The CT Softball Blog

TRUMBULL—Madison Pippa considers herself a goal-oriented person.

Set a goal, work hard for it, and find a way to succeed.

When she was just 7 years old, however, Pippa wondered if she would ever become a successful softball pitcher.

“When I was 7, I wasn’t sure I could achieve my dream of being a softball pitcher because I was small, but with hard work and support, I never gave up—and now that dream is real,” Pippa said. “I can’t imagine my life now or in the future without softball.”

She doesn’t have to.

Despite still being a bit under-sized, at 5-foot-1 (in cleats), Pippa stands tall in the circle as the starting pitcher for Trumbull High School.

And, even as she graduates following her final season at Trumbull later this coming spring, Pippa’s softball career is still far from over.

In fact, after flying so high as an Eagle, Pippa will continue to try and soar as Seahawk, after committing last year to keep her career going at Wagner College.

“I’m excited to be a part of a growing program focused on building a strong, positive team culture,” Pippa said of what drew her to Wagner. “I’m looking forward to being part of something special on and off the field.”

Pippa said she liked Wagner’s small class size—“It’s a Division 1 program with a small-school feel,” she said—and likes the hands-on learning style that fits her learning process.

While she looked at schools at each level of play, Pippa’s competitive nature did draw her to look more closely at some Division 1 schools.

“I’ve always dreamed of playing at the highest level and testing myself against the best players in the country,” Pippa said. “During the recruiting process, I kept an open mind and looked at schools from all levels. My pitching coach encouraged me to think about where I could see myself even without softball, and Wagner was that school. It checked all the boxes both on and off the field.”

Life without softball, however, is hard to imagine.

Pippa has always loved sports and played multiple ones growing up in Monroe.

In eighth grade, though, she really started to put more focus and effort into the sport.

“I started focusing more on pitching and committed to softball,” she said. “I love the intensity, the pace, the teamwork and the challenge. I was always throwing and hitting. It just felt right.”

Despite never being the biggest pitcher in the dugout, Pippa also decided to never let her size become an issue.

“Pitching has always excited me because of the responsibility it brings,” she said. “I love being in control of the game and setting the tone. I enjoy the pressure and the challenge of big moments. Being in the circle pushes me to stay focused and confident. I thrive on competition and the chance to make a difference every pitch.”

When she was 7 and felt those first twinges of doubt, Pippa was playing for the Monroe Mustangs.

When she was 10, she helped lead Monroe Little League to its District championship and the state tournament.

“Early coaches helped foster my love of the game,” she said.

Soon enough, Pippa joined the travel ball ranks, joining the CT Seahawks program in middle school. Even after the Seahawks were bought out by the Rhode Island Thunder, Pippa remained with the organization.

She remains with them, playing for the RI Thunder 18U team.

It’s been a journey leading her up to one last season as a Trumbull Eagle.

Last season, as Trumbull’s starter, Pippa pitched a senior-less Eagles squad all the way to the FCIAC semifinals.

“At just five-feet tall, Madison Pippa has spent her life defying expectations,” said former Trumbull coach Jacqui Sheftz, who stepped down after last season. “Fueled by a deep love for the game, and an unmistakable drive to prove the doubters wrong, she turned every ‘too small’ into a reason to work harder. Now, as a Division 1 softball commit, Madison isn’t chasing her dream, she’s living it.”

This season, Pippa just wants a strong finish to her high school career.

“I want to help the team build on last year’s success,” she said. “Stay competitive throughout the season, make another strong run in the FCIACs and states, and just grow together with a new coach and a young roster.”

Then comes college, and the next chapter of her life and career at Wagner, where she hopes to major in Health Sciences and become an athletic trainer or physical therapist to help a new generation of athletes to reach their goals.

“I really admire the trainers at Trumbull High School — they’re always there for me and have helped me tremendously,” Pippa said. “My physical therapist has also made a huge impact, working with me through a few injuries and making a big difference in how I feel physically. Their support has inspired me to help other athletes the same way.”

Wagner will be the place for her to start that journey.

“As a college player, I want to take all the life lessons I’ve learned as a player and teammate with me, and continue to grow both on and off the field to be the best I can be,” Pippa said. “I strive to be the best teammate possible, make an immediate impact, help my team succeed, and represent my school with pride.”

Pippa also knows she hasn’t made the journey alone, filling in a line-up of coaches who have helped make it all possible. From Kelly Pietro (T-ball) to Ron Rogg (Little League) to Dave Lotti and Frank Lieto (CT Seahawks/RI Thunder) to Coach Sheftz, Jen Russell (her first pitching coach) and Jen Happanowicz (her current pitching coach), Pippa has been built under their tutelage.

It took another coach, Glen Moore at Wagner, to recognize all that.

“(Moore) didn’t overlook me because of my height,” Pippa said. “All these coaches believed in me and helped me to never give up on what I love to do.”

Madison Pippa overcame her moments of youthful self-doubt to find herself as the Division 1 pitcher she dreamed about becoming.

So that’s four more years of softball and playing the game she loves.

“Softball means so much to me,” she said. “It’s where I’ve made great memories and learned important lessons like discipline, teamwork, and resilience. I’ve grown as a person and built confidence that extends beyond the field.”

Love Stories Like This?

Get Connecticut’s best softball features, breaking news, recruiting updates and exclusive interviews delivered to your inbox every Friday morning. Subscribe to the CT Softball Blog Weekly.