Assistant Head of School for Enrollment, Strategy, and Athletics
University of Massachusetts at Amherst; BA; Amherst, MA
Subject Areas at Winch:Assistant Head of School for Enrollment, Strategy, and Athletics, CoachPhone: 978-297-7904
The name John Toffey may be familiar to hockey fans. John was drafted by the Tampa Bay Lightning and played professional hockey for three years. These days, John is known as a New England boarding school admissions professional. At The Winchendon School, in his role as Assistant Head of School for Enrollment, Strategy & Athletics, John heads a team of four admissions representatives and staff. In addition, John, who was selected in the Major League Draft by the Colorado Rockies and played baseball at the University of Massachusetts at Amherst, is the Head Varsity Baseball coach at The Winchendon School.
“The Winchendon School is poised to attract great students. From the moment I stepped onto campus, I was struck by how happy the students, faculty, and staff were. Unique academic programs: Global Dynamics, CoLABs, and Service-Learning coupled with small class sizes are differentiators for The Winchendon School. Beautiful facilities and welcoming faculty are a testament to the culture of the school.”
As the Varsity Baseball Head Coach at The Winchendon School, John arrived with a prep school record as Head Varsity Coach of 135 – 9, John’s record speaks for itself. More impressive than the win/loss record is the amount of students who have continued their careers at top colleges and universities. Student-athletes he’s coached have gone on to compete at Vanderbilt University, Clemson University, University of Richmond, Harvard University, Stetson University, UMass-Amherst, UCONN, Dartmouth College, Northeastern University, Colby College, Boston College, University of Michigan, and Tufts University, among others. In addition, he has a history of coaching Major League Baseball draft picks, five of whom are currently in MLB spring training camps.
Since arriving at TWS, John coached his team to the Small School Championship as a winner and finalist three of the past four years (with a year off for Covid). Since 2019, over 50 baseball players have gone on to play in college with one being drafted by the NY Yankees.