Toni Callahan has grown accustomed to watching her daughter defy expectations.
Born into a baseball-loving family, Caitlyn Callahan was 11 months old when she attended her first MLB game. Her first part-time job was keeping score for Little League games, and she began playing travel softball late because she was having too much fun competing against boys in baseball.
Yet most telling of Callahan’s understated-yet-unrelenting drive might have been this: Toni and her husband, Paul, learned Caitlyn would spend the 2017 summer working for the Brewster Whitecaps of the Cape Cod Baseball League the day she was hired; knowing she needed an internship and wanting it to involve baseball, Caitlyn without any fuss or fanfare applied and made it happen, like she was picking up a job at Dairy Queen.
“She loves the sport more than anything,” Toni said. “It’s always been what she’s wanted to do.”
The Pirates’ December hiring of Callahan as a development coach was nothing short of groundbreaking, with the San Marino, Calif., native becoming the first uniformed female coach in franchise history, but there’s also a matter-of-factness at play here, too.
Callahan got the job because she’s qualified, a testament to her college softball experience (she played at Saint Mary’s College of California and Boston University), insatiable appetite for learning and desire/ability to help others improve. It’s a hiring process for which every organization should strive, to bring in the best and brightest, sex or skin color be damned.
“They’re looking for the best candidates,” Callahan said of the Pirates. “It has opened doors for women who work hard, and I’m excited to be part of such a strong culture as far as people who want to work hard and get better every single day.”
But as simple as Callahan’s hire might seem to some, it’s bigger than entrusting coaching jobs to the right people, even if one happens to be a woman. Five years ago, Callahan getting this job might’ve been iffy at best. Ten years ago, forget about it.
Thankfully, recent MLB-wide hires such Sewickley native Bianca Smith (Red Sox minor league coach), Alyssa Nakken (Giants major league assistant) and Low-A Tampa Tarpons (Yankees) manager Rachel Balkovec have broken barriers and disrupted the old way of doing things, paving the way for people like Callahan and others.
“Part of the reason I have this opportunity is because of what these very strong, prominent female coaches have done,” Callahan said.
Now, she has the opportunity to play the same sort of role for young girls in Pittsburgh and around the country.
“It’s an honor,” Callahan said. “I don’t take it lightly by any means.”
Early seeds
The idea of a career coaching actually traces back to Callahan’s college softball days, when she said she was hurt for much of her career. Unable to play, that became the “catalyst” for improvement, whether in the weight room, training room or otherwise trying to get back on the field.
A catcher by trade, Callahan would chat with pitchers to try and get inside their heads, using her knowledge and experience to help them improve, the same thing she caught herself doing while watching video with a player rehabbing a back injury with Class AA Chattanooga.
“We’re putting video up next to each other, and it was like, ‘Hold up. This is something that I can see myself really enjoying.’ 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.”
Although Callahan knew from an early age what she wanted to do, she didn’t know if it would be possible, unfortunately a common theme for women trying to make it in baseball. Some recent moves around the game, however, have changed those opportunities.
“When I heard about Rachel Balkovec [the first female manager in the history of affiliated baseball], it honestly knocked my socks off,” Callahan said. “I was like, ‘Oh my gosh. This is possible.’ ”
Despite her time spent in the Cape (rising from MLB scout liaison to assistant general manager the next summer), a stint as a baseball operations assistant with the Staten Island Yankees and her most recent gig as a video and technology intern with the Reds, one of the jobs that has resonated most with Callahan was when she worked as a server.
She waited tables to make ends meet when the Reds laid her off for 10 months in April 2020. She did it again this past offseason while awaiting her next opportunity in baseball.
“I’ve been a lifeguard. I was a rock-climbing instructor at one point,” Callahan said. “You do whatever you have to do to make it.”
’Crush this role’
Ironically, waiting tables had an indirect influence on how she wound up with the Pirates, too.
It was between shifts at a place called Buck & Rider in Phoenix that Callahan heard from Katie Krall, a former baseball operations assistant with the Reds who in January was hired as a development coach with the Red Sox. Krall saw the Pirates had an opening and encouraged Callahan to apply. Initially, Callahan demurred.
“She sent me the application and was like, ‘You need to apply,’ “ Callahan explained. “I said, ‘Yeah, maybe, I don’t know.’ And she was like, ‘Own that. You would crush this role.’”
Krall got to know Callahan through a pair of mutual friends: Amanda Brady, an advance scouting analyst for the Yankees, and Sam Schultz, who’s a pitching development analyst for the Athletics. The first time they met, they talked for two hours over dinner at a Panera Bread-style spot in Arizona.
The biggest thing about Callahan that resonated with Krall was her ability to take what she learned and apply it to specific processes, which was put on display this past season when Callahan pushed Krall to expand some of her video work into the analytics realm.
“She’s super passionate about baseball, but she also has a great feel for knowing where to add her input and where her career can lead,” Krall said. “You know how people like to say that [former Giants catcher] Buster Posey was always three pitches ahead? I feel the same way about Caitlyn.”
Never one to be unprepared, Callahan tapped into another resource after deciding to apply for the gig. During her time with the Reds, Cincinnati’s former minor league director of pitching initiatives/pitching coordinator Kyle Boddy (who’s better known for founding Driveline) introduced Callahan to Balkovec, and the two struck up a friendship.
