Jeopardy champion James Holzhauer squares off against aspiring financial planner. Guess what happened?

As Jeopardy contestant James Holzhauer closes in on becoming the winningest contestant in the TV show’s 35-year history, one aspiring financial planner offers an inside perspective on squaring off against the best player many fans of the show have ever seen.

Monica Foy, who like most of the contestants that have gone up against the professional sports gambler who has changed the way the trivia game is played, finished a distant second behind Mr. Holzhauer. But because the show’s taping schedule is several weeks ahead of the nightly telecasts, Ms. Foy said she entered her match oblivious to the history that was being made by Mr. Holzhauer.

“I was nervous and was hoping I would be going up against somebody with a three- or five-day winning streak, so there wouldn’t be so much pressure on me to feel I had to win,” she said of her “stage fright” leading up to her March 6 contest, which was aired this past Monday.

“I remember asking another contestant the day before my taping if anyone had a winning streak going, and he just shook his head and said, ‘You’ll see,’” she said. “None of his shows had started airing yet, so we were blind-sided.”

Ms. Foy, 59, who is in the process of transitioning from a career in information technology to earning her Certified Financial Planner designation, was one of two challengers facing Mr. Holzhauer on Monday’s show after the reigning champ had already won 27 consecutive games and amassed more than $2 million in winnings.

Through Wednesday, Mr. Holzhauer, 35, had pushed his 30-game total winnings to $2,323,971, bringing him less than $200,000 from the show’s record winnings set in 2003 by Ken Jennings.

One significant difference between Mr. Holzhauer and Mr. Jennings is that it took Mr. Jennings 74 games to reach his record total winnings.

Ms. Foy, a longtime fan of the show, applied online for a chance to compete after years of hearing friends and family tell her what a great “armchair” player she was.

“When you’re there live on the show, it’s not like ‘armchair Jeopardy’ when you just blurt out the answer in your living room,” she said.

In live action, Ms. Foy said contestants are not allowed to click their signaling devices until after host Alex Trebek has finished reading the question, which introduces the stress of being quick enough to be first, but also knowing the correct answer.

Ms. Foy said Mr. Holzhauer, who is averaging just under $80,000 worth of winnings per show, plays the game show like a true gambler with big bets on the Daily Doubles and aggressive play from the first clue.

“He’s obviously very smart, and a talented poker player,” she said. “He’s fast off the buzzer and he’s fearless.”

One of Mr. Holzhauer’s trademark strategies is to start selecting clues from the bottom of the board, where the values are higher and the questions are more difficult. He also frequently wagers everything he has on the Daily Doubles.

The advantage of moving around the board, instead of working down a specific category from top to bottom, is that it can rattle your opponents, Ms. Foy said.

Like many of the games involving Mr. Holzhauer, Ms. Foy and her fellow challenger were confronted with a runaway situation by the time it got to the single clue of Final Jeopardy, which means they didn’t have enough to beat Mr. Holzhauer even if they bet all their winnings.

With $6,600 to wager, Ms. Foy nearly doubled her money by getting the final question correct.

Mr. Holzhauer, meanwhile, who entered Final Jeopardy with more than $72,000, also got the final clue correct, pushing his daily winnings to $130,000 for a solid 30-minutes’ worth of work.

“Once I saw him in action, I realized he’s going to go on for a long time,” Ms. Foy said.

Related Topics: Certified Financial Planner Board Of Standards Inc. (CFP Board)