As I sit across from Director of Upper School Gary Baldwin in his office during our interview, I observe the many decorations I have seen before—the empty gumball machines, pictures of his young self and his family, and the rubber ducks that fill the office’s every crevice. This time though, as I realize this may be the last time I see the director of Upper School’s office dressed this way, I think of how each object on each shelf represents something different about his time at Westridge, rooted in his community involvement.

On January 6 of this year, Head of School Ms. Andrea Kassar announced to the Westridge community that Mr. Baldwin would be stepping down from his position as Director of Upper School. After nine years at Westridge, Mr. Baldwin is moving to Washington state to support his family members. 

After joining the Westridge community in 2015, Mr. Baldwin supported the school through the pandemic, the removal of APs, the revamp of Discovery Week, and more. His presence remained a source of support for students, faculty, and parents. To Mr. Baldwin, pinpointing one moment or initiative he is proud of is difficult. Rather, he said, it’s the smaller interactions with community members. “In the end, you really remember the opportunities that you’ve had to help teachers to support students. So the little things,” Baldwin said. Additionally, he spent several years teaching various classes at Westridge, from U.S. History to Economics. 

Mr. Baldwin noted that the decision to leave Westridge wasn’t easy. He said it was “without question the hardest decision that I’ve ever made in my professional life,” in a January interview with Spyglass editor Sophene A. ’25.

The decision comes with mixed emotions for Mr. Baldwin. He said, “I’m excited for what comes next, but Westridge has been my home and the people here have been family to me for the better part of the last decade. So it’s exciting to look ahead, but it’s also a pretty big change in my life.”

He continued to emphasize his love for education, and the students and teachers at Westridge. “Nobody takes a job like this unless they really care about schools, really care about teachers, really care about students,” he said.

He shows his care for the Westridge community in many ways, whether it be telling jokes at community gatherings, visiting U.S. history classes to talk about the Gettysburg Address, having slime poured on him for a fundraiser, or being on speed dial for dozens of faculty members. At the end of the day, Mr. Baldwin was there for all the moments—big or small—to support students and faculty whenever they needed it. 

Each and every student had a different relationship with Mr. Baldwin, some more serious, some more playful. For example, as mentioned previously, Mr. Baldwin’s office is decked out with rubber ducks. These small but bright toys are a student-organized initiative, a complete mystery to Mr. Baldwin. One day several years ago, Baldwin entered his office to find a couple of ducks on the shelves. Then, there were more ducks. And then, his shelves were completely covered. Mr. Baldwin has suspicions about the duck organizer, but said, “I like the mystery better than I like the solution.” He continued to say, “These are the kinds of things that you really love about schools.”

Just as Mr. Baldwin loves the community at this school, students and faculty mirror his appreciation, speaking highly of their experiences with him.

As a student in his Economics class this year, junior Emily Z. interacted more than ever with Mr. Baldwin and developed a love for his class. His teaching made her love the subject. “Taking economics was probably one of the best decisions I’ve made [this] school year,” she said. “Mr. Baldwin’s an amazing teacher and I love his humor.” She continued to speak for her class, saying, “We’re all extremely sad to see him leaving.”

Assistant to the Director of Upper School Ms. Ashley Leonard, who helps Mr. Baldwin with his schedule, organization, and student interaction, is also sad to see Mr. Baldwin leave. She said, “I’ve enjoyed my time working with him. He always has my back, helps me when I need help. I wish for him [to have] a stress-free environment with good vibes always.”

For now, Mr. Baldwin does not know much about what his future entails, but he does know he will always remember Westridge and the memories and experiences his time at the school brought him. “I’m certainly grateful to all of the people that I’ve worked with over the last nine years. When you work with hyper-talented people, and you work around super bright and interesting kids, you realize that the aspect of teaching that is really most rewarding is the fact that you’re working in service of a whole new generation of people. I’m super excited about where that generation is gonna go,” he said.

Other than the community, what will he miss most about Westridge? In typical Mr. Baldwin fashion, he opted for the humorous (but very true) answer: the breakfast burritos.