Growing up, Caitlyn Callahan did not live in a neighborhood where girls played much softball. She said Little League Baseball was the name of the game, and she nearly quit playing ball at a young age.

“I was going to stop playing [softball] until my little brother's Little League coach was like, 'Why doesn't she try out for the Little League Baseball team?'” she recalled. “So I actually stopped playing softball right around middle school and started playing baseball.”

Callahan took that road into baseball at an early age, became passionate about the game and that love never stopped. After playing college softball at Boston University and St. Mary’s College of California, she followed her dream by working in baseball’s amateur and pro leagues.

Now, Callahan joins a wave of women making their name on the field for MLB clubs. In December, the Pirates hired her to be a development coach, making the 26-year-old Callahan the first woman to be a uniformed coach in the organization’s 135-year history.

“To hopefully be that person, that strong female for girls and women in Pittsburgh, it’s an honor,” she said on Tuesday, ahead of National Girls and Women in Sports Day on Wednesday. “I’m really excited to be around some bright minds in the baseball world. I still have a lot to learn, but I’m excited to learn every single day.”

In just a few years since graduating college, Callahan has grinded through many different positions in baseball: An MLB scout liaison and assistant GM with the Cape Cod League’s Brewster Whitecaps, a baseball operations assistant with the Staten Island Yankees and, most recently, a Minor League video and technology intern for the Reds from 2020-21.

Yet like many other people working their way up the baseball ranks, she found herself doing temporary offseason work this winter as a server in Arizona. That’s when she got a call from Marc Roche, the Pirates’ Minor League video and technology coordinator, whom Callahan had interviewed with previously for a job similar to her role with the Reds.

“Initially, I thought that when Marc called me, that it was they needed someone to run a Rapsodo or they needed someone to help with video [at a camp], and I was more than willing to help in that department,” Callahan said. “... Upon arrival, they have Minor League ops assistants there doing that. It kind of clicked to me, ‘Oh wait, this is a working interview.’ I knew that I had to show that I could contribute as a coach.”

So Callahan demonstrated the confidence she’s had in herself for years. Pirates GM Ben Cherington recalled stories of her effectively kicking third-base coach Mike Rabelo out from throwing batting practice and doing it herself, a decision she said she didn’t think twice about. But it was much more than her confidence that showed through to the Bucs.

“At a core level, she has the characteristics that we’d be looking for in any coach,” Cherington said. “A real passionate curiosity for learning about the best and most modern coaching practices. She’s certainly literate in all of the forms of technology we would use in player development. Most of all, she wants to help players get better and is passionate about putting the player first and doing whatever she can to help the player get better.”

Callahan admits there were times she didn’t know if she could be a coach – not because of any doubts of her capabilities, but because she had seen few women approach that level in pro baseball. When Rachel Balkovec was hired in 2019 by the Yankees as a Minor League hitting coach, everything changed.

“I remember where I was when I first saw she had been hired as a coach," she said. "I remember pulling it up on my phone and reading it and just being in awe. Like, ‘Oh my gosh, this is real.' People like her and [Red Sox Minor League coach] Bianca Smith paving the way, it's empowering and it's really cool to be a part of that."

A few years later, it’s become real for Callahan. Speaking with Pittsburgh media on Tuesday, she not only thanked those women who coached before her, but gave shoutouts to women in the Pirates' on-field operations, including pro scout Kinza Baad and Minor League operations assistant Paige Moshier.

Being a part of that group still hasn’t quite set in for Callahan yet: “I’m still pinching myself on a daily basis,” she said. But her resilience in the face of rejections for coaching positions and doubts about her future propelled her to make history with the Pirates, and she hopes it sets an example for other girls and women who have a passion for baseball.

“I may not have gotten that coaching position last year, but I went back with the Reds and I did that job to the best of my abilities,” Callahan said. “I showed up every day and tried my best, and it set me up to be in the position I'm at this year.

“Things happen for a reason. Stay persistent.”