“If I Don’t Do This, I’ll Go Crazy”: Keegan Matheson’s Journey to The Show

The fluorescent lights of a Halifax Scotiabank branch were never meant to be the backdrop of Keegan Matheson’s life. He remembers sitting at his desk, the glow of a computer monitor reflecting off his face. “I was good at the job,” he said, “but I hated it. I just plain hated it.”

That quiet dread became a turning point. One afternoon, Matheson realized he could not keep doing it. He left his desk, walked away from the security of a steady career, and started chasing something that had long felt out of reach: a life in sports journalism.

Today, Matheson is the Toronto Blue Jays beat reporter for MLB.com, one of the most recognizable voices in Canadian baseball. His journey from rural Nova Scotia to Toronto’s media spotlight is built on self-belief in an industry that often feels inaccessible to outsiders. 

Matheson’s story reflects the reality of trying to break into sports journalism as someone looking in from the outside. His rise was not built on luck or connections but on persistence and a willingness to do whatever it takes. Matheson’s story stands as proof that you can still break through with just your own sheer will. 

Being an Outsider 

Matheson grew up in New Glasgow, N.S., a town of just over 9,000. The world outside felt distant. “You know what a teacher is or a doctor is … but I didn’t know what a sportswriter was,” he admitted. Growing up as a fan from afar, the idea of covering the Blue Jays was alienating. 

After graduating from high school, Keegan sought to begin his career as a writer. He was headed to Dalhousie University for English and Creative Writing, where he would also work as a lobster fisherman on the side to afford his way through school. After Keegan earned that degree four short years later, he followed what seemed like a safe path: a desk job at Scotiabank in Halifax.

The office routine, however, left him uninspired. “That taught me that I needed to do something that I was actually passionate about and really enjoyed. In the sense of, if I don’t do this, I’ll go crazy,” he reflected.

Matheson quickly then decided to leave the Maritimes and his job at Scotiabank, a decision that was neither calculated nor cautious. He credits “young stupidity” for his breakthrough. “I was young and I was broke,” he said with a laugh. The move to Toronto in September 2015, approximately 2,000 kilometres from home, was daunting, and fitting in proved to be a challenge. “I hated Toronto. I absolutely hated it.” Keegan said.  

In hindsight, Matheson recognizes it was more about himself than the city. “I realized that I was just unhappy, so I took it out on Toronto. I had a bubble and I didn’t really let myself explore,” he said.

Once Matheson was able to look beyond his East York apartment into the city, he realized his dream, everything he’d been working towards, was sitting right in front of him.

Back to School

In 2016, Matheson jump-started his career by enrolling in the Sports Journalism program at Centennial College. The program became “a sandbox for me to experiment in,” he said. It was also where he began forming local connections, including one with Braydon Holmyard, now a sports assignment editor at the Toronto Star.

Holmyard remembers him vividly: “He was all business when it came to school. He was ahead of the curve in the class. He had already been running a Jays blog and doing Jays radio hits.”

Malcom Kelly, founder of Centennial’s sports journalism program, said Matheson’s small-town work ethic stood out. “He had to work his way through Dalhousie working as a lobster fisherman,” Kelly said. “That tells you what an incredibly hard worker Keegan is.” Kelly calls him “my favourite grad ever,” adding that Matheson didn’t wait for opportunities, but he inserted himself into the industry.

Holmyard added, “Once he figured out what he wanted in 2015, and then went to school in 2016, he’s just been motivated to reach where he is today. He’s always been extremely driven.”

Beyond the ability for the year-long sports journalism program to build the foundation for Matheson’s career, it also came with its learning curves. 

In 2016, Matheson and the sports journalism program had the opportunity to cover the Paralympics in Rio De Janeiro, Brazil. Keegan recalled, “It was an immense opportunity.” However, transitioning from the Maritimes to the Olympics in a few short years was not easy; it never would have been easy. However, it gave Matheson a head start on what was to come. 

Building Something From Nothing

After graduating from Centennial, Matheson completed a 10-month internship with MLB.com as an associate reporter, a significant step up, but still short of a full-time job. “After that season, I had to decide what to do … there were no jobs on the Blue Jays beat,” he said.

Rather than wait, he took matters into his own hands, launching a subscription-based website titled Baseball Toronto on February 2, 2018. “It was really fun. It was also overwhelming and nearly killed me and nearly bankrupted me. But it kept me afloat long enough for my current job to open up, he recalled, eight years later.

Holmyard remembered the moment vividly. “I remember seeing him lying on the floor of his apartment when the website went live. He was working around the clock to get it up and running.”

Matheson laughs about it now, but the struggle was real. “I was probably a month or two from being completely out of money.”

What began as a desperate move soon became his defining moment. Matheson’s pure ambition to create the independent website, along with its professional polish, caught the attention of the industry. Within months, the baseball world took notice.

By mid-2019, MLB.com came calling for Matheson’s services again. This time, the offer was for a full-time position. His gamble had paid off; Matheson had caught the dream.

Battle with Burnout

The grind did not stop once he earned the Blue Jays’ beat in 2019. All of his obligations caught up with him, and it took a toll on Matheson’s well-being. “I would cover a game, I’d be doing radio hits just after midnight outside the bus station, and I’d wake up at 6 a.m. to start doing radio the next day,” he said. 

That relentless drive accelerated his success, but it came at a cost. “I’ve struggled with that relationship because part of that is why I’ve made it a little further in my career, but it also drove me crazy when I did it,” he admitted.

Now, Matheson has learned to reclaim his time. “At this point in my career, I’ve stopped saying yes to a lot. I’ve allowed myself to start saying no. I’m constantly serving other people and entities, and their interests. So I need to block off parts of my day that are just for me,” he said. Holmyard had seen the change: “Now he’s at a more steady place in his career, and I think he’s found a good balance.”

That approach is reflected not only in his coverage but also in his book, The Franchise, released in June 2025. “A book felt like an opportunity to really branch out,” he said. “It felt like such a different style of writing in a very exciting way for me. I enjoyed it, and it was way more fulfilling than 100 MLB.com stories could ever be.”

Closure

Matheson’s story represents something bigger than baseball. Kelly said, “If you have talent, if you work hard, they will find you.”

Holmyard echoed that sentiment. “There’s only one MLB.com Blue Jays reporter. Thousands of people covet that job.” He said Matheson’s “small-town work-hard mentality” has played a key role in his success; it is his dedication, starting from nothing, that has gotten him where he is.

Even after years in the industry, Matheson continues to push himself. “I always need something I’m chasing,” he said. “I see many examples around me of people who have parked the bus … I would lose my mind.” Now, Matheson has expanded beyond journalism to appear as an analyst on TSN’s OverDrive, marking his next venture in an already impressive career.

Finally, as another night winds down at the Rogers Centre, Matheson packs up his laptop in the press box, another story filed under the stadium lights. “I love where I’m at,” he said.

From the hum of a Halifax Scotiabank branch to the roar of 50,000 fans at Rogers Centre, Matheson’s journey is one of dedication. He walked away from stability to follow a dream that few around him understood, and built a place for himself in an industry that was once alienating. For Matheson, that uncertainty has never been something he fears, but rather the fuel that drives everything he does.