Erin Cantos Wins the Pennypacker Prize

The Pennypacker Prize is awarded each year to a teacher who is in at least their third year of full-time teaching at Winsor. Created in 2002, the award is “given annually in the name of Henriette Pennypacker Binswanger ’52, with respect and admiration for the educational excellence of the Winsor School and the memory of an extraordinary experience.” As is tradition, the recipient is kept secret until the final moments of the presentation at the annual, with clues woven into the speech and speculation rippling through the audience—including, of course, the eventual winner.

This year’s Pennypacker Prize was awarded to History Faculty Erin Cantos, and as Head of School Meredith Legg began her speech, many in the room quickly recognized the teacher being described. “This year’s recipient,” Ms. Legg hinted, “is someone whose intellect is matched by her warmth, whose rigor is matched by her joy, and whose enthusiasm for her subject could make even the most reluctant student lean in.”

From the moment Ms. Cantos arrived on campus, colleagues sensed something special. Ms. Legg recalled an early conversation that left Institutional Researcher and Science Faculty Denise Labieniec thinking, “Now I completely understand why everyone is so excited about her coming to Winsor!” Ms. Cantos, Ms. Legg noted, is the rare educator who combines deep expertise with what she called “joyful geekery”—the ability to transform a casual exchange into an intellectually rich and energizing experience.

A gifted historian and devoted teacher, Ms. Cantos is known for her creative, student-centered instruction and her unwavering belief in her students. English Department Head Courtney Jackson, who worked closely with Ms. Cantos on the Indian Global Studies course, described her as “a fabulous, open-minded collaborator,” noting that Ms. Cantos brings her “warm, supportive, inquisitive, energetic persona” to her work with students. Ms. Jackson added, “She has high expectations for them, and she is not afraid to give them direct feedback, but they also know that she cares about them and believes in them.”

Ms. Cantos’s classrooms are animated by curiosity, humor, and intellectual rigor. Her use of memes, Ms. Legg shared, has become “almost legendary,” sparking laughter while making history feel immediate and alive. Beyond the classroom, Ms. Cantos is a devoted advisor to The Banner, where she works closely with students to help them cultivate their voices as journalists and citizens of the world.

Ms. Legg also highlighted Ms. Cantos’s close partnership with English Faculty and Banner Co-Advisor Samantha Simpson. She shared Ms. Simpson’s recollection of knowing almost instantly that Erin was “a shoe-in,” explaining, “A person can’t be that enthusiastic and joyful about history and education and not get the job.” Reflecting on their shared work, Sam added, “I am grateful for every minute that I’ve worked with Erin,” ultimately describing her as “my friend, my sweatshirt twin, my sister.”

In closing, Ms. Legg captured the spirit of the evening—and the award itself—by noting that Erin Cantos “embodies all that the Pennypacker Prize is meant to recognize.” Through her scholarship, teaching, collaboration, and care for students, Erin makes Winsor wiser, warmer, and more joyful each day.