Trey Whitfield ’89 dreamed of one day having an impact on kids’ lives. Over three decades, his parents—and Brewster—have worked together to make those dreams come true, turning tragic loss into a legacy of opportunity.

Words by Jim Collins
Photos by Rob Bossi

In May of 1989, just days before he would have graduated, senior Trey Whitfield died in a drowning accident on a small lake a few miles north of Wolfeboro. For the Brewster community, the sudden loss was not only tragic but unfathomable. Trey was an immense life force on campus: adored, goofy and gregarious, big-hearted, a hugger, with the kind of presence that commanded a room while making sure there was room for everyone around him. He was a six-foot-eight, 240-pound power forward and most valuable player on the school’s New England champion basketball team, headed for the University of Richmond on a full scholarship and dreams of a career in the NBA. He planned to someday work with kids.

He had come to Brewster as a sophomore, arriving late to his dorm room after his roommate, Mike Clark, was already asleep. Clark heard the knock on the door, jumped out of bed, and threw on the tan bathrobe his mother had packed for him back in Maine. Without pausing to introduce himself, Trey said, “Man, that is one ugly bathrobe,” and the two of them exploded in laughter and became fast friends. He got his reluctant teammates to act in the school musical “Damn Yankees,” and they had the time of their lives. 

His death stunned the campus. Teachers and students, hollowed-out and red-eyed, wobbled through the following days. As history teacher T.J. Palmer later wrote:

We were numb. Sadness enveloped us, took our appetites away, and sapped our energy.

As faculty, we had no answers for all the students who continued to ask “why?”

Then, Palmer recalled, A.B. Whitfield, Trey’s father, arrived on campus. At a school gathering in Wolfeboro’s Congregational Church, where faculty, staff, students, and alumni packed the pews, Mr. Whitfield took the podium and, in Palmer’s words, “commenced to heal us.”

He stated very clearly that he had come to heal us. He stated that he loved us and that he knew how hard Trey’s death had been for us. He thanked Headmaster David Smith Coach Bolduc, the faculty, the students, and the staff for all they had done for his son. He talked about how much Trey had loved his school. He told us that it had been a privilege to share this earth with his son for 18 years. He told us it was okay to cry. 

In that moment of grace and deepest grief, a relationship of extraordinary power took hold.

A.B. Whitfield had played in the NFL with the Dallas Cowboys, Washington Redskins, and Denver Broncos. Following his playing career, serving in New York City’s troubled public school system as an educator and a volunteer, he had become disenchanted working with people who, he said, “weren’t geared to helping children every day.” It was his wife, Janie Whitney, who had the idea of starting an independent school that would do things differently. A Brooklyn native, Whitney left a career in finance to found Bethlehem Baptist Academy in East New York, one of the borough’s toughest, most underserved neighborhoods. “I believe all children can learn,” Whitney has said in many interviews through the years about the success of the school—it is one of her most fundamental guiding principles. 

The K-8 school, taking its name from the owners of the building it occupied and mirroring the demographics of the neighborhood in 1983, enrolled students who were overwhelmingly below the poverty line. The school required uniforms and good conduct and imposed discipline. It had high expectations for its students—including the presumption that kids could learn to read even as early as kindergarten. At first, A.B., exhausted and disillusioned from his public school experience, helped on the fringes: reviewing the curriculum, for example, and stepping in as a math and gym teacher early on when the school was searching for educators to fill those positions. Together, the couple poured themselves into the school, and grew its reputation for excellence with utter devotion.

Alongside Janie, who received awards for her work as an educator and as a positive force to be reckoned with in the community, A.B. brought his immense life force to his role. He hugged the kids, especially the boys, so they would know that it was okay to be gentle. He made sure the school felt safe—that it was a sanctuary. During snowstorms, while other schools closed, he slept at school so he could open the doors the next day, knowing the kids wanted and needed to be there. “God gave me one gift that I know of,” he would say. “Not athletics. Just the gift of winning children over. I can look into young people’s eyes and say, ‘I love you,’ and they deeply believe it. I know I can help and serve children. They respond to me because they can feel that. They know it’s from my heart.” The school quickly distinguished itself as an anomaly among New York City schools. Many of its students performed two and three years above grade level on national achievement tests. Trey was the first of its students to attend Brewster Academy.

After Trey’s death, A.B. and Janie changed the name of the school to honor their son, and regularly returned to Brewster to attend the annual lecture that the school hosted in Trey’s memory, often bringing with them the student choir from their school in Brooklyn. The Trey Whitfield Memorial Lecture was scheduled each year around the Martin Luther King Jr. holiday. The timing was a nod to those qualities in Dr. King that Trey had also exhibited during his lifetime. At the 20th annual lecture in 2009, A.B. delivered the featured remarks. He reminded the community of the event’s other connection to the MLK holiday: “History was made on this campus 20 years ago,” he said, “when a group of Brewster students led by Trey and [former teacher] Tim Radley ‘stormed the capitol’ of New Hampshire to insist that the state recognize and celebrate Dr. Martin Luther King Jr. Day, which proved successful.” 

