Berkshire’s path to an undefeated Evergreen League title wasn’t paved with easy wins; it was carved through hard-fought, high-pressure battles that demanded grit, composure, and unity.

“We were in tons of close games,” Head Coach Tim Cary said. “Our guys never gave up. They stayed together, lifted each other up, and didn’t point fingers. That was the biggest factor in our success.”

Quarterback Levi Altshuler ’26, in his second year with the Bears, felt the shift this season immediately.

“This year we were so close as a team, on and off the field,” Altshuler said. “Football meant more to us. We wanted to win for each other. No one got jealous, and everyone just wanted their teammates to succeed.”

That connection carried the Bears to an 8-1 overall record and a New England Preparatory School Athletic Council championship, culminating in a dramatic nail-biting 14-13 victory over Noble and Greenough in the Bob Souza Bowl––a rematch against the only team that beat them during the regular season.

The Bears’ success this fall was fueled by a strong group of upperclassmen who set the tone daily. Their leadership showed up not only in big moments on game days, but also in smaller, telling ones––like standing on the sidelines at junior varsity games.

Altshuler and Benjamin Kennedy Chaanhing ’26, in his first season at Berkshire, spent the program's only junior varsity home game on the sideline guiding and encouraging their younger teammates.

Altshuler also built a close friendship with junior quarterback Harry Stournaras, spending time passing together during the offseason and making sure to attend dinners as a pair, fostering team chemistry off the field as well.

These off-field bonds reflected the team’s larger spirit: everyone contributing to everyone else’s growth.

For Cary, it was a defining snapshot of the team’s identity. 

“That’s who we are,” Cary said. “Those JV guys give us great looks all week to prepare our starters. Supporting them is the older players’ way of returning the favor. Every role is different, but every role is important.”

Freshman Brodie Bowler ’29 said he felt that mentorship from day one.

“The older players have been super supportive,” Bowler said. “They cheer me on and teach me how to improve. The chemistry on the team made a huge difference this season.”

Kennedy Chaanhing, coming from Sweden, experienced that same culture despite being new to Berkshire.

“From the start, everyone welcomed me,” he said. “I felt like I belonged right away. I wanted to work hard because everyone around me was working hard too.”

The team’s only regular-season loss came at home to Nobles on Fall Family Weekend––a narrow 28-24 setback that could have derailed a lesser team. Instead, it became fuel.

And while players were excited for a second chance, Cary and his staff––assistant coaches Mike McCabe, Justin Torre ’07, Brian Rodriguez ’16, and Alex Barnosky ’19––kept the team grounded in routine rather than revenge.

“We prepare every week like it’s the biggest game,” Cary said. “We didn’t want to get caught up in emotion. We focused on our normal structure––film on Monday, defense on Tuesday, and so on. The players bought into that.”

The disciplined approach paid off. In a gritty, physical bowl matchup, the Bears executed when it mattered most. The game’s decisive moment came in the final minutes, when Scout McKnight ’28 intercepted a pass with less than two minutes remaining, preserving the one-point lead and helping to secure the program’s first Bowl win under Cary.

For Cary, now in his fourth year at Berkshire, the significance of the moment was deeply fulfilling. Berkshire hadn’t won a bowl game since 2017, when the Bears defeated Buckingham Browne & Nichols School 35-28 in the Hugh Caldera Bowl under then-head coach McCabe.

“Two seasons ago, we didn’t win a game,” Cary said. “Seeing these kids stick with the program and build it into the team they are now… Seeing their faces and the joy they felt, that’s what made this season so memorable.”

That group included four-year players like Mo Amin ’26 and Westley Hampton VanSant ’26, along with a talented mix of postgraduates whose maturity, competitiveness, and buy-in elevated the team from the moment they arrived.

Cary believes the program's progress reflects something larger about the Berkshire community.

“When new student-athletes come here, they’re welcomed right away,” Cary said. “This was a really unique group, and now with a lot of players graduating, the next adventure is finding the next wave and recruiting players who want to be part of it.”