It’s January in Boston, which means wherever you are, you’ll pass somebody running on the side of the road or swerving on sidewalks as they train for the Boston Marathon. It also means if you happen to walk by a certain apartment window in Southie, you might see a young man standing in front of his TV, gripping a click pen in his hand as he watches yet another Jeopardy! episode. But don’t worry, that’s just 3-time Jeopardy! Winner Sean McShane training for his own marathon, the Jeopardy! Tournament of Champions.

Ever since finding out he was selected for the tournament during a live CBS Boston segment, it’s been Go Time. Or study time. But before we hit the books, let’s take a commercial break and learn how McShane got himself on the show in the first place…

Family Affairs for $100

Growing up, McShane had a curious mind and was a voracious reader. But, he accredits his “weird ability to retain information” to the McShane side of the family. In fact, one could say it quite literally runs in the family, seeing how his older cousin went on Jeopardy! as well and won multiple times.

During the application process, one of the questions was, Do you know anyone who was on Jeopardy! before? If yes, when was the last time you saw them? McShane’s answer:  Thanksgiving.

“My joke had been that I wanted to go on the show and win just one more dollar than my cousin did,” he said. “I wasn’t playing for glory. I was playing for bragging rights on Christmas!”

Applying to Jeopardy! For $200

McShane had initially applied for the show back in January 2020 but never heard back. Two years later, he and his friends were at their weekly get together at L Street Tavern to unwind and watch Jeopardy!. Throughout the show, McShane’s friends kept egging him on about applying again. So, naturally, after closing out his tab he went home and took the application test again – the beer helped take the edge off.

9 months, another test, one interview, a mock game later and a follow-up phone call later, his phone buzzed while at his friend’s apartment. After reading the text three times to make sure he wasn’t imagining it, it was official. McShane was asked to be on Jeopardy!.

He told his mom, his boss (that he needed a few days off), and a few friends. Just in case he didn’t do well on the show, he didn’t want the whole world (or all of Southie) knowing.

One of his friends who didn’t know called McShane while he was at the airport headed to California. His friend said, “Where are you? It sounds like you’re at an airport.” To which McShane had to casually explain he was on his way to tape Jeopardy! as one does.

Being on TV for $300

Once arriving in California, McShane was set to tape four episodes back to back. Doesn’t your brain hurt just thinking about that? After the nerves settled down, he was feeling great by the end of Episode 1. How could you not when you finally look at your score and realize that you won?

“If you don’t look at Ken Jennings or the audience, it feels similar to you just watching at home,” McShane said, which was something he did a lot of to prepare for being on the show.

After Episode 3 and a few quick outfit changes later, he finally had a bite to eat and the chance to let what just happened sink in. The adrenaline high was gone, and he realized just how tired he was. He lost the next episode and it was time to return to Boston. While he was disappointed with the loss, he respected it.

“You don’t get mad when you get a question wrong, and it’s Ken Jennings telling you it’s wrong,” McShane said.

When he got back, the few people he told asked him how he did on the show, but due to NDAs, he had to keep his lips sealed during the 6-week turnaround time. All he could say was, you’ll have to tune in to find out!

And tune in they did, where else but L Street Tavern. McShane fully planned on picking up everybody’s tab that night, thanks to his winnings. But, night after night, as each episode aired and his friends wanted to watch, he didn’t pay for a single drink. His friends insisted on treating the champion

Not only were his beers paid for, but he had since been discovered on the streets! He’s been stopped and asked for photos and even referred to as Jeopardy! Guy! by a random passerby on the sidewalk. To McShane, that part has been weirder than seeing himself on TV!

Studying for Jeopardy! for $400

So, how did he prepare for the show and how is he preparing for the upcoming tournament? “There is no wrong way to study, but there is also no right way to study,” McShane said. “You have no idea what is coming.”

He spent an entire day brushing up on the U.S. Presidents. While he didn’t have time to read through ALL of Shakespeare’s work, he read the Sparknotes of plays. He made sure he knew a list of Oscar-winning movies and random geographical facts like the highest mountain or the longest river. But the best way for him to study was just watching the show. And, not for nothing, he had to practice using the buzzer – which surprisingly is something that does not come easy to contestants.

Before taping, they are told by producers not to be “Lady Liberty” and stick their buzzer in the air. A tip from a former contestant helped McShane practice the timing of buzzing in by listening for the last syllable of the clue.

Now that he’s got the buzzer under control, this time around, his focus is on his weak spots – theater and sports. Although he is making sure he learns the basics (like the names of all the professional teams) around a week before the taping, he won’t worry too much about soaking up any new information.

“If I don’t know it now, I’m not going to know it,” McShane said. “I am going to end up pushing something else out of my head.”

As for how he feels now, just a few weeks out from the Tournament of Champions? “I’m feeling alright. But, this time around, I’m more nervous because everyone knows I am going back,” McShane said. “The pressure is on.”
It looks like that’s all we have for you tonight on this episode of Caught in Southie.  Jeopardy! Tournament of Champions with Sean will air on March 6th! Enjoy this fun fact that McShane will close the show with: Puritan settlers originally named what is now Boston “Tremontaine” after the three hills that stood in what’s now downtown. This is where Tremont Street gets its name!


  1. Barry Jennings January 12, 2024 at 8:21 pm - Reply

    Good luck Sean. Take the plunge

  2. Justyn Tyme January 18, 2024 at 6:15 pm - Reply

    What schools did Shane attend to prepare him for his big day????

  3. kathy O January 18, 2024 at 6:52 pm - Reply

    good luck Sean you can do it!!!!!

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