Esteemed Leaders Deb Sampey and Shelley Greenwood to Retire


Annie Hallinan

Current Assistant Head of School Shelley Greenwood and Middle School Director Deb Sampey.

Middle School Director Deb Sampey and Assistant Head of School Shelley Greenwood will be retiring at the end of this school year. Both beloved members of the Latin community, Ms. Sampey and Ms. Greenwood will be dearly missed.

Former Latin parent Charlie Taylor said, “I think [Ms. Sampey and Ms. Greenwood] represent a great building of adherence to the highest educational standards you have with an atmosphere of kindness, generosity, and civility. Those two things created a unique environment. And they were leaders in that regard, in developing and maintaining those core values.”

In her 37 years at Latin, Ms. Sampey has fostered a rigorous academic curriculum that allows students to shift their focus from grades to deeper learning processes, promoting curiosity and emphasizing togetherness. She has also helped develop after-school athletic programs.

Reflecting on her time at Latin, Ms. Sampey said, “The aspect of my work that feels most transformational—and maybe I’m most proud of—is creating a distinct and separate Middle School.” By creating a distinct Middle School and moving fifth grade from the Lower School to the Middle School, students “could have a fuller academic program, but they could also have access to the co-curricular program,” Ms. Sampey said.

“When I first started working at Latin, the middle was actually in the high school building. The gym was on the fifth floor, but there were no classrooms, no hallways up there, nothing. The Middle School and high school shared the same classrooms. They shared all of the same spaces. The biggest move of all was getting a separate Middle School building,” Ms. Sampey noted.

“It’s just joyful working with [Middle Schoolers]. And I know they’re pack animals at times, but for me, it’s really the best stage because they still have some of the joy and wonder and lack of self-consciousness,” Ms. Sampey said. “They come in and they’re willing to be a little bit more playful, more silly, and they’re willing to go deeper into subjects. And they’re starting to develop their own identity and their own sense—their own opinions about topics, and their own perspectives. For me, the Middle School is a really happy place.”

Latin parent and Vice Chair of Latin’s Board of Trustees Dara Milner said, “Deb and I, we co-chaired the strategic design team that basically came up with the current strategic plan for the school, so that was a board-school collaboration. A couple of things I learned about Deb in that process is that she’s very good at taking a ton of data and analyzing it and synthesizing it and asking very pointed questions to come up with a solution that would impact all the communities.”

In her 30 years at Latin, Ms. Greenwood has served in many leadership positions. Though the Assistant Head of School role has been her longest, Ms. Greenwood also served as Interim Head of School twice and Interim Lower School Director for one year.

Ms. Greenwood said, “I started off in this area, we call it Enrollment Management now. It was called Admissions and Financial Aid at the time, and I was really excited to have the opportunity to expand the reach of the school into Chicago, which is coming from more than just this neighborhood.”

Among Ms. Greenwood’s impact in that role was her effort to expand tuition assistance to more than just the high school. “It took us a little while,” she said, “but eventually we started offering tuition assistance for kids as little as JK.”

Ms. Greenwood also commented on another of her greatest accomplishments: celebrating Latin’s 125th anniversary a decade ago. “I was proud of how we celebrated the 125th, that was kind of my responsibility. I had wonderful help with that,” she said. “But to have a year-long celebration that brought all aspects of the community together: alumni, faculty, families, staff, board—I think it was a terrific moment for us. Just to have the whole canvas of the entire year and to find different ways to brand it, it was a nice event.”

“I do think it was important to mark and to really reach back,” she said. “And the magazine we typically publish became the updated full history of the school. And it was a very transparent history—it talked about some of the rough times that we’ve had; it talked about some of the challenges as well as some of the accomplishments.”

Both Ms. Sampey and Ms. Greenwood noted that the people are without a doubt what they will miss most about Latin. “You know, the hardest part is—[Latin] is a relationship-based school,” Ms. Sampey said. “I have so many wonderful and fond memories and experiences with colleagues, but I also think [the same] of all of the kids over the years.”

Similarly, Ms. Greenwood said, “It’ll sound cliche, but all of the people. And that means all of you, my colleagues. I’ve had just wonderful people that I’ve worked with, all of these years, and they’re why I get up in the morning and come in. I do a lot with the Parent Association. They’re so critical for our success at the school. I’ll miss everybody.”

Former Latin parent Liz Taylor said, “I think they were wizards of melding sort of the old and the new, and that they represent some of the best values of academic achievement, and also a generosity of spirit. They saw students and staff and teachers as sort of whole people; they didn’t see them as in their particular roles. Individually, they each had a moral compass and used it to inform decisions about the community and building community.”

To students, Ms. Sampey said, “One piece of advice is to appreciate the opportunities that come with being a student in a JK-12 school. Where we can build content, not just cramming in all the skills and taking tests. I think that is just one of the real opportunities. My experience, both working here as long as I have and having two children who have been lifers JK-12 here, is that every division is so special. The differences are really in response to the developmental needs of the kids. The rigor is there at every age—the rigor is what happens every day in the classroom.”

“All the best to Ryan Allen,” Ms. Greenwood said of her successor. “I’m so excited to have a veteran educator from another highly regarded school, to have an alum of Latin, to have someone who already has a relationship to this place. I think we’re so fortunate.”

Asked what advice she would offer Latin students, Ms. Greenwood said, “Stay true to our mission, weather through challenging times—because the school has throughout the arc of its almost 140-year history now—collaborate and work together, listen to what each other needs, and try to keep the school [with] students at the heart.”

Ms. Sampey said, “I love this place. I’m leaving because it’s the right time for me to do something different, and it’s also the right time for the school. It’s time for someone with new opinions, new ideas, to come in and look at everything through a different lens.”