The lectures were often emotional. One year, Trey’s classmate Todd Parola said that he’d drawn on the strength and inspiration of A.B. and Janie when his brother Jeffrey, a Maine state trooper, was killed in the line of duty. Teammate and close friend Curtis Nelson shared that he’d named his son after Trey. 

The annual lectures also provided a natural occasion for students from Brooklyn to visit a private school in rural New Hampshire, to give them a glimpse of an educational opportunity far beyond their normal daily experience. (Tim Radley and his wife, admissions associate Peg Radley, along with other faculty, welcomed students into their home during the lecture each January for 18 years, until Peg’s retirement.) Since the time of Trey’s death, the Whitfields’ school has been sending a student or two each year to join Brewster’s incoming class. For years,  Janie worked directly with Brewster’s Admission Office to ensure that students would be the perfect fit and thrive here. She took immense care in selecting students who would be good role models. “There are six or seven private schools our kids go to,” said A.B. “For lots of reasons, Brewster is Number 1 on the list. At Brewster there are standards. There are expectations not only for academics but for social skills and acting as productive members of a community. That’s a direct match with us. We share a philosophy.” 

Brewster provides most of the necessary financial aid—and some comes from the Trey Whitfield Foundation, a nonprofit A.B. and Janie created in 1989 “to commemorate the life and spirit of Trey Whitfield.” In his memory, the Foundation’s mission states, it “will pursue his dream that everyone, regardless of ethnic background, has equal access to the educational opportunities that they need to reach their potential in life.” Each year, the Foundation holds a black-tie fundraising event where positive, productive, inspiring community members are formally recognized. Annually, a Brewster trustee or staff or faculty member is among the honorees. 

During the 2004-05 school year, A.B. and Janie’s school moved into a new five-story building, and changed its name to Trey Whitfield School. The relationship between the Whitfield family and Brewster continued to deepen. In 2014, on the 25th anniversary of Trey’s death, Brewster renamed its annual winter basketball tournament the “Trey Whitfield Invitational,” and another touch point was created. A framed basketball jersey bearing Trey’s #34 was created to permanently honor Trey’s connection to Brewster’s basketball program—his 1988 team had won the first New England championship in the school’s history; in the ensuing years the program evolved to the point where it was using national championships as a measure of its success.

A duplicate framed jersey was presented to Trey Whitfield School, where it remains on display as a reminder of the person whose name the school bears.

In the Spring of 2017, Brewster’s Director of Equity and Inclusion programs, Melissa Lawlor, set the gears in motion for an even more intimate connection between the two schools. She suggested a project-based learning experience for Brewster seniors that included serving as mentors for seventh and eighth graders from the Trey Whitfield School. That senior project quickly evolved into a formal program involving 12 students from each school with four face-to-face mentoring and discovery opportunities throughout the year. The Brewster students get to visit the Brooklyn school and homes of the Trey Whitfield students; the young students from Brooklyn attend the Trey Whitfield Invitational tournament at Brewster, stay in the dorms, and get a tour of campus. At Camp Jewell in Colebrook, Connecticut, the students get together for games and trust-building activities, and stay overnight together in a giant bunkhouse. For many from both the schools, the program provides a first deep experience with people of a different racial or economic background. This past year, A.B.’s god-daughter, Jaila Richard ’22, served as one of the Brewster mentors.

Some of the mentees, exposed to Brewster as middle schoolers, will go on to Brewster and cement the relationship still further, adding to the almost 50 Trey Whitfield School alumni who have attended Brewster over the past quarter-century, enriching the community with their diversity of experiences and viewpoints—and who have gone on to fine colleges and successful careers in education, business, engineering, and law. The most recent Trey Whitfield School alums to graduate from Brewster include Shemar Joseph ’19, Trinity Towns ’19, Indigo Brown ’20, and Jawan Lawson ’20. After graduation, Joseph headed to Boston College, Towns went to North Carolina A&T University, Brown moved west to attend the University of Chicago, and Lawson headed to Massachusetts to begin his college career at Tufts University. 

The legacy created by A.B. and Janie, started before their son’s passing and bolstered by his memory, is powerful, yet the couple are humble. After being named one of Brooklyn’s “Women of Distinction” in 2011, Janie said, “If I can help somebody as I pass along the way, my living will not be in vain.” This sentiment, just as true now as it was then, is shared by Brewster, where we know education transforms lives.  

“Brewster Academy meant so much to Trey,” says A.B. “And so much to our family. To keep that flame alive, keep Trey’s legacy alive… I can’t tell you how important that has been to me. To have an ongoing connection with the school that Trey loved so much has helped ease the pain of the loss of our son. Brewster is deep in our hearts.”

The healing has gone both ways.

FOR MORE INFORMATION about the Trey Whitfield School, visit treywhitfieldschool.org. And to learn more about the important work of the Trey Whitfield Foundation, visit treywhitfieldfoundation.org.