How a Freedom Trail tour guide ended up on ‘Jeopardy!’
When you see Sean McShane on “Jeopardy!” March 6, he won’t be wearing his work uniform.
“I’m one of the guys you see in Boston Common in the tricorn hats and breeches,” the Southie resident said in a recent phone interview.
Talking to the 2019 Boston College grad (“I really broke the mold with that one: BC guy moves to Southie. Call me a trailblazer.”) feels like talking to a standup comic who happens to be good at trivia. Which is basically his job, he says, as a costumed tour guide on Boston’s Freedom Trail.
The job is “a weird combo of teaching a history class and stand-up comedy. You have to keep people entertained and roll with the punches, because you’ll get people who walk by and heckle: ‘There’s Redcoats afoot!’ I never know what to say to that.”
A three-day winner in December 2022 who won $80,401, McShane is now part of a field of 27 contestants in “Jeopardy!’s” Tournament of Champions, which runs through at least March
14. The first contestant to win three games scores $250,000 and a spot on the upcoming “Jeopardy! Masters” primetime event on ABC.
“Jeopardy!” nerds like me will be tuning in to see how this super-bracket plays out — especially as it’s the first tournament of champs to include a “Celebrity Jeopardy!” winner: actor/comedian/writer Ike Barinholtz plays March
4.
Aside from McShane, two others have New England ties, according to show info: Jake DeArruda, originally from Ludlow, Vt., competed Feb. 28. Brown University sophomore Justin Bolsen — the show’s first-ever “Jeopardy!” High School Reunion Tournament Champion — competes March 5.
I caught up with McShane — who will watch his episode at Southie’s Woody’s L Street Tavern — to talk about his Long Island fiasco, the WBZ video that shocked him, and embracing Southie.
Q. How did you first land on “Jeopardy!”?
A. I have a group of friends; we go to the L Street Tavern to watch “Jeopardy!,” our Monday night ritual. They’d been telling me for months, “You should take the test!” I was like, “I’m going to, I’m going to.” Which is Seanspeak for: I’m not going to.
Then one night [they were pushing] so I took the test. That was January 2022. In September, I got a call: “Hi, Sean, this is Corina from ‘Jeopardy!’” I sat up in my chair. She goes: “Are there any dates in the next two months that wouldn’t work for you?” I was like, “No, no, I’m wide open!” Then she goes: “OK, bye.”
I was like: What was that? Five days later, I get a text: “Can you come out October 24 to tape?” I was freaking out.
Q. How did you find out that you qualified for this tournament?
A. Out of the blue, the week of Thanksgiving, I get an email from a guy at WBZ, the CBS affiliate. He said they’re doing a piece on the Wildcard Tournament and wanted to speak to a past local contestant. I go in. It’s all the stockstandard questions: “Were you nervous?” ”What do you do with the money?” Then at the end, they tell me they actually have a message from “Jeopardy!” They play a video. It’s Ken Jennings. He says, “I’m sorry to tell you we will not be able to invite you back for the Champions Wildcard competition.” I’m like, “OK, this seems kind of meanspirited.”
Then he goes, “Because you’re going straight to the Tournament of Champions!” My reaction was genuine shock. I never saw it coming.
Q. So you moved here in 2015 to attend Boston College. How long have you lived in Southie?
A. I grew up on Long Island. I moved to Southie in 2019. My first run [on “Jeopardy!”], they introduced me as “originally from West Islip, New York.” I changed it to South Boston partially because, since I was first on, friends who grew up in Southie told me I should say Southie. Which I know could be controversial. It’s like in “Jaws.” “You’re not born here, you’re not an islander.”
I mean it as an homage. It feels like home, a neighborhood in the truest sense. After my first episodes, I’d go to L Street Tavern, or the supermarket, and someone would grab me: “This is the ‘Jeopardy!’ guy!” My web of Southie people exploded because I was “Jeopardy!” Guy.
It’s funny: My first time on the show, my anecdote was: I rode my bicycle from the Canadian border down to Manhattan. Ken Jennings goes: “Oh, you didn’t decide to head out to the end of Long Island?” I didn’t know what to say; I was nervous. The first thing that popped into my head was: “I’m not missing much.” Ken laughed, the audience laughed — and when the laughter trailed off, you heard a few people go “Oooooh.”
Q. I remember that.
A. I thought: That’s going to come back to bite me. Then I completely forgot about it. A Long Island-themed Instagram account posted a clip and the hate comments — hundreds of people saying the worst about me.
A tabloid printed: Ken Jennings Left Stunned! A Long Island newspaper had a story. I was waking up to Facebook messages from complete strangers: [in Long Island accent] “I thought what you said was hawrrible.” “I hope you lose!” Then a friend from Long Island texted me: The radio station is talking [expletive] about you on-air right now. So I called in.
I go, “This is Sean McShane, the ‘Jeopardy!’ guy that everyone hates.” They go: “We’re on with disgraced “Jeopardy!” champion Sean McShane! Sean, what do you have to say for yourself ?” So I had to dial-up my accent: “It was a joke. I love Long Island!” [It eventually died down] but my friends and siblings thought it was the funniest thing: The first time Sean goes on TV he has to issue a public apology.
Some people might interpret my change of hometown as a [knock] to Long Island. I choose to frame it as a thank you to South Boston.
Q. You’ve had a job change since your last episode. You’re now a tour guide. A. For the Freedom Trail Foundation. I’d always seen [costumed guides] around. I thought: Seems like fun. And it’s a lot of fun. You get people from all over the world. Once you can get over wearing breeches, a cravat, and a tricorn hat in public, you’re golden.
Q. Has it helped with history trivia?
A. Oh yeah. I was a history major, but I only knew the American Revolution from high school. I think anyone who’s good at “Jeopardy!” would probably be good at this. My knowledge of the American Revolution is much stronger.