jon Krakauer’s books Into the Wild, published in 1996, and Into Thin Air, published in 1997.

Perkey wagered $9,000, finishing with $18,000. Kendell risked $10,400 and ended the game with $20,800.

Monson wagered $9,000, bringing his final score to $22,600. He finished just $200 short of a runaway game but still had enough to claim the victory.

Greg Monson Secures His Second Consecutive Win

Monson’s latest victory was a striking turnaround from his early struggles. After missing the first Daily Double and ending the opening round behind Perkey, he capitalized on two consecutive opportunities in Double Jeopardy! to transform the contest.

His $22,600 win brought his two-day total to $31,300, allowing him to retain the champion’s title and prepare for another appearance on Monday.

With two victories secured, Monson will return to Jeopardy! looking to extend his winning streak against another pair of challengers.

Jeopardy! airs weekdays; check local listings. Episodes are available to stream the following day on Hulu and Peacock.