Maya McFadden Photo
Hillhouse's Antoine Billy: Will be back in August.
Not quite three months into his new top job, Hillhouse High School Principal Antoine Billy has taken up a bet with some of his staff — that he will be returning to Hillhouse at the end of summer break, and that he won’t make the school find its sixth principal in less than three years.
If Billy wins that bet — which, he promised this reporter, he’s 100 percent sure he will — he plans to celebrate with a glazed Krispy Kreme donut in August. And a successful school year to follow.
Billy talked through that playful bet, his personal and professional background, and his goals for the school that he’s led since Feb. 20, during a recent interview with the Independent.
He has stepped into Hillhouse’s top role after a revolving door of permanent and interim principals in recent years: In March 2022, Glen Worthy stepped down as Hillhouse principal after six years in the job. Retired former Wilbur Cross Principal Peggy Moore filled in as interim until Mark Sweeting took over in July 2022. Moore then returned to serve another stint as interim Hillhouse principal in August 2023 after Sweeting resigned. The Board of Education hired Billy as the school’s latest permanent principal in January of this year.
Since he was 12 years old, Billy knew he wanted to become a principal of a school like the one he attended growing up in Harlem, to support the dreams of at-risk youth that he once resembled.
For the past three months, he’s been living out that dream as the principal of Hillhouse High School, one of the city school district’s two comprehensive high schools, which he reported has an estimated 1,146 enrolled students this year.
Billy previously worked as a math teacher at Wexler Grant School from 2010 to 2013 and then at Wilbur Cross High School from 2013 to 2017.
From 2017 to early 2024, he worked as an associate principal of New Britain High School, which he said has more than double the student population of Hillhouse. He said he knew he wanted to come back to New Haven at some point, and had long hoped to work at Hillhouse, where he spent one summer working as a math teacher during his time in the district.
Billy told this reporter that Hillhouse reminds him of his own high school while growing up in Harlem. He described it as a school with vibrant student personalities and talent that in recent years hasn’t provided its students with the opportunities they deserve.
When asked about the major challenges Hillhouse currently faces, Billy described everything from negative community perceptions of the second-largest school in the city to getting students engaged with their education to various personal obstacles and struggles in students’ and their families’ home lives.
A goal of his is to establish deeper relationships between the school and students’ families so that he and his team at Hillhouse can help connect them with necessary resources when non-academic barriers stand in the way of students succeeding in school.
Long term, he hopes to provide even more support out of Hillhouse’s school building itself — including more academic tutoring, access to drivers education classes, daycare for young parents, and help for students navigating the juvenile justice system. He also wants to offer mentorship programming to pair students with a consistent support team to offer wrap around services and help them from falling through the cracks.
“I want to remove every barrier that’s in the way of a kid’s success,” he said.
As these major barriers are addressed, Billy said, attendance, engagement, community investment, and assessment scores will improve. “They need the chance to just focus on academics,” he said. “Remove barriers and provide access and the rest will come.”
Billy seeks to inform his leadership decisions by collecting feedback and data, a favorite method for him as a math teacher. During his first days at Hillhouse, he said, district leaders suggested that Hillhouse shorten its homeroom periods at the start of the school day. Before agreeing, Billy asked hundreds of students on his first week on the job what they preferred during lunch waves. Out of the 600 students he asked, he reported, 597 said they would not want to shorten the homeroom period, and so Billy advocated to not make the suggested changes. “There’s power in student voice,” he said.
Billy's favorite poem, by Langston Hughes.
Billy also hopes to raise the school’s expectations of its own students through future policies. In regards to class attendance, Billy said he no longer wants to allow for students to miss class and be able request a make-up packet of work from their teacher. Instead, he wants parents and the school to hold students to a higher standard of understanding “you don’t get paid if don’t show up to work,” he said.
He tells his students wisdom he’s learned from first-hand experience, like “getting here late gives you bad habits for life” and “dress yourself accordingly.”
