SUFFIELD — As McKenna Sherry made the long walk across Suffield Academy’s Rachel Carey Softball Field for the Tigers’ final postgame meeting of the season, the tears simply wouldn’t stop flowing.
She hugged her teammates, some of whom she would never play alongside again. She sobbed as she fell into the arms of her mother. She embraced Tigers head coach Patrick Booth, who is retiring after 25 years at Suffield Academy, 14 of which were spent as the school’s head softball coach.
When you care as much as Sherry does about this game and the people who play it, one thing became crystal clear in the aftermath of Suffield Academy’s 8-5 defeat to Cushing Academy in Sunday’s Western New England Prep School championship game.
Heartbreak doesn’t care what uniform you’re wearing from year to year. The tears will roll down the cheeks and splash onto the fabric whether it reads “Warde” or “Tigers.”
Heartache doesn’t care what league you’re playing in when you lose your final game of the season, be it a CIAC semifinal or a prep school championship game.
And in that moment, as the 16-year-old reclassified sophomore stood surrounded by a season’s worth of memories, and once again one final painful defeat, perhaps the most remarkable part of Sherry’s story came into focus.
Less than a year ago, she walked away from home.
Not forever, of course. But for a teenager from Fairfield, leaving behind Fairfield Warde High School, lifelong friends, familiar hallways, the Mustangs program, and the comfort of home to attend a boarding school near the Connecticut-Massachusetts border represented something far bigger than changing softball teams.
It meant changing her life.
“It was definitely nervous,” Sherry said. “But I think I knew with how ambitious I am to achieve my goals and stuff to play college softball, I think I knew that coming here would be the biggest thing that would help me get to that point.”
That ambition came with sacrifice.
At Warde, Sherry likely would have entered this spring as the Mustangs’ starting pitcher, competing in the pressure cooker that is Fairfield County Interscholastic Athletic Conference. She already knew the landscape. The FCIAC is a softball universe unto itself, where every game feels wrapped in expectation and every postseason run echoes through town.
Last season, Warde lost in the Class LL semifinals, on a controversial call at home plate; the kind of call and kind of loss that triggered the tears mixed with anger and hurt.
Once those tears dried up, however, Sherry took a long, hard look at her future. Then, she made a choice that many adults would struggle to make, let alone a teenager.
She reclassified academically, essentially repeating sophomore year to gain an extra season of physical development and recruiting exposure, and enrolled at Suffield Academy.
“Repeating sophomore year definitely wasn’t very fun,” Sherry admitted with a laugh. “I have another year of high school on me, but again, I think it just gave me an extra year for recruiting, gave me an extra year to get stronger, throw more, learn more stuff. So I think definitely it was a no-brainer.”
No-brainer or not, it still required courage.
There are romanticized versions of prep school life painted in brochures and social media videos. Then there’s the reality of a teenager learning how to live away from home while balancing academics, athletics and the emotional grind that comes with chasing lofty goals.
Especially for an only child.
“Having a roommate and everything, it’s a huge thing,” Sherry said. “But it’s really fun. The community here is amazing. You’re just always supported all the time. The school also has so many resources so you feel supported. There’s such a strong sense of community.”
And perhaps more importantly for a driven athlete like Sherry, there are very few distractions.
“There’s always something to do,” she said. “Whether I’m in the weight room, whether I’m pitching, throwing a bullpen, in the dining hall getting another meal in, in classes, at study hall. There’s always something to do.”
That structure helped transform her.
Sherry said one of her primary motivations for transferring was the opportunity to physically develop in a way she simply couldn’t before.
“I think definitely you could see my main risk for coming here was just to prepare myself and give me an extra year to get in the weight room more, eat better. The dining hall’s great,” she said with a smile. “I think what happened this season was exactly what I wanted.”
And it showed.
Booth, whose career at Suffield spanned a quarter century, immediately saw both the talent and personality Sherry would bring into the program.
Suffield catcher Carline Martorelli already knew Sherry through softball circles, helping connect the Tigers coaching staff to the pitcher before she ever arrived on campus.
