When Gary Highsmith walked into the admissions office at Southern Connecticut State University, he had no idea where the future would take him. Now, as the new first Black superintendent of Hamden Public Schools, he reflects on the journey that got him there.
Highsmith grew up in New Haven with five siblings and lived in a single-parent household. He found himself having to heavily rely on family and the community when his mother died unexpectedly when he was 13-years-old.
“The relationships with my sisters, in particular, became more important,” Highsmith said. “Relationships with my friends, relationships with people who worked at the Boys Club, now the Boys and Girls Club. The people who worked there and my teachers became critically important in my personal life.”
Highsmith said he was always unsure of attending college but knew he loved American history and spent a lot of time at the library. He decided to take a chance on himself and enroll in SCSU after driving past the school on his way to visit a friend.
“I drove by Southern and said ‘I’m not quite sure what I’m going to do with myself, here’s a college over here in New Haven,’ so I just got off the bus and went over to the admissions office and asked, ‘What do I need to do in order to come here?’,” Highsmith said.
Highsmith earned a bachelor’s degree and master’s degree in American history, with a social science concentration, a teaching certificate and a sixth-year degree in educational leadership — all from SCSU.
When reflecting on role models throughout his life, Highsmith noted several teachers, athletic coaches and Boys & Girls Club staff members who contributed to his personal success — including former East Rock Community Magnet School principal and teacher Sal Punzo along with Tom Anastasio. Anastasio was a teacher and basketball coach in New Haven who helped Highsmith acquire a summer job at Yale New Haven Hospital which propelled his professional career and allowed him to pay for college.
Highsmith eventually decided to pursue a career in education after meeting John Dow Jr., New Haven’s first Black superintendent.
“Meeting him and talking to him and learning from him about education inspired me to go into it so I started working in New Haven in 1994,” Highsmith said.
Highsmith worked in different New Haven schools, including Augusta Lewis Troup School, Roberto Clemente Leadership Academy and James Hillhouse High School. Over his time, he taught classes like African American history, social problem solving, language arts and social studies.
He then became the assistant principal at East Rock Community Magnet School before becoming the principal of Beecher Elementary School, both in New Haven.
While at Beecher, Highsmith received a call from former Hamden Public Schools superintendent Alida Begina asking to discuss administrative vacancies within the district. Highsmith then applied to be the principal of Hamden High School, despite having no prior experience working in high schools.
“I went to high school,” Highsmith said. “I didn’t work in a high school at all … so it was obviously a very steep learning curve.”
During his time as principal, Highsmith said one of his proudest accomplishments was implementing a program for freshmen commonly referred to as “freshman academy,” in hopes to increase the percentage of students who passed and moved on to sophomore year. This program dedicated school counselors, teachers, an administrator and a social worker to work only with freshmen.
Research showed that if a student repeated their freshman year or didn’t have enough credits their second year to become sophomores, they were at much higher risk of dropping out.
“We were able to increase that percentage of freshmen who became sophomores from 84% to 98-99% of students,” Highsmith said. “Our dropout rate and graduation rate reflected that, it just got so much better so I was very happy to see that happen.”
Highsmith went on to say that his greatest accomplishment has been the bonds he has formed with students throughout his career.
“The thing I’m proudest of is my relationship with students because that’s endured over time,” Highsmith said. “Students who I was their principal in elementary school, whether I was their teacher, whether I was their high school principal, or assistant principal, I still have a relationship with those students. We see each other, we talk to each other, we call each other and it’s important for me to maintain those relationships over time.”
Being a positive role model to the kids he meets and leads means a lot to Highsmith, he said.
“It means a lot because when I decided I wanted to teach it really was because I understood how important a quality education is,” Highsmith said. “I understood how important it was for kids to get that education from somebody who really cared about them a lot more than whether they were just learning to read and write. Somebody who students could see that had a similar situation to them as they were growing up and I wanted to make sure I did it in a community that I lived in.”
Highsmith also recognizes the importance that comes with being the first Black superintendent within Hamden.
“It means a lot to me to be in this position because at the high school, at Hamden High, I was the first Black principal they’ve ever had in the district and the first Black permanent superintendent,” Highsmith said. “I understand the responsibility I have and what representation means at whatever level, so I embrace that, I embrace the responsibility that comes with it.”
Highsmith explained that as more underrepresented races and ethnicities hold positions of power, children will grow up viewing it as normal.
“One of the things that is important is representation because you hear ‘well you can be anything,’ but then if you don’t see it, it just becomes talk,” Highsmith said. “When I’m in the middle school or the high school or even the elementary school, in particular, there have been African American boys who ask me what I do. Then I tell them, and they say ‘wait, so you’re in charge of everybody?’ and the one thing you do realize is that there may be African American boys who don’t see black men in positions of authority,” he said.
Highsmith said he wants to make sure that students are getting what they need for a quality education.
“No matter who they are, no matter what language they speak, no matter how they identify in terms of sexual orientation and sexual identity, I want to be sure to give them whatever they need to be successful,” Highsmith said. “To be able to ensure that students have the human and material support that they need to be successful is critical.”.
He went on to explain that he wants to advocate for a budget that allows the district to provide for students as well as make sure all of the schools remain connected as a system of schools.
Highsmith said the idea of making sure that the schools within the district are “racially balanced” is important.
“If the neighborhoods are segregated, then the schools will be segregated.” Highsmith said. “So while we can’t tell people where to live, we can begin to put together a process that would make our schools better racially balanced.
Highsmith has also received support from the Hamden Board of Education.
Melissa Kaplan, chair of the board of education, praised the selection of Highsmith in a press release announcing Highsmith’s appointment on June 27, 2022.
“We are inspired by the fresh ideas that Gary will bring to Hamden’s major challenges,” Kaplan said. “The Board is thrilled to have found a transformational leader who also understands Hamden’s needs.”
To Highsmith, the future of Hamden Public Schools is bright and he is looking forward to not only seeing what can be accomplished but also to serving as a positive example for the community.
“I look forward to hopefully trying to inspire other students or other young people or other teachers or other principals to become superintendent if that’s what they want to do,” Highsmith said. “I want to make sure that students have equitable outcomes all the time.”