Billy added that he recognizes that these goals will require him to continue building trust with the students and staff.
“There’s trauma for everyone due to that instability,” he said in reference to just how many principals the school has had of late. “But I tell them all everyday, ‘I’ll be here in August.’ ”
Upon his arrival Billy aimed to acknowledge the distrust felt by both students and staff caused by the departure of past leaders. To gain his community’s trust, he plans to be consistent, accountable, firm, and warm, he said.
Hillhouse’s years of inconsistent leadership has led for students and staff to work in survival mode, Billy said. He’s ready to change that. “The talent and resources are in the building. It’s about the management of that talent and resources. That’s a challenge that I’m up for,” he said.
As a leader Billy has also been focused on learning before making large changes to the school. So far he’s learned that Hillhouse is a place that has a strong sense of pride for students and staff. “I want to build up that legacy of pride and remind people it’s a badge of honor,” he said.
From its athletes and musicians to educators and academics, Billy said his mission is to remind all that “Hillhouse is a powerhouse.”
And with that comes the task of reminding students of “what shoulders they stand on” so they can respect their school, Billy said.
One way Billy has worked to provide that reminder to students that their school cares for them is by kickstarting school days with music as students enter the building every morning.
Rain or shine, Billy welcomes his students to school in the morning to encourage students and to show parents dropping their students off that getting them to a school that cares about them pays off.
Like his favorite poem “Harlem” by Langston Hughes, Billy reminds students, staff, and parents that “our circumstances shouldn’t hold us back from our dreams” because they didn’t hold him back.
Billy has known he wanted to be an educator since second grade. He recalled his second grade teacher Ms. Young inspiring him as “she always took care of me” despite his frequent misbehavior in the classroom.
As the oldest of three boys raised by a single mother, Billy said, similar to his students at Hillhouse, he dealt with food insecurity and a lack of resources. However, he recalled, after a day of misbehaving in his second grade class with his teacher Ms. Young, she didn’t give up on him and stayed after school with him after he missed the bus and waited for his mother to pick him up.
While waiting with him, his teacher brought him to “the nice store” known as Blimpie, which his family couldn’t afford, to get a sandwich after school. “From there I knew I wanted to be a teacher and treat my students with that same respect,” he said.
Due to the lack of resources at his high school, Billy had to teach himself how to use a TI84 calculator and a computer because his school didn’t have either and had low expectations for the students.
"Take This School To The Top"
Not only does Billy plan to work on student needs but also staff needs. He plans to keep his staff up to date with frequent real time data reports on school goals. He recognizes that the more his staff feel supported, the more support will trickle down to the students, he said.
Billy described his past three months on the job as a listening and learning tour.
He’s balancing gathering input from students and staff with making gradual changes to show the action behind his words.
He spent his first month learning that one reason students were late to their first period was because the school’s bell system would ring at 7:30 a.m. but not again until 8 a.m. when students are expected to rotate to their first period.
Correction: a previous version of this article incorrectly stated that Billy implemented a new daily bell for students homeroom class rather than a 7:40 a.m bell to inform students when were late to their 1st period class.
So, while he would see students arrive to school on time at 7:15 or 7:30 a.m., they would roam the halls and not report directly to their classrooms until the next bell rang a half hour later. So Billy has since added another bell between 7:30 and 8 a.m. to remind students to report to their homerooms.
Additionally during the first months on the job, staff and students informed him of the school’s lack of working bathrooms. Billy sprung into action by collecting data on the impacts of only having access to one of the school’s total 12 bathrooms. The data on bathroom usage showed it was a major cause of flooded hallways throughout the day and students missing class. Once he shared the data with the district, Billy said repairs came within two weeks.
Billy concluded that Hillhouse’s dreams will no longer be deferred under his watch. He invited the community to help him in his mission to restore the school’s legacy and support its students. “We’re going to take this school to the top,” he said.