“She’s a wonderful kid,” Booth said. “We knew we needed another frontline pitcher for this year. She was clearly a phenomenal athlete, but more importantly, she was just a great kid and leader.
“You could see that she’s vibrant and every day she just keeps everybody going and that’s what our community is about.”
For Booth, Sherry checked every imaginable box.
“She filled so many boxes for us on top of being just a top line pitcher,” he said. “I knew we’d have a top line pitcher for the year and we had three or four other good freshmen coming in, so I knew this year would be special and it absolutely has been.”
The season didn’t begin looking special.
Suffield opened its year with a rocky trip to Florida during spring break, a stretch Sherry described bluntly as “an absolute train wreck.”
“We were all nervous for how the season was going to be,” she said.
But somewhere along the way, the Tigers found themselves.
The chemistry hardened. The confidence grew. And Sherry became one of the emotional engines driving the team.
On Saturday, Sherry pitched a brilliant shutout win over second-seeded Choate Rosemary Hall, giving up just two hits and striking out 11 while walking two in a 4-0 victory that put the third-seeded Tigers into Sunday’s title game.
Sunday’s defeat left Suffield Academy with a 14-3 record and while the loss hurt, the memories will be there forever.
Sherry spoke glowingly about the bonds formed inside the program, especially with the team’s senior leadership group.
“It’s such a family,” she said. “Every practice, every game, every time we eat dinner together, every bus ride, I’ll always remember it.”
That family atmosphere made Sunday’s loss all the more painful.
The tears after the game weren’t just about a scoreboard. They were about finality.
For Booth, retirement had arrived.
For seniors, careers had ended.
And for Sherry, the realization hit that despite all the difficult decisions she had already made, none of them insulated her from sports’ oldest truth: eventually, every season has the potential to break your heart.
Some years it’s Ridgefield. This year it was Cushing Academy.
Yet even in defeat, there was validation.
Suffield proved it still belonged among the region’s elite prep programs, something Sherry admitted surprised her when she first entered the league.
“I was very surprised,” she said. “These teams are actually way more competitive than I thought they’d be.”
Coming from the FCIAC, where softball powers like St. Joseph, Trumbull, Darien and New Canaan annually create one of the deepest conferences in New England, Sherry expected prep softball to represent a step down competitively.
Instead, she found parallels.
“You have teams like Choate and KO (Kingswood Oxford) that are just like the Trumbulls and New Canaan and St. Joe’s,” she said. “Honestly, I’d say it’s pretty even.”
That realization only reinforced her belief that she made the right choice.
And maybe that’s the part adults sometimes underestimate when discussing ambitious teenage athletes: A kid deciding what version of themselves they want to become.
Sherry chose discomfort.
She chose an extra year of high school when many athletes would desperately want to graduate alongside friends.
She chose a weight room over familiarity. A dorm room over her childhood bedroom. Opportunity over comfort.
And standing there on Carey Field on a sun-splashed Sunday afternoon, tears streaming down her face after a championship-game loss, there was perhaps no clearer proof that she fully invested herself into this new life.
The uniform changed.
The commitment hasn’t.
Neither did the love for the game.
Growing up in Fairfield County, Sherry said softball initially stood out because it felt different from the sports culture surrounding her.
“Everything else is so heavy on soccer and lacrosse,” she said. “But I remember being younger, I just wanted to start Little League and I just fell in love with it.”
That love deepened thanks to countless hours spent working alongside her father and eventually evolved into pitching, where she discovered she enjoyed the pressure and responsibility that came with controlling the game.
“I like being a part of every play,” she said. “I just like having that sort of control on the field, like strong sense of leadership in the circle.”
Leadership. Responsibility. Sacrifice.
Those words followed Sherry long before she arrived at Suffield Academy.
Now they define who she is becoming there.
And despite the tears and hurt from this Sunday afternoon, despite the aching finality of one season ending, Sherry walked off the field with something far more meaningful than a trophy.
Proof that betting on yourself can hurt sometimes. But there is also proof that it can also be worth everything.
(From The Dugout is a regular column written by CT Softball Blog Publisher John Nash)
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