Jenny Brannan has called Winchester home for nearly her whole life. Growing up as Jenny Bishop, she spent countless hours at the Frederick County National Little League fields — a place where dusty cleats, sunburned afternoons, and lifelong friendships were stitched into every inning.

Jenny’s story is a familiar one for anyone who grew up around a ballpark. Her parents, Terry and Donna Bishop, were pillars of the league, volunteering countless hours in the concession stand and beyond. Their names are even etched on a plaque at the field — a quiet testament to their love for the game and the community.

Following in their footsteps, Jenny picked up a bat and a glove and never looked back. She played from the time she was nine until she aged out at eighteen, moving through the Minor League, Major League, and Big League divisions. Some of her fondest memories come from those years — not just the games won, but the lessons learned.

One moment, in particular, stands out. Jenny was twelve years old, playing in the district tournament. Her team was down five runs heading into the final inning — a nearly impossible mountain to climb. But then something magical happened. They rallied. Six runs in the sixth inning. A comeback for the ages. That victory sent them to the state tournament, and from that day on, "Six in the Sixth" became their battle cry — a reminder that no game was ever out of reach, no dream too big to chase.

Jenny and her teammates stayed together for years, winning another district title at seventeen and capturing a state championship in Luray. They even went on to play in the regionals, chasing a spot in the Softball World Series. Through it all, the friendships they built proved stronger than any scoreboard.

Today, Jenny Brannan stands on the other side of the fence. She now coaches her daughter’s Minor League softball team at Frederick County National. Though life has grown busier, the pull of the ballpark — the pull of community — never really left her. Coaching is her way of giving back, honoring the generations that came before and investing in those still to come.

Reflecting on her years in the league, Jenny sees more than wins and losses. She sees how softball shaped her work ethic, her resilience, and her sense of responsibility to her community. She learned early that success doesn’t come without sacrifice — that sometimes you give up summer camps and lazy days because your team, your goals, and your passion are worth it. She learned what it meant to lose gracefully, to win humbly, and to value every teammate like family.

Those lessons came largely thanks to volunteers like her dad, who coached her throughout her entire Little League career. He was tough, especially on her — not because he expected less, but because he believed in her potential. It was never about being the best on the field; it was about becoming the best version of yourself off it.

That’s why Jenny believes so deeply in the "Pitch In for the Future" Capital Campaign. Travel leagues are pulling young players away with promises of better facilities and bigger opportunities. But Jenny knows — not every family can afford those paths. Frederick County National must rise to meet this moment, providing local kids with the same quality facilities and chances to grow without leaving their community behind.

Back when Jenny played, there were no indoor batting cages, no year-round practice spaces. Today’s players deserve better. They deserve a place where a rainy day doesn’t cancel practice, where winter workouts build stronger athletes, and where every kid — no matter their background — feels like they belong.

Jenny’s hope is simple: that the next generation will experience the same magic she did. That they will make their own "six in the sixth" memories. That they, too, will learn that a ballfield is more than just grass and dirt — it's where life’s greatest lessons are taught.

Supporting "Pitch In for the Future" isn’t just about upgrading fields. It’s about investing in the next Jenny Bishop Brannan. It’s about building a community where every child, no matter how big their dreams, has a place to start swinging for the fences.

Learn more about the Pitch In for the Future Capital Campaign.