Most people can only ever dream of competing on “Jeopardy!” At 19 years old, Caleb Richmond (SFS ’25) has already appeared on the show twice, so far accumulating total winnings of around $40,000 across both tournaments.

Richmond first competed in the “Jeopardy!” 2018 Teen Tournament as a sophomore in high school, advancing to the semifinals and walking away with $10,000 in prize money. The reunion tournament, which brings back contestants who competed in various teen tournaments, featured Richmond in an episode that aired March 2.

Twenty-seven students compete in the tournament, and in his first round, Richmond faced off against two other college students and won to now move onto the semifinals. The winner of the tournament will receive a grand prize of $100,000 and a place in the 2023 “Jeopardy!” Tournament of Champions, which will feature the most successful contestants from the show’s current season, all competing for a grand prize of $250,000.

Richmond said that while the competition itself is important, the highlight of his return to “Jeopardy!” was reuniting with the friends who he made during the high school tournament.

“I’m 19 now, and I’ve known these people since I was 15, and just getting to see them in person was what I was looking forward to the most,” Richmond told The Hoya. “Of course, everyone asks about the game and how that is, but really, what is most important to me is seeing the people.”

“Back then, it was all new, and we all kind of thought it was a once-in-a-lifetime opportunity. But this time, we were all so surprised that we were coming back,” Richmond added. “I think we just really took our time to take everything in, in a way that we didn’t get to the first time.”

Richmond said he views game strategy and trivia to prepare for the show.

“There’s an online archive of all of the old games, and I would look through and see what categories I was better at, what I was weaker at,” Richmond said. “Then I would take what I didn’t know, put it into a flashcard deck, and kind of go from there.”

Molly May (CAS ’24), Richmond’s close friend, said she enjoyed having a front row seat to Richmond’s development as a contestant. 

“It has been incredible to witness Caleb continue his Jeopardy career,” May wrote to The Hoya. “I’ve seen him grow so much in his knowledge and self-confidence throughout the process.”

May said her faith in Richmond’s abilities helped encourage him as he prepared for his appearance on the show.

“I’ve watched Caleb practice his trivia knowledge for hours on end, often by watching old Jeopardy episodes,” May wrote. “I knew he would be a great contestant on the show, but sometimes Caleb just needs that last boost of self-confidence.”

Claire Sattler — a senior at Yale University, winner of the 2018 Teen Tournament and current competitor in the 2023 High School Reunion Tournament — told The Hoya that participating in “Jeopardy!” has been the source of unlikely but meaningful relationships.

“I really cannot imagine my life without my ‘Jeopardy!’ friends, which is crazy considering that the things that brought us together was just these two whirlwind, random days in L.A. filming a TV game show when we were high school kids,” Sattler said.

Sattler said she and other contestants had not anticipated returning to the show.

“It felt like a weird homecoming, almost. Because we all really made peace with the fact that we were almost certainly never coming back,” Sattler said.

Sattler said time has brought Richmond and her closer to one another, as she has mentored him through his high school and college years.

“The friendship grew over the years,” Sattler said. “I’m two years older, and I think I definitely served somewhat of an older sister role in his life, which I’m really grateful that I got to do.”

On his part, Richmond said that, given the opportunity, he would love the chance to return to the show again in the future.

“If producers would like to have us back, I will come back instantly,” Richmond said. “I will come back right away.”