They actually bonded over the hiring and training process of the restaurant group (Hillstone) where Callahan used to work, because Balkovec once held a job there during her own waitressing career.
“It was very much one of those things where it was like, ‘OK, that’s all I need to know,’” Callahan said. “Rachel was very insightful, very knowledgeable and super supportive.”
‘I’m bought in’
Callahan interviewed with Pirates minor league technology/video coordinator Marc Roche, although she insisted it felt nothing like an actual interview. It quickly went from formal to an open discussion about players and various ways to help them improve. Callahan described it more as a conversation.
The next day, Roche invited Callahan to attend the Pirates’ “Get Better at Baseball Camp” in November, where she’d help players during what was effectively a working interview, one that would further cement Callahan’s belief that she was traveling down the proper path.
An avid reader and podcast listener, especially when it comes to anything about coaching or how to lead a group, Callahan happened to be reading a book by Rob Gray called “How We Learn to Move: A Revolution in the Way We Coach & Practice Sports Skills” when she reported to LECOM Park.
Callahan was absolutely floored when she joined up with Florida Complex League hitting coach Curt Wilson, who was putting into practice with Low-A catcher Abrahan Gutierrez much of what she was reading about in the book.
As soon as Gutierrez got comfortable with a drill, Wilson changed it in some way, always keeping it as game-like as possible. Crazier still, the book was actually something head of methodology Bart Hanegraaff had purchased for the entire staff.
“Curt was leading a horse to water, and Abrahan was drinking,” Callahan said. “He was verbalizing what he was feeling, what he was doing. It was so incredible to see because I really feel that’s the way coaching is trending.
“I can’t tell you how many of those moments I had in that five-day span.”
It’s impossible to tell how many moments like that Callahan will have in the future, although now that she’s playing an important role for the Pirates, it’s something that — like many things — she’s interested in learning more about, the same as her predecessors pushing every boundary possible.
“The Pirates are doing a lot of really cool, new things, and I’m excited to be on the ground floor and witnessing it every single day,” Callahan said. “I’m bought in, and I want to make a difference. I’m excited to be a part of such a strong culture as far as people who want to work hard and get better every single day.”
Callahan said her goal is to win a World Series within the next five years. It’s a tall task, for sure, but one she seems to think is possible in Pittsburgh.
“I’m excited to be a part of it because this is something I’ve never seen before,” she said. “And it’s being executed well by people who care.
“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.”
‘You’re not alone’
While Callahan has enjoyed the Pirates’ new way of coaching, she has been equally as excited by the fact that she has company. A lot of it, actually.
A few days after she was hired, Callahan was added to a text thread involving all of the women working in baseball operations, an ongoing conversation Callahan described as “strong females empowering each other.”
One of the women already in the group is business manager Sarah Steinberg, who works as a liaison between the baseball and business sides, alternately consulting with finance over the baseball budget and human resources for culture-based initiatives.
Steinberg has a similar story, too. She attended every University of New Mexico baseball game growing up (her older brother Nate was the bat boy) and fell in love with keeping score. Although she was a competitive dancer, Steinberg was also a manager for the football and baseball teams.
Steinberg went to UMass-Amherst, interned on the Cape and cut her teeth as a strategy and development intern with the Rays, later folding that into a stint with the Mets as a player development/video intern and 21 months with the Astros as a minor league operations assistant, where she’d work directly with Balkovec.
After a year spent out of baseball, Steinberg jumped at the chance to take on what is essentially a dual role with the Pirates.
“Women are getting more diverse opportunities and not just on the business side,” Steinberg said. “They’re on the baseball side in different capacities. I think it’s amazing and, yeah, about time.”
Steinberg and MLB scout Kinza Baad, who has been with the Pirates since May 2017, both serve on the Alliance for Gender Equity in Baseball, a board on which Balkovec serves, as well.
In addition to the Pirates’ team text thread, there’s another one that exists around the league to serve a similar purpose: to help women in baseball pull together and root for one another.
“It’s good to know you’re not alone, and you can celebrate together, as well,” Steinberg said.
The way Baad sees it, having more women in baseball is twofold. On one hand, she said there’s an inherent fear that people like her, Steinberg, Callahan or others might pour everything they have into this, then not get a legitimate opportunity because of their gender.
The second one is a little more stripped down and simple, the same reason the Pirates hired the highly regarded Callahan to improve their video processes and how they work with young players.
“I’m just happy we’re hiring the best people,” Baad said. “We’re willing to open up who we look at to the entire population, and that’s how you win a championship — by getting the best people.”
The full list
In case you’re curious, here’s a full list of women working in the Pirates’ baseball operations department:
• Sarah Steinberg – Baseball Operations
• Christine Harris – Research and Development
• Hilary Ake – Sports Nutrition
• Rachel Sharley – Sports Nutrition
• Katie Killian – Physical Therapist
• Alexa DeHaeseleer – Athletic Trainer
• Mayu Fielding – Coach and Player Development, Education
• Paige Moshier – Coaching and Player Development
• Caitlyn Callahan – Coaching and Player Development
• Stephanie Lombardo – Coaching and Player Development
• Kinza Baad – Scouting
Jason Mackey: jmackey@post-gazette.com and Twitter @JMackeyPG.
First Published: February 1, 2022, 7:30 p.m.
