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House Staffer Keeps ‘Em Guessing on ‘Jeopardy!’

(Courtesy Will Anderson)
(Courtesy Will Anderson)

Quiz show junkie and Capitol Hill staffer Will Anderson raked in more than $23,000 in winnings and garnered comparisons to defending Super Bowl quarterback Russell Wilson for engineering an astonishing, come-from-behind victory during his three-day run on “Jeopardy!” What else would you expect from a trivia buff who claims his mother still has home movies of him blurting answers out at the TV while growing up?

“It’s a blast being a ‘Jeopardy!’ champion,” the legislative aide to Georgia Democratic Rep. David Scott told HOH about cobbling back-to-back wins early last week. Anderson, who said he finally got the call to come in for a live taping in November — “I’ve taken the online test probably every year that they’ve had it,” he said — sailed through his first appearance, but hit a rough patch on night two.  


His saving grace? Going all-in (save for $1) on the nail-biter final round.  

His knowledge of confections allowed him to keep the crown for a second day. Things weren’t so sweet the following evening. After running the table on Jan. 21 (ending the day $19,000 in the black) and outmaneuvering the other contestants Jan. 22 to collect a $4,199 payday, the wheels finally came off on Jan. 23. Anderson maintained a solid lead through the first two rounds, scoring a quick $200 in the “Government Jobs” category (he nailed “parole officer”), then racking up dough by correctly identifying “MTV Unplugged,” “steeple,” “tiara,” “assessor,” “city manager,” “chief of staff” (a White House question), “sergeant-at-arms” (House procedural question), “spreadsheet,” “pedigree,” “Addis Ababa,” “Bangkok” and “Howard Hughes.”  

The Double Jeopardy round was more trying, with Anderson losing the lead by misfiring on “Edmonton Oilers.” He attempted to stay in it, whizzing through a number of TV shows in translation (“Dancing with the Stars,” “Game of Thrones” and “Everybody Loves Raymond” were all money in the bank). But blanking in Final Jeopardy — Who knows how long “What is the St. Lawrence River?” will haunt his dreams? — forced him to retire with $99. A tragic end. But what a ride. “Just being on set was the fulfillment of a childhood dream,” he said.  

Anderson, who got his start on Capitol Hill in the employ of Georgia Democratic Rep. John Lewis, recounted childhood evenings spent enthralled by game show drama. “My mom and I would watch ‘Wheel [of Fortune]’ and ‘Jeopardy!’ while making dinner when I was a kid. So, I’ve been a fan for nearly 25 years,” he estimated.  

Anderson said he attempted to try out for the show in 2009 during an open contestant call held at Montgomery College, but failed to calculate how many others wound up having the exact same idea. “It turned out to be a larger crowd of ‘Jeopardy!’ fans than I think they anticipated. So, we wound up tailgating in the parking lot instead,” he said. The trivia night devotee apparently makes the rounds all over town. “My usual is Wednesday nights at The Pinch in Columbia Heights,” he said of the weekly hangout that hosted the watch party for his first appearance alongside quintessential quizmaster Alex Trebek.  

(Courtesy Will Anderson)
(Courtesy Will Anderson)

But Anderson said he’s no stranger to the intellectual bouts hosted by Looking Glass Lounge , DC Reynolds , RFD , Penn Social and Acre 121 .  

The newly minted TV star was still mulling how to spread around the financial windfall, but seemed to be leaning toward a balanced approach of debt reduction, retirement savings and perhaps one splurge: some new wheels. “I’ve been wanting to bike the C&O trail up towards Pittsburgh,” the avid cyclist said.  

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