The Relentless Optimist: Jason Gregor’s path to becoming one of radio’s greatest philanthropists

Published on June 12, 2023

Sports radio host and 2023 Honorary Bachelor of Technology recipient uses his platform to give back

In Killam, Alberta, staring up at a bathroom sink in a hotel room, Jason Gregor (Radio and Television – Radio ’01) decided it was time to make a change.

He just wanted to sleep. Gregor had an oilfield job leading drilling rig inspection teams. The money was good but the roommates could be challenging. That spring night in the late-1990s he was trying to escape a champion snorer.

“So finally, at four in the morning, I grab the duvet off the bed and go into the bathroom,” says Gregor. Lying there, a thought occurred to him: “There’s gotta be more than this.”

Truth is, Gregor had been thinking about a change anyway. One reason was his work ethic, developed in part from tending cattle while growing up on a small farm 50 kilometres southeast of Edmonton. Another was sports radio host John Short, whom he idolized as a youth.

Gregor came home with a vague plan to channel his energy into pursuing a career in broadcasting. “I didn’t even know where to go,” he says. “I asked my mom – she’s a super smart lady, and she knew. She said, ‘You have to go to NAIT.’”

That set off the chain of events leading to The Jason Gregor Show, a fixture for 20 years on TSN1260 (known as Team1260 when he started). It was unique in that Gregor, a 2023 NAIT honorary degree recipient, owned the airtime, hosted and sold the ads.

But during its run before the station shut down in mid June 2023, the show also stood out for having raised more than $3 million for a variety of charities. And that owes largely to another key influence – Gregor’s late father, whom he once watched give $20 to a stranger for a bus ticket at a time when the family had little to give.

“We still have more money than him,” Gregor’s father told his son. “If you’re in a position to help someone, you should help them.”

And so, by talking sports, he does.

A unique path to radio – and giving back

Gregor entered NAIT with “blinders on.” He didn’t care that he was a terrible campus radio music DJ, because he was once the kid who could memorize the newspaper’s NHL stats page.

“I knew I wanted to be in sports,” says Gregor. “And that helped me.”

By third semester, he’d landed a part-time job with Short, helping cover Oilers’ home games. When Short’s regular producer got sick, Gregor stepped in nightly, using the job to replace an upcoming practicum. Then things progressed quickly.

In February 2004, Gregor and Short jointly bought a four-hour block of airtime on 1260; Short took 9 to 11 p.m. and Gregor followed until 1 a.m. A year in, the young broadcaster decided to try going solo.

“I’m 32 now,” Gregor recalls thinking. “I gotta sink or swim.”

On March 1, 2005, he launched Just a Game Productions; he landed the afternoon slot in 2008.

Gregor would soon prove himself as more than an entrepreneur. (Incidentally, he would also buy into the Nation Network, home to, co-founded by Jay Downton, Finance ’02; it sold to Playmaker in 2021 for $15 million.) Thinking of his dad’s lesson, Gregor began to explore fundraising on air and off.

“I didn’t know how good it would go,” says Gregor, “but Edmontonians and the surrounding area are incredibly generous. Most people deep down want to help others. They don’t necessarily know how they can or what direction to go.”

He began pointing them toward charities he chose for their impact and low administrative costs. In 2011, Gregor formalized the process with his show’s annual Month of Giving, in December, auctioning donated items and dedicating the proceeds to various organizations.

All told, that initiative raised $1.4 million. Combined with other efforts – including those of the Gregor Community Foundation, started in 2014 – the total surpasses $3 million. Beneficiaries have included everything from MS Canada to Santa’s Anonymous to young men in need of a suit for high school graduation (aka Gregor’s Grads). And NAIT students.

Each year since 2018, a third-semester student is awarded the $1,000 Jason Gregor Radio and Television – Radio Bursary. In addition to proving the need, there’s just one catch: Gregor asks to meet the students his bursary helps.

The 2023 recipient was Presley Cuthbertson, who’d been working at balancing school with commitments as a student athlete in curling and living on her own before she filled a maternity leave on the morning show at CISN. The cash helped pay bills, but the connection made during their coffee meeting proved truly invaluable.

“We talked a lot about how he got into the industry and made a name for himself and how I could possibly do the same one day,” says Cuthbertson. “It was like sitting down with a mentor.

“He even said if I ever needed anything, reach out to him.”

They also touched upon the persisting challenge of being a woman seeking a career in sports broadcasting, as Cuthbertson hopes to do, and coming to the industry from similar small-town backgrounds.

And, Cuthbertson adds, “we talked a lot about curling.”

A glass ¾ full

Whatever Gregor does with his show or radio in the future, he won’t always talk about sports. It’s tied in a way to wanting to spend more time with his nine-year-old son and his wife. They motivate him to find the balance, to slow down and be better at being present, and maybe, also, to continue to grow in his profession.

“There are some other things I want to talk about and look at,” says Gregor. “I don’t know when that change is but I do think it’s inevitable for me. I have a real thirst for knowledge. There’s so much I don't know.”

What likely won’t change are his beliefs about his role in the community and the good he might do. Gregor is optimistic by default.

“I’m a ‘glass ¾ full’ kind of guy,” he says. “If there’s a ‘what if’ scenario, I'll always gravitate toward, What if it works? Not, What if it doesn’t?”

Which means that a lot of people – students, community members, family – will be able to continue to come to count on Gregor’s ability to find ways to make a difference, on the radio or elsewhere. He may be driven to learn more, but he’s already learned a life lesson from his parents, from the generosity of listeners, maybe even from a sleepless night in Killam.

“When you have a platform,” says Gregor, “there comes a responsibility with it.”

Shopping Cart Quick View
Open Shopping Cart