Caitlyn Callahan made Pirates history, turning a can't-miss opportunity into a coaching job

Caitlyn Callahan’s initial interview with the Pittsburgh Pirates felt more like a casual conversation, so she was in her comfort zone in what amounted to an open audition for a job.

A day after an hourlong talk with minor league technology and video coordinator Marc Roche about a minor league operations assistant opening, the 26-year-old Callahan was invited to the Pirates’ Get Better At Baseball camp in Bradenton, Fla.

At Pirate City, it clicked for Callahan that she wasn’t there for her expertise in video or running a Raposodo machine when she saw the Pirates had minor league operations assistants handling those roles, but rather it was a working interview. Callahan made a positive first impression by pitching batting practice at a hitting session on the main field, taking over a drill that was supposed to be run by Pirates third base coach Mike Rabelo.

“I knew that I had to show that I could contribute as a coach,” Callahan said Tuesday in a video conference call. “I went up to the mound and was like, ‘This is my time. I have to show that I can contribute, I can help.’ At the end of the day, that’s why I’m here: I want to help the team get better every single day, just like Rabs. It’s funny. A lot of people have brought up that story. I was like at that time, I’ve got to prove that I can hold my own. I didn’t even think twice about it.”

For Callahan, it was quite the can’t-miss moment. Pirates hitting prospects were wearing occlusion goggles, which blurred their vision of the ball.

So Callahan knew she had to be spot-on.

The Pirates, looking to add talent and diversity to their system, soon made Callahan their first female uniformed coach in club history by hiring her as a minor league development coach based in Bradenton.

“She just impressed everybody from Day 1,” Pirates general manager Ben Cherington said. “Now, you don’t hire someone just for their BP, but I think it was illustrative of her courage and conviction and her ability. Over the course of the camp, we got to see that play out in a lot of ways.

“At a core level, she has the characteristics that we’d be looking for in any coach – a real passionate curiousity for learning, 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. She quickly seemed like someone who would be a good teammate amongst our staff.”

‘I didn’t think it would be possible’

For Callahan, it was the opportunity of a lifetime, one she dreamed about while playing Little League baseball in middle school. It was then that she started thinking about plate approach. Her interest in the sport grew to where she followed MLB games and realized that being involved in baseball as a career was something she wanted to do.

“To be completely transparent with you,” Callahan said, “I didn’t think it would be possible for me to be a coach.”

That changed in college, when she was injured for the majority of her career while playing softball at Boston University and St. Mary’s. Instead of serving as the end of her involvement in sports, it proved to be a catalyst. During injury rehabilitation, she picked the brains of her strength and conditioning coach and physical therapist, looking for ways to recover. She also started doing advance scouting reports for opponents and giving positive self-talks with pitchers while warming them up before games as a bullpen catcher.

After earning a degree in kinesiology, Callahan spent two summers working as assistant general manager for the Brewster Whitecaps in the Cape Cod League. The major leagues still seemed like a far-fetched dream.

That changed in November 2019. Callahan was in awe when she learned the New York Yankees hired Rachel Balkovec as hitting coach for their rookie-level team, the first woman to hold such a position. (On Jan. 11, Balkovec made more history when she was named manager of the Low-A Tampa Tarpons, another first in baseball).

Callahan said she’s “still pinching myself on a daily basis” to be working for the Pirates and counted among the sport’s trailblazers.

“It honestly knocked my socks off,” Callahan said. “I was like, ‘Oh my gosh. This is possible.’ So to hopefully be that person, that strong female for girls and women in Pittsburgh, it’s an honor. 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.”

‘I want to win a World Series’

Callahan spent the past two seasons as a minor league video and baseball technology intern for the Cincinnati Reds, and she realized her future while working with a player returning from a back injury to help him regain confidence in his swing. As she used video to show before and after swings, Callahan realized how much she enjoyed it.

“Seeing that success, seeing him come back was huge for me,” Callahan said. “That’s what I’m about. I want to make sure players are optimizing success, playing at our utmost potential.”

With the Pirates, Callahan found she’s surrounded by like-minded people, coaches and staff with a passion for the game and a willingness to use new and imaginative ways to teach.

She was reading Rob Gray’s book, How We Learn to Move: A Revolution in the Way We Coach & Practice Sports Skills on the plane to Florida, wondering whether the techniques would work as well in practice as they did in theory.

“Literally, in my mind while I was reading the book on the flight I was like, ‘This is a great idea, but how is it going to be executed?’” Callahan said. “It was hard for me to wrap my head around, ‘How is this going to be executed?’”

Then Callahan was talking with Pirates director of methodology Bart Hanegraaf about the club’s individualized player approach while watching coaches instruct minor league players in the batting cage. Curt Wilson, a fellow Florida Complex League coach, had catcher Abrahan Gutierrez working on a drill and as Gutierrez got comfortable, Wilson would change the environment to create game-like conditions. Jim Horner was doing similar work with outfielder Sammy Siani.

“I’m excited to be a part of it because this is something I’ve never seen before and it’s being executed well by people who care,” Callahan said. “It’s really, really unique. It’s really special, and I’m excited just to be a part of that. I’m gonna take it day-by-day. I don’t know what type of impact I’m gonna make, but I know that it’s not just gonna be me. It’s gonna be this team, this support staff, the coaches, the players. Every single person, it’s special. And I’m excited to see how it plays out.”

Callahan said she feels empowered and honored to be viewed as “that strong female for girls and women in Pittsburgh” and excited to be around “some of the brightest minds in baseball.” Callahan knows that she has a lot to learn but isn’t shy about stating her career goals.

“I think ultimately my biggest goal, hands down, I want to win a World Series in the next five years,” Callahan said. “I don’t know how that’s going to happen right now, right? But I know I’m going to show up every single day just like all of the other coaches and the staff. … I want to be part of this organization for the long haul and I want to win a World Series.”