Every Monday night, Jeff Sinclair descends from atop his Mountain of Trivia to test the knowledge of patrons of the Good Will Social Club.

While he hovers above the crowd, Sinclair takes a laid-back approach to hosting. Primarily, he wants the questions to be the thing that brings people back week after week.

“I just try to be myself. I don’t try to be anything bigger,” Sinclair says. “I’ve been to trivia nights where people wear the wacky hat or sparkly vest, and there’s nothing wrong with that, but that’s not me. I try to be the same person in the spotlight and out.”

Like many, Sinclair grew up watching game shows like Jeopardy! and Wheel of Fortune with his family. When he came of age, he began to go with groups of friends to trivia nights at bars around Winnipeg. He continued the tradition while living in Seoul, South Korea and working as an English teacher.

At the time, Sinclair was moonlighting as a standup comedian and improv performer. One evening, a bar manager asked Sinclair to host their trivia night after hearing he was a regular. Sinclair quickly took to the role.

“Trivia night is a great place to meet people,” he says. “Especially when you are abroad, you need a place to meet people and make new friends. It turns out trivia is a great venue for that.”

Sinclair has gained a passion for sharing interesting facts and tidbits with the growing community of people who regularly come to see him at the Good Will or one of his other three gigs around the city.

This connection with people is what draws Sinclair to the role. Since 2019, he’s hosted Mountain of Trivia events at the Good Will. Reflecting on highlights, Sinclair thinks back to seeing people’s reactions as they meet, talk, have fun and argue a little over a particularly tough question.

“After I have asked a question, I get to listen to everyone try and figure it out and discuss. You hear people say ‘no, no, you’re wrong’ or ‘no, absolutely, I know it.’ You hear these little things, and when you give the answer, you hear the reactions.”

Viewing his role as “a curator of trivia,” Sinclair strays from brain-busting questions, instead focusing on lumping bites of knowledge together in fascinating categories.

During the planning process, Sinclair likes moments where “you have given a lot of detail or cross-sections of a clue, and people have to figure it out.” A favorite example is: “What actor has been killed by an alien, predator and a terminator?” (Turn to page 6 for the answer.)

Sinclair still loves playing trivia and sometimes asks regulars to come up with their own trivia night so he can play. One of his frequenters, Sam Doucet, started hosting trivia at Shannon’s Irish Pub. Sinclair couldn’t be more excited.

“It’s the same thing with standup. You notice something, and other people notice it, too, and then when you say it and people stand up and go ‘yeah, I noticed that, too!’” he says. “It’s finding a connection with people.”

For Sinclair, hosting is all about experiencing and facilitating connection between people. It must be why people keep gathering at the foot of the Mountain of Trivia to hear him speak.

The next Mountain of Trivia is on Jan. 23 at the Good Will Social Club (625 Portage Ave.). Trivia starts at 7:30 p.m., but seating is limited, so get there early!

Published in Volume 77, Number 15 of The Uniter (January 19, 2023)