From dreams to dugouts: reflections on a night of trailblazing women in sports

Wednesday night, four of us women from the South Side Sox staff had the chance to step inside a different kind of ballpark experience. It was built not on box scores or bullpen decisions, but on stories, representation, and the women helping push the sports world forward. The Chicago White Sox hosted the latest installment of their ninth-season event series, Game Changers, an initiative dedicated to celebrating underrepresented communities through powerful and diverse voices.

(Listen to our podcast about the event, or watch the podcast if you prefer.)

This year’s programming featured a special live recording of the award-winning podcast Sidelined with Brooke Fletcher and Dani Klupenger, held at Rate Field as part of the Game Changers Summit. Fletcher, well-known to White Sox fans as our beloved sideline reporter and a familiar presence on the Big Ten Network, brings a sharp, athlete-first approach to her storytelling. Klupenger, whose career spans the NFL and college football, college basketball and professional tennis, is a men’s college basketball analyst for Stadium Network (primarily covering the WCC and Mountain West) and a studio host for the Tennis Channel. Together, their show is known for candid, unfiltered conversations with women across sports and media.

That spirit was on full display as they welcomed special guest Kylen Mills, an award-winning sports broadcaster, former college athlete, and one of the most dynamic voices in modern sports coverage. Mills has soared as a play-by-play broadcaster and analyst for the PAC-12 Network, covered San Jose State football and basketball for NBC Sports Bay Area and contributed to MLS coverage on Apple TV. Previously, she spent three seasons covering the Golden State Warriors for KRON 4 News, including traveling to Boston for the team’s 2022 NBA Finals run. A Chicago-area native raised in a Bulls household, Mills recently experienced a full-circle moment when, on October 12, she did the play-by-play for a Bulls game. She brought both her professional insight and homegrown passion to the evening’s discussion.

Thanks to an incredibly generous invitation from Sheena Quinn, VP of public relations for the White Sox, we were able to be in the room for this thoughtful, lively conversation. Each of us left with our own takeaways and favorite moments — and in the spirit of Game Changers, we’re sharing them here together.

Kristina AirdoSports have always been a passion of mine and a huge part of my life, but when I was a young girl, I never really considered that working in the sports industry would be attainable. Fast forward 15-20 years later, and while not my “big girl job,” I now also get the opportunity to write about my favorite sport and cover my favorite team here at South Side Sox, alongside several other intelligent and driven women — including the other three writers of this story! And as we will all likely agree, it was an incredible experience to be able to attend the Game Changers event in the White Sox clubhouse, and to see the beautiful 2005 World Series trophy in the flesh — truly a marvelous piece of metal.

I have been obsessed with baseball since I was a little kid. I knew all the players, their positions, uniform numbers, and where they hit in the batting order. As you’d expect from listening to Hawk Harrelson shout through hundreds of games, I thought it would be fun to be a baseball broadcaster, but due to a lack of women in the space I don’t think that ever really clicked as an option for me. Hearing successful and knowledgeable women like Brooke, Dani and Kylen share their stories of how they got started in sports broadcasting is inspiring, especially for a woman who has just barely dipped her toe in the water into sports journalism. The irony of my story is that I went to arguably the best journalism school in the country (MIZ!), but did NOT major in it. That might be special in itself, because here I am anyway thanks to our editor, Brett Ballantini, taking a chance on me.

It’s essential to continue elevating women in sports and empowering women in general. I am lucky to have connected and engaged with these three ladies, and I look forward to continuing to learn from them. Special thank you again to Sheena Quinn and the White Sox for continuing to find meaningful ways to engage fans in the White Sox community, as well as providing opportunities to uplift women’s voices.

Hannah FilippoSitting in the Sox clubhouse surrounded by successful and inspiring women fulfilled two childhood dreams. Growing up loving sports, and especially baseball and the White Sox, I didn’t have any women with whom I could discuss sports beyond a surface level. I craved a community of women who shared my passion for sports and wanted to talk about the nitty-gritty of it all. It wasn’t until I sat in the Sox clubhouse, a place I only thought I’d be in my wildest dreams, that I realized I finally found that community.

Fletcher, Klupenger, Mills, and Quinn reminded me of why I write for South Side Sox: Women’s voices need to be heard in sports. These motivating and incredible women gave me an additional boost to keep putting my name out in the baseball community. As an aspiring baseball operations executive, I’m eager to meet other women in the industry who want to leave their mark and prove that women belong in sports.

Melissa Sage-BollenbachThis special evening struck a deeply personal chord for me. As someone in my mid-50s, being surrounded by so many women who are breaking barriers in the sports world left me both inspired and profoundly proud. When I was 11 or 12 and just starting to imagine what I might do in my life, my first dream wasn’t to be a ballerina or a teacher — the kinds of roles girls in the 1970s and ’80s were often nudged toward. But really, I wanted to be a major league umpire. I hadn’t played softball, but I loved baseball, I loved my White Sox, and I thought being on the field every day sounded like the most incredible job in the world. Even then, though, I understood that the dream wasn’t very realistic.

For a brief moment, I thought about broadcasting, but there just weren’t many women in sports media at all. And as the first person in my family to even consider going to college, I really didn’t see such a path forward. Life, as it does, led me in other directions, and I was fortunate to build a meaningful career in higher education, earning both my bachelor’s and master’s degrees and spending 15 years helping students find their own paths.

Then, three years ago, Brett sent me a message after seeing me talk about the Sox on Twitter. I couldn’t believe anyone would be interested in what I had to say about baseball. I’m still grateful that he was and that he valued my voice enough to invite me onto this staff. Opportunities like last night remind me just how remarkable that leap was.

If you had told 11-year-old Melissa that one day she’d be standing in the White Sox clubhouse at an event filled with women who had called games, reported from the sidelines, analyzed matchups and shaped conversations through entirely new mediums, she wouldn’t have believed you. Not because she doubted her love for baseball, but because she simply didn’t see women doing those things — not on her TV, not in the press box, not anywhere. The idea that she could someday be part of that world would have felt impossible. And yet somehow, life brought me here into a very sacred and special space where women aren’t just present, but are leading, innovating and making room for others. Being able to witness that firsthand, experience it with my colleagues, and contribute even a small voice to it is something I’ll never take for granted.

Allie WeselAs someone who has struggled over the last couple of White Sox seasons to stay engaged with the team and covering it for the site, this event was a true reminder of why I began writing for South Side Sox in the first place. You cannot deny that women have made huge strides in many industries, but too often I hear sentiments about why we are still making a big deal about it. Why is an all-female broadcast team a huge thing? Why do we have to celebrate every time a woman accomplishes something new? This space was a reminder of why.

Women deserve to be in these spaces; they deserve to feel supported and have their opinions valued. The event touched on the progress we’ve made, but it also highlighted how far we still have to go and the stigmas we must continue to fight. No one journey of a woman in sports is the same, but they all have the common thread of wanting their voices heard and respected in the sports space. From soccer to tennis to baseball to college football, these women discussed their journeys to where they are and the goals they still hope to achieve. It was a wonderful reminder of the importance of having women on this site and of the unique perspectives we bring to this industry as a whole.