From public school teacher to professional baseball coach.

It’s not a jump that many educators get to make.

Of course, there aren’t many high school teachers with the sort of baseball resume that Mississauga native Ashley Stephenson has put together. 

Stephenson, one of the most decorated players in the history of Canadian baseball, will join the coaching staff of the Toronto Blue Jays’ High-A affiliate Vancouver Canadians this season, becoming the second female coach in the history of the franchise.

But in doing so she’ll have to put her nearly 20-year teaching career on hold and leave her job as a physical education teacher at Dr. Frank J. Hayden Secondary School in Burlington.

Stephenson says she’ll miss teaching, but coaching for the Jays is nothing short of a dream come true.

“When I was a kid, I went to a World Series game [in Toronto], my mom and I drove around Toronto and Mississauga honking the horn. I would have been delighted to have an opportunity with any ball club, but the fact that it's the Blue Jays, it's like your team, right,” Stephenson said of the opportunity during an interview with CP24 this week.

“I rooted for them my whole life and to now be able to throw on the Jersey at some point, it's just borderline unfathomable, but simply a dream come true.”

Stephenson retired as a player in 2019 after a 15-year career with team Canada, during which time she won two silver and four bronze Women’s Baseball World Cup medals, along with a silver medal from the 2015 Pan Am Games.

She then quickly jumped into a role on the team’s coaching staff, helping lead team Canada to a bronze medal at the COPABE Women's Pan-American Championships in 2019 and becoming the first woman to manage the women’s national team when Canada played a five-game series against the U.S. in Thunder Bay last year.

She told CP24 that she knew early on during her playing career that she’d one day pursue coaching, and that her many years as a teacher and coach have prepared her for the job.

“I think one of the big things is just being able to communicate with players. Getting to know them, and getting to know what makes them tick. It's like your students, right, every student’s different,” she said.

“Everybody has their own set of circumstances and their own things that kind of get them going, whether it's a pat on the back or a little bit of motivation or something like that. So having experience with a lot of different kids and young adults I think will really serve me well.”

Last season, the average age of a High-A player was 22 to 23 depending on their position, according to Baseball America.

Stephenson says being a former player will also help her connect with the young pros she’ll be working with.

“I think as a player, you learn how hard the sport is, right. As a coach, sometimes you just forget,” Stephenson said.

“If you hit .300, you are a Hall of Famer. That's crazy - in no other sport do you just fail so often, and so I think as a player and having a lengthy career, you understand the highs and lows of the sport and you understand how hard it is. So I think that's really going to help me relate to players and just understand the psyche of it all.”

Inspiring the next generation of female baseball players

Last season, the Blue Jays hired their first-ever female coach, Jaime Lever, of Georgetown, as a hitting coach for the team’s affiliate in the Florida complex league, a position she will retain this season.

Stephenson says she hopes that she and her female counterparts in the professional baseball coaching ranks can help inspire the next generation of girls with dreams of going pro.

“There wasn't a lot of [female coaches] when I was growing up, honestly, probably not even until like, five, six years ago, really. And if there was, there was one or two and when there's only one or two, you never assume that it could be you,” Stephenson said.

“Before, there was a lot of really smart women involved in baseball, doing some things behind the scenes like biomechanics and analytics, and although their job is amazing, if you don't know that they're doing that, you wouldn't see them and you wouldn't know.”

Stephenson says that it’s important to continue making female coaches more visible to fans.

“Now if you take your little girl to the ballpark, you can see someone standing at first base or in the dugout who looks like you. So automatically, whether they know it or not, at least it's in their brain that, ‘oh, I can do that because I see somebody who looks like me,’ and I think that's really important.”

Stephenson’s baseball journey

Stephenson’s love for baseball began like many others’: at a young age, playing t-ball with her dad.

“I started playing t-ball when I was only four or five years old. My dad introduced me to it,” she said.

She says she took to the sport right away, eventually transitioning to softball.

“I played [softball] for a couple of years and then in my area, in the GTA, an all-girls baseball league started up and that intrigued me more than playing softball because I used to watch the Blue Jays and kind of dream about being a professional just like everybody else does.”

Stephenson’s legendary playing career with Team Canada took her all over the world, but she says one of her most memorable achievements was her team’s second-place finish at the 2015 Pan Am games which were held in the GTA.

Canada's Ashley Stephenson

“The Pan Am games was really special because it was a multi-sport games. In my 15 year career, it was the only time I got to participate in a multi-sport games and it's just a totally different beast,” she said.

“The Canadian Olympic Committee, after hosting the 2010 Olympics, the same group basically hosted the 2015 Pan Am Games so I have friends who had been part of the Olympic games before and they said it was as close to an Olympic Games as any [Pan Am Games] has ever been, so that was kind of the pinnacle of our career.”

Stephenson also played hockey growing up, and became a star at Wilfred Laurier University, winning four conference titles and a CIS National Championship.

She went on to play professionally in the National Women’s Hockey League and the Canadian Women’s Hockey League.

‘We’re here to stay’

Stephenson says despite the success she enjoyed throughout her long career, she’s also experienced her fair share of adversity.

“The fact that I'm female and in a predominantly male dominated sport, you know, I'd be lying if I said I didn't experience sexism or anything like that, but I try to surround myself with really positive people who want to help me get better,” she said.

“[But] I played on all-girls teams and we played against boys during the season in order to help us hone our skills and we heard things all the time. I used to get much more irritated when I was younger, not really understanding what the big deal was, but now I look at it always from the perspective of education, and maybe that's the teacher in me, but I truly believe if people who know better, they'll do better.”

Stephenson says that as more women are given a chance to prove themselves in professional coaching, they’ll continue to show that they’re just as capable as their male colleagues.

“I fully expect to have to prove myself, but I just want to be given the same opportunities that any of my male counterparts are given; no more, no less,” she said.

“And so now when people ask or they say things, I just [say], ‘this is my background, this is how many years I've been in baseball,’ and if they still disagree with me, that's fine. I don't have to change everybody's mind, but I will just politely agree to disagree that we deserve to be here and we're here to stay.”