Attorney and "Jeopardy!" champ Paul Trifiletti said Greenlawn's Harborfields High School gave him the grounding in classical education that helped him win $106,801 on the quiz show last year and to compete this week on the TV series' Tournament of Champions.
"I really have a lot of respect for my high school and my high school teachers," said Trifiletti, 35, who was born on Long Island, raised in Centerport and is in the process of moving with his wife, Jennifer, to Boston from Georgia. "After my initial run on 'Jeopardy!,' I emailed Patricia Taylor, who teaches social studies and government history at Harborfields," the 2003 graduate told Newsday. "I let her know I was going to be on 'Jeopardy!' and asked her to watch and to circulate the email to the other teachers, thanking them for the quality of their teaching."
Trifiletti — a five-day champion in episodes that aired from March 4-6 and 10-11, 2020 — faced off against Jennifer Quail and Ryan Hemmel on Wednesday in the 2021 Tournament of Champions quarterfinal game 3. "Unfortunately, I ended up with only a hundred dollars at the end of the game," Trifiletti said. But he, like all the other defeated players, might possibly score a wild-card slot to stay in the tourney.
Tournament play, he learned, requires a different style than regular "Jeopardy!"
"The style of play is much more aggressive, in a good way," he said. "It's faster and I actually had to change my play strategy. I'm a very conservative player: I play from the top to the bottom, I march my way down the categories, I move to another category, I march my way down … very methodically, very logically. But in the TOC, usually the play is from the bottom up and people go hunting for Daily Doubles: 'Oh, look at the $1,200 clue, look at the $1,600 clue,' wham! Because if you hit a Daily Double in a category that you're strong in, you can take the lead and really do a number on your opponents."
Years before "Jeopardy!," Trifiletti competed in academic quiz bowl in high school — where as an incoming junior, he penned an Aug. 12, 2001, Newsday op-ed against stereotyped portrayals of Italian Americans in the media.
He went on to college at William & Mary and earned his law degree at Boston College. He began his legal career in the Boston area, then he worked as an assistant district attorney in Athens, Georgia, while his wife earned a doctorate there.
The elder of two siblings, Trifiletti credits parents Salvatore, a commercial banker, and Carmelina, a high school teacher in the Smithtown Central School District, for his lifelong love of learning. "My parents love knowledge and very much value education. And also it was growing up in a community of people who also value that kind of thing. A lot of the people I grew up with were very good, smart kids who've gone on to do really cool things. And being around folks like that encourages you, and you learn from that."
He also credits "growing up 40 miles from one of the most diverse and cultured cities in the world and the opportunities it gives you, like going to Carnegie Hall to see performances and going to The Metropolitan Museum of Art and the Museum of Natural History. All that kind of stuff really provides fertile ground."