Samantha Simpson Awarded Pennypacker Prize

The Pennypacker Prize is a special way for us to recognize a Winsor teacher of great promise. 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.” Henriette attended Wheelock College after graduating from Winsor and went on to earn her M.Ed. from Harvard. A fervent advocate for women’s rights and environmental preservation, she loved classical music, dragonflies, and mid-coast Maine, and was described as having a “sense of absurd humor.”  The Pennypacker Prize is awarded each year to a teacher who is in at least their third year of full-time teaching at Winsor. It’s intended to encourage the recipient’s continuing educational growth and development. This year’s winner joins impressive company: our list of past recipients includes Josh Constant, Theresa Evenson, Jeremy Johnson, Maren Kelsey, Denise Labieniec, Andrew Marshall, Dana Martin, Ken Schopf, and Lisa Stringfellow, to name a few. 

The following award presentation—which remains a surprise until awarded!—was given by Head of School Sarah Pelmas during the faculty, staff, and trustee dinner on Tuesday, December 5, 2023, and announced to students during all-school assembly on Thursday, December 7, 2023.

Ms. Pelmas’s remarks are excerpted below: This year’s recipient arrived at Winsor in the fall of 2019 (remember the spring of 2020? Me either.), so she is in her fifth year, but Winsor has not been the same for any two of those years! Given the near constant changes and disruptions in her own life and in the world, I don’t think any of us could have expected the incredible brilliance and creativity she would bring to her classes, and to her students’ experience, all the time. 

Ask anyone what they think of this teacher, and you will get an observation like this one from Upper School Head Kim Ramos: “She is very honest and direct in her feedback, but in such a loving way that it is willingly and positively received.” Interim Upper School Head David Griffin remarks that “[her] wit is among her secret weapons as an advisor, just as it is in the classroom. She can tell advisees hard truths without their realizing that’s what’s happened because the feedback was delivered with such humor; still, they get the message. And they know they always have [her] support, even when they’ve made a mistake. There’s a reason [she] is such a popular advisor with kids and their parents alike.” 

When I reached out to English Department Head Courtney Jackson to ask for a little overview of this teacher’s work here, I got an extraordinary encomium that I want to read almost in its entirety, because it’s so comprehensive and specific. “[She] is a calm, steady presence who brings a creative perspective to the department and a playful pedagogy to the classroom …. Rather than teaching grammar from a boring stand-alone textbook, she creates lessons that connect the concepts to their reading or the real world. A staple of her classroom is ‘Girl Group Grammar’ which involves using the music of girl groups, past and present, to locate grammar concepts. Holden! The Musical follows up on these lessons and asks students to become a “mid-century girl group to write and perform a song about Holden Caulfield’s experiences using meaningful adjective and adverb clauses while discussing what has happened in Salinger’s novel so far.” She has students decorate old-school composition notebooks and calls them ‘Daybooks.’ They use them daily to record their reflections about the reading. She creates fun routines in the classroom, like her ‘hijinks’—as she calls activities that require kids to get up and move around the room—decorating the board or posters with imagery from Their Eyes Were Watching God or creating tableaux from Romeo and Juliet. In another lesson during our Harlem Renaissance unit, she creates stations around the room and has students visit them in small groups—listening to music from the period in one corner, viewing art in another, reading poetry in another….She has [brought] intellectually rigorous and fascinating electives to our seniors—including her popular Afrofuturism course, in which she excites students about her own favorite literary genre and her fall elective called ‘Defiance of the Creator’ in which she proves to kids that they can indeed tackle texts, like [Milton’s] Paradise Lost, that at first seem indecipherable.” English teacher Ned Henningsen adds to this overview, writing, “Here’s just the tip of an iceberg: Whereas the header for my lists of essay topics would read, very creatively, ‘choose your essay topic,’ [she] would frame hers like characters in an arcade game: ‘Choose your fighter.’ Her students know that their essays need to be engaging enough to compete with watching episodes of Buffy the Vampire Slayer. For ‘girl group grammar’ exercises they have to break down the grammatical structures of lyrics from such illustrious ensembles as The Spice Girls, En Vogue, Sister Sledge, and Bananarama. For Their Eyes Were Watching God, [her] students ‘film’ an episode of The Real Housewives of the Everglades, taking on the personas of different characters and discussing the drama that goes down in various scenes—‘Rumble at Mrs. Turner’s Restaurant!’—just like the talking heads in the show. The directions emphasize that they ‘have to make sure to bring the drama,’ and oh boy, they do.” 

Andrea Chase encapsulates all this beautifully when she says, “Staunch Buffy defender, inventor of the girl-band grammar test, and wearer of a pink, leather power suit, [she] brought a whole new level of flair to the English Department when she came to Winsor! She is wonderfully imaginative in how she designs her courses, and working with her is a reminder not only that it’s okay to think outside the box but also that sometimes you really must blow up the box entirely.”

This teacher makes Winsor a wonderful place to work for her colleagues as well. English department colleague Laura Krier has said that she is “here at Winsor in part because of [this recipient]. The day I interviewed,” Laura says, “I met the department over lunch, and—knowing [this teacher] was new to Winsor—I asked her how her year was going. Her enthusiastic response told me a lot about Winsor’s culture (she said something like ‘I’ll never leave; they’d have to pry me out of here’).”

Banner co-advisor Erin Cantos tells a story about going to the Salem Witch Museum together with this teacher, then gushes: “It is folks like [this teacher] that make Winsor such a magical place to work.”
Students love her, with just the right balance of awe and hero-worship. They routinely comment about how life-changing her classes are for them, as does student Sophia Lichterfeld ’24 when she says, “[This teacher] truly makes every student genuinely excited each day in class. At Banner meetings, she is eternally supportive, and she makes layout days go by really quickly with her humor, dedication, and insight.” Banner editor Suzanne Pogorelec ’24 adds, “During layout and editing week, her suggestions are firm yet thoughtful and through every comment she continually pushes us to write pieces that are truly meaningful to the Winsor community, ones that make students proud to see their name in print.”
Senior Alyssa Quarles ’24 says, “That she allows us to defy some of the constraints of our assignments as long as we “eat with what we write,” as she often says, is quite fitting for our class, Defiance of Creator. I appreciate that this practice lets creativity flow and allows students to take risks in their work.”

And Class VIII’s Vanessa Paige ’24 comments, “She has such a unique and charismatic teaching style full of millennial humor that never fails to make any activity epic…Her greatest impact on me, however, stems from the many trips to her ‘Tea Room,’ a place where she shares all of her current reads; I can confidently say that [she] has single-handedly fostered and fueled my addiction to romance novels, and for that, I am forever grateful.”

From our own Theater Tech intern and Winsor alum, Brianna Feliciano ’20: “Overall, [this teacher] inspired me to be badass and my authentic self.”

This year’s winner is creative, joyful, inspiring, and an incredible cheerleader for students while holding them to very high standards. Please join me in congratulating this year’s Pennypacker Prize winner, Ms. Samantha Simpson!