Why Is a High School in One of America's Richest Counties Still Failing?
For 50 years, Bassick High School in Bridgeport, Connecticut has been neglected and underfunded—despite being just a few miles from extreme wealth.

BRIDGEPORT, Conn.—The inequalities that afflict Connecticut’s largest city have been evident since 1961, when the veteran journalist Nancy Hendrick wrote a blistering column in the Bridgeport Sunday Herald.
“[F]or quite a few years now not enough people in Washington have cared what's happening here—and in a hundred other Bridgeports across the country,” she wrote. “What frustrates us is that in this crowded, unplanned, unlovely city, there is so much to be done that no one can tell where to start.”
Later that week, The Connecticut Post reported that when state educators came to Bridgeport to evaluate Bassick High School, they praised the teachers but balked at the city’s lack of financial support—noting that students were forced to pay for their own books, science equipment, globes, and maps.
“This situation makes a mockery of a free public education,” they wrote. “If Bridgeport were a poor community in a poor state in a poor nation, this condition might be more easily understood.”
Fifty-five years later, Bridgeport is now largely a poor community—despite its location in the richest county in one of the nation’s richest states. The city has sprawling green spaces and gracious parks, some designed by the famed Central Park creator Frederick Law Olmsted. But is perhaps better known for its long line of corrupt politicians, including the current Mayor Joe Ganim, re-elected last year after spending five years in prison for embezzling taxpayer dollars.
Poverty and violence persist. Bridgeport is commonly labeled one of the most dangerous cities in the U.S. Twenty percent of the racially diverse population—which numbers close to 150,000—are living in poverty, including a quarter of all the city’s youth. But just 12 miles away in Westport, where Martha Stewart and Paul Newman once lived beyond the Maserati dealership, the poverty rate is only 2.6 percent.
“Fairfield County is one of the richest counties in America but you wouldn’t know it by looking at Bridgeport,” said Eric Lehman, an English professor who teaches Connecticut history at The University of Bridgeport, and the author of the book Bridgeport: Tales from The Park City. “There’s a huge disconnect.”
Nowhere is that economic divide more apparent today than in the schools. Bassick High School has continued to struggle since receiving that damning state evaluation in 1961. Only 15 percent of Bassick students tested proficient in language arts on last year’s new Common Core-aligned state tests. None were proficient in math. Nearly half of all Bassick teenagers missed 18 days of the 2014-15 school year, compared to 10 percent of students in the state overall. Despite Connecticut’s high-school graduation rate of 85 percent—above national average—Bassick trailed at 62 percent in 2015.
Bassick first opened as a middle school in the ‘20s to meet the demands of a city teeming with European immigrants seeking jobs in factories that produced everything from sewing machines and corsets to guns. The school’s entrance hints at Bridgeport’s past grandeur, with tall white columns ascending above a steep staircase—but has long fallen into disrepair. In a meeting earlier this year, the school board approved $1.5 million to finally fix a leaking roof.
While the educational woes of big cities like Chicago, Detroit, New York, and Los Angeles dominate national headlines, persistent failure in schools like Bassick is no less challenging or urgent.
“In the city of Bridgeport, we have 18 schools that are failing. Of those, 13 have been failing for over 10 years,” said Kenneth Moales Jr., a pastor and former school-board member. “Bridgeport is a microcosm of low-performing school districts [all over] the country.”
The divide between the wealthy and successful suburbs just outside of Bridgeport and a failing school like Bassick results in large part from state-funding discrepancies. In 2005, a coalition of education groups filed a lawsuit complaining that Connecticut was failing to fund schools adequately or equitably. Evidence continues to mount in the plaintiffs’ favor—and after more than a decade in the state court system, it is now being argued before Connecticut’s Superior Court.
A newly released report from the U.S. Department of Education found that in 2015, Connecticut spent 8.7 percent less per student in its poorest school districts than it did in its most affluent. In Bridgeport, that comes out to $13,883 per student compared to the state’s $15,700 per-student average and ultra-wealthy Greenwich’s $20,747 per-pupil, according to the Connecticut School Finance Project.
This difference leads to sharp inequality in a student’s school experience. Bassick had four guidance counselors for its 1,200 students in the 2012-13 school year, for instance, while Greenwich’s 2,700 students were served by 18 guidance counselors, according to the lawsuit. A recent New York Times analysis of wealth and school-achievement data found that Bridgeport sixth-graders were lagging nearly two grade levels behind while their Greenwich peers were typically two grade levels ahead.
The starting salary for a teacher with a master’s degree in Bridgeport is $44,101; five miles away in Trumbull, it’s $57,516, according an analysis by Bridgeport Public Schools.
In the 2007-08 school year, Bassick reported 881 disciplinary offenses. One parent, Evelyn Medina, often feared for her children’s safety, she said, frequently receiving messages that the police had locked down the school because of another serious fight. Medina’s children knew to walk away from violent incidents but struggled to keep up in their classes. Her daughter was slated to graduate in 2010 but dropped out in her senior year.
Her son, with dreams of becoming a mechanic, persisted through tough classes. Three years ago, Medina and her daughter watched with pride as he got his diploma. Still, the moment was bittersweet for her daughter, who by that time had a child and a job but no degree.
“The only thing she said was ‘He made it and not me,’” Medina said. “She started crying. ‘Why didn’t I finish?’”

Other local parents have been unable to wait around for Bassick to improve. After her older daughter started to struggle academically and behaviorally at Bassick, Dione Dwyer began working three jobs—sometimes clocking seven days a week—so she could send her younger daughter to Bridgeport International Academy, a small private school. Her teenager takes two city buses, starting at 6:50 a.m., to get to school on time—a sacrifice the family happily makes for the education she is receiving there.
High-school turnaround is generally seen as one of the hardest tasks in urban education. One of the few places to experience success was New York City, which improved the education of students slated to attend the lowest-performing schools by closing them and opening new, smaller high schools.
Far smaller in scope and with nowhere near the resources of New York City, Bridgeport set out to remake Bassick High School in 2010 when it received one of Obama’s $2.1 million School Improvement Grants.
The then-Superintendent John Ramos took a reform approach that stipulated replacing the principal but keeping the rest of the staff, with a heavy emphasis on professional development, curriculum improvement, and expanded learning time. And when the former Connecticut Education Commissioner toured Bassick with reporters a year after it received the federal grant, he declared that the chronically underperforming high school had entered a “new era.”
Yet in 2012, the Connecticut Department of Education labeled Bassick a Turnaround School, a designation under federal education law for the worst-performing schools in the state. In 2013, Bassick’s basement-level test scores prompted the reform-oriented advocacy organization ConnCan to give the school an F rating in every single academic category. This year, the school was designated a Category 5 Turnaround School because it has failed to shake that distinction for three years.
Graduation rates have declined and then risen again. Scores on the SAT remain low and students continue to lag behind their peers on the state standardized test. Of those who graduated from Bassick in 2014, only about a third enrolled in college the following fall but 80 percent of them—a bright spot—returned for their second year, according to state statistics. (Read more about the forces guiding Bassick High from The 74.)
Fran Rabinowitz, the well-regarded interim schools superintendent who earlier in her career spent 29 years in the Bridgeport schools, said that when she first evaluated Bassick in 2014, the main challenges were the deplorable condition of its 85-year-old building, and the wide variation of talent among the teaching staff.
The school has now been through multiple superintendents, and three principals just in the past three years—some with minor successes here and there—but none have been able to turn Bassick around for good. Just this month, four area university presidents joined in a letter to the current state commissioner asking her to intervene, saying the dysfunction of the Bridgeport school board “called into serious question the board’s ability to carry out its charge.”
A host of programs have been put in place under Rabinowitz to try and keep Bassick students interested and on track to graduate and to address their learning deficits. Reading and math intervention programs are given to the ninth-graders; some classes at all grade levels begin with cognitive-conditioning exercises to help below-grade-level students hone their critical-thinking skills.
Special attention is focused on freshman attendance and credit retention. If students are in danger of failing or not earning enough credits, they meet with school staff to sign a contract detailing how they will right their course. If they arrive late, they must stop at the principal’s office to get a pass before they can go to class. The freshman monthly attendance rate now regularly surpasses 90 percent. “If you don’t catch them [as 9th-graders], you lose them,” said Kathy Silver, a much-loved former art teacher who is now the freshman-academy assistant principal.
Bassick also introduced career pathways in business and science and technology, a program made up of theme-based electives across grade levels. There are six Advanced Placement classes and other opportunities for students to seek college-level work at local community colleges.
Rose Charles, 19, and Jada Pickett, 18, both seniors, have their lives after Bassick planned out. Charles, who plans on attending Clark University in Worcester, Massachusetts, next year, said Bassick is “what you make of it.” She and Pickett said the school has gotten a lot safer compared to their freshman and sophomore years when fights were common. Student arrests district-wide have gone down dramatically from more than 280 a year to 40. Both girls are a little jealous of the younger students who will have more access to class computers and smart boards.
Uncertainty about Bassick’s future remains. Connecticut Governor Malloy has proposed a budget that cuts state funding to CommPACT, a three-way partnership between Bassick, the teachers unions, and the University of Connecticut, leaving administrators to come up with a new source of money for parent-engagement programming. Meanwhile, some members of the fractious Bridgeport school board are openly hostile to Rabinowitz at the same time they are trying to attract her permanent replacement. No superintendent “worth their salt” will want to come Bridgeport, one board member observed.
Moales, the pastor and former board member, is disappointed by what he said is Bassick’s and other Bridgeport schools’ too-slow progress. He thinks drastic actