The superintendent’s announcement in April was shocking: six schools in Bridgeport, Connecticut, would close in June. Just a few months’ notice for a decision that would upend an entire community. Parents were angry, children were broken-hearted, but Leslie Caraballo and her fellow advocates were determined to find an answer. They read the bylaws, and what they discovered changed everything: “We realized that it wasn’t that easy, that we had rights.” The district was required to conduct a comprehensive school closure study with parent involvement鈥攁 year-long process, not a months-long decree. Armed with this knowledge, she educated other parents about their rights, and the superintendent had to publicly retract her decision on TV news, apologizing and announcing the schools would not immediately close. The victory was temporary鈥攖he district still planned closures, but now they had to follow the proper process and listen to parents. For Leslie, this moment crystallized a hard truth: “We cannot beat the government when it comes to the educational system, so I need to devise a plan that’s going to become the solution.”
Meet Leslie
Leslie Caraballo is a Bridgeport, Connecticut parent advocate who was endorsed by the mayor for school board and has become a go-to resource for parents throughout Connecticut navigating educational challenges. Through social media and word-of-mouth, she helps parents understand their rights, especially regarding IEPs and special education services. Her advocacy work grew from helping individual families to taking on district-wide policy fights, ultimately leading her to envision a much bigger dream: a low-cost private school that would serve Bridgeport children with wraparound family services, joyful staff, and a philosophy of lifting families up rather than bringing them down.
The Journey
Leslie’s transformation as an advocate happened organically through a simple backpack drive in her community. Parents soon began reaching out with questions, initially through Facebook Messenger, and word spread quickly. “It got to the point where other people from other cities in Connecticut were reaching out to me for help,” she recalls. She found herself explaining educational rights, IEP processes, and special education entitlements to parents who had been denied services their children deserved.
Her biggest frustration came from working within existing political structures. “I was hitting a brick wall when I kept standing with politicians because it all circled back to politics. It all circled back to what they wanted, not what the parents wanted.” The pattern was maddeningly consistent: parents would request basic needs like tutoring hours for IEP plans or better security after people walked into schools without proper identification. Administrators would promise help, months would pass, incidents would repeat, and parents would again hear the same empty assurances.
The breaking point came when the district announced a $129 million award to build a new high school while simultaneously cutting critical special education positions and “mingling the special education kids with the regular population.” Parents kept asking: if you have millions for new construction, why can’t you fund basic security and services? “It was so frustrating, because it seemed like they weren’t listening,” Leslie says. She found herself delivering the same disappointing updates to parents repeatedly, watching them become frustrated and lose hope.
Looking back, Leslie wishes she could tell her younger self: “It’s okay, just breathe, and also do some research. Don’t rely so much on the people in charge and believe everything they say. Don’t assume you hear one answer to a question, and that’s the truth.”
Making a Difference
Leslie’s approach to empowering parents combines education with direct connection to trusted resources. In one pivotal conversation, she helped a parent who couldn’t get proper help for her son by arranging a Zoom call with a special education teacher she trusted. The parent could ask questions directly and get honest answers. “After the parent saw this, they were shocked. They had no idea that they were entitled to that, and they didn’t even know that the school had to follow their son鈥檚 education plan.”
This experience highlighted a common problem: parents don’t know what they don’t know, and school districts aren’t always forthcoming about available services and rights. Leslie bridges that gap by connecting parents with knowledgeable sources and teaching them to question in order to get official answers.
The Ultimate Solution
Frustrated with systemic failures, Leslie now dreams of founding her own low-cost private school for Bridgeport children. Her vision goes far beyond academics: staff and bus drivers dancing outside to welcome children with music, telling them “we’re so happy that you’re here” at arrival and “we’re so sad that you’re leaving, but we’re happy that you’re going to be here tomorrow” at dismissal.
The school would include a parent center to help families facing eviction, a clothing pantry for children who come in with the same clothes repeatedly, hygiene products, and food services. She’s already in talks with teachers, ready to leave the public system if her plan comes to fruition.
Words of Wisdom
“Don’t rely so much on the people in charge and believe everything they say. Don’t assume you hear one answer to a question, and that’s the truth.” Leslie’s advice reflects hard-won wisdom about questioning authority and doing independent research. Her journey from individual advocacy to potential school founder shows that when systems consistently fail children and families, sometimes the solution is creating something entirely new.
Get Involved
Leslie continues advocating for Bridgeport families while exploring plans for her private school that would serve not just students but entire families facing economic and educational challenges.
