Coast Guard helicopter pilot Tim Keily (right) with Jeopardy! host Ken Jennings. Keily will compete in his first Jeopardy! show on Monday (5-27-24)

Alaska’s state tree is this alliterative spruce that shares its name with an Alaskan City. What is Sitka?

Questions about Sitka pop up from time to time on Jeopardy!, but contestants aren’t as common. Now, for possibly the first time, a Sitkan will compete on the long-running game show. 

Tim Keily is a Coast Guard helicopter pilot at Air Station Sitka. He grew up in Connecticut, watching Jeopardy! with his mom, but didn’t become a diehard viewer until recently.

“In the last five or six years, I think my wife and I have watched every single episode,” Keily said. “We usually have it on delay on a DVR, but we always catch up.” 

They’re trivia lovers, though Keily definitely has his category preferences. 

“I’m always excited when there’s a sports category, history, things like that,” Keily said. “When you start going into Shakespeare and heavy literature stuff, or there’s an opera category, that’s gonna scare me away pretty quick.”

Trivia aficionados have to jump through a few hoops to try their hands at the blue Jeopardy! board, starting with an online test that can be taken once a year. Keily took his first test in 2016, and never heard back. So he took it again. And again. Two years ago, a few months after he’d taken the test another time, he got an email with an invitation to take another test, this one filmed. Then a few months later he was invited to an interview. Then another seven or eight months went by…until all of a sudden it was go time. 

“And then back in March, I get the call and it was only about a month before taping,” Keily said. “It’s a lot of waiting, and then a lot of excitement at the very end.”

So he flew to Culver City, California to tape his first show.

“You know, when you first get the call, you think ‘Oh, man, I must be pretty smart.’ And you get there, and you realize everybody is really smart, and then you go through the game you’ve played a million times at home in your brain, but playing it live is way different,” Keily said.

He says the buzzer speed is what really separates the players. On Jeopardy!, you can’t buzz in and cut off the host before they’ve finished asking the question, and there’s a penalty if a player jumps the gun.

“If you ring in before that…everyone else gets a chance to buzz in before you. And if you if you wait too long to buzz in, somebody else knows the answer to that question on the stage with you probably,” Keily said. “And then there’s times where no one really buzzes in right away. That should be a clue for you to not buzz in either. That’s probably a really difficult question.”

Then on the other side of the podium, a Jeopardy legend Ken Jennings is asking the questions (or delivering the answers, rather). Jennings holds the record for the longest winning streak on Jeopardy!.

“He, personally, is one of the best players of all time, probably, at least among the very best Jeopardy! players of all time,” Keily said. “So you know, you’re meeting your idol as well as playing a game with him as the host.”

How he did on his first show is kept under wraps until it airs- no spoilers here. But Keily will be back in Sitka next Monday to relive the highs and lows with fellow helicopter pilots at the air station. 

“If you get a single question right, for that moment, you feel pretty darn good about yourself, you feel like you’re the smartest person in the country for a minute,” Keily said. “And then if you get one wrong, you feel the opposite pretty quickly, too. But, you know, don’t put too much stock in any one question,” Keily said.

“It was really just fun to be there,” he added. “A great experience.”

Sitkans who want to watch Kiley’s first Jeopardy! show can tune in to ABC at 6 p.m. on Monday, May 27.