Did you know that Abraham Lincoln was the U.S. president who deemed Thanksgiving a national holiday? Luckily, Derek Lombardi M.C.P. ‘17 did; he stumbled on this fun fact cramming for his appearance on Jeopardy! this past June— one of three “Slumdog Millionaire moments” that inched the urban planner precariously close to unseating the nine-time winner, a lawyer from Memphis.
Lombardi’s path to the podium—and to his regional planning career—both got their start at the University of Maryland. During his graduate degree in urban studies and planning he was a fixture at both the National Center for Smart Growth and Looney’s Pub trivia nights, a popular haunt for his cohort after evening classes.
After graduation, he took a job with the Delaware Valley Regional Planning Commission, where he has led several projects that inform long-range plans for the Philadelphia area, including their efforts for the National Zoning Atlas project; Lombardi has personally combed through the zoning codes of nearly 120 municipalities to help guide smarter, more sustainable growth in the region, including housing, infrastructure and transportation. When not at the office, Lombardi continued to dabble in weekly trivia nights in downtown Philly and went as far as applying to the show several times without luck.
He finally scored an audition last year. In March, just minutes before he was set to give a presentation for work on sustainability, Lombardi received a phone call from an unknown number inviting him to come to Los Angeles for a taping. Suddenly, achieving a lifelong dream would merely require sacrificing some PTO.
“I got the call exactly 364 days after my audition date, which I think is just one day shy of having to start [the audition process] over,” he said. “And I had such a busy spring, but what was I going to say? No? I just studied every free moment I had.”
Four weeks later, he was lobbing answers in the form of a question (and trying not to fall off the dizzying platform stage), going head-to-head against the reigning champion and a law student from Toronto. His parents, twin brother and a horde of L.A.-based cousins cheered him on from the live studio audience.
While Lombardi didn’t prevail, the experience was a total win: More than the second-place prize money, there was an unexpected outpouring of support and community that followed.
“I’ve gotten contacted by people I haven't heard from in a long time; it's been sort of amazing,” he said. “It’s a good reminder of your village and the people that care about you.”
Below, we get behind his Jeopardy! experience, naturally in an answer-and-question format:
This mechanical tool helped Lombardi get “buzzer ready” weeks before airtime: What is a ballpoint pen? Once Lombardi was selected, the prep began, which included standing in his living room poised with a ballpoint pen to simulate game play (buzzer synchronization is one of the biggest hurdles for contestants). It’s one of several tactics Lombardi undertook in the four weeks leading up to the show, which also included a Google doc “study guide” and turning to the internet for priority topics, like geography and presidents—which literally paid off for Lombardi. “I almost skipped over Lincoln, because everyone knows him,” he said. “So I couldn’t believe when it came up on screen. It was like they had checked my browser history before writing the clues.”
This cardigan-wearing personality is as “Midwestern nice” as advertised: Who is Ken Jennings? Unlike his notoriously aloof predecessor, the effusive Jennings is a “super nice and a super fun guy,” said Lombardi. During rehearsals, he welcomed the contestants into the Jeopardy! alumni community and shared how big a deal it was that they had gotten this far. “I obviously never met Trebek but there was a sense of ‘I’m the host, you’re the nerds,’” said Lombardi. “You can tell that [Ken] is genuinely interested in what we have to say. He told us how proud he was of us and was just excited for us to be there.”
Daily Double: A high school earworm helped Lombardi nail this high-value, hip-hop answer: What is Doo Wop (That Thing)? “My friends were obsessed with Lauryn Hill,” he said. It was one of several questions seemingly made for Lombardi, a pop culture nut, including others on rage bait, a penguin meme, the Amazon show Jury Duty and “GeoGuessr,” which he played with work colleagues during COVID. “I kept thinking, ‘How is this a category?’” he said.
This classmate of Lombardi’s—and longtime quiz bowl wingman—preceded him on Jeopardy!, winning the Teen Tournament of Champions in high school: Who is Raynell Cooper M.C.P. ‘17? Lombardi learned of Cooper’s claim to fame during their first meeting at student orientation. They became fast friends, both taking graduate assistantships at the Department of Housing and Community Development and regularly attending—and crushing—Looney’s Trivia Night. Their winnings, always in gift card form, covered their $3.00 Bud Lights and to-go salads for the next day’s lunch. “Raynell is a pistol, and has been my go-to on Jeopardy! since the MCP program,” said Lombardi. “Knowing him gave me the confidence to continue to apply.”
These famous surveyors marked the end of the line for Lombardi's run at first place: Who are Mason and Dixon? While the final clue, “partnerships,” proved to be a challenge for Lombardi, the roughly 60 seconds leading up to it were worse. His second-place position, arguably the hardest place to be in Jeopardy!, required “five-digit math in both directions” in a very close race for first. “I just panicked and wrote a number down, and people online have been saying it's one of the worst wagers they've ever seen,” Lombardi laughed. He offered a wild guess to the clue about British astronomers; the correct answer, he says, still haunts him. “I'm just like, dang, the Pennsylvania-Maryland guy couldn't get that one,” he said. “There’s a historical marker sign [for the Mason-Dixon line] about a mile from my house.”
Beyond the $3,000 in winnings, Lombardi’s Jeopardy! experience led to this unexpected windfall: What is ‘his people’? With his family spread across the country, Lombardi says he sometimes feels like an island living in his transplanted home of Philadelphia. But his Jeopardy! appearance led to a tsunami of outreach. It was his most-liked post on Instagram. Closer to the air date, a friend offered up her backyard for the watch party; nearly 60 people showed up to cheer and boo through the broadcast. “I was tearing up a bit because I couldn’t believe how many people were invested in my performance,” he said. “It was just so cool seeing all of these people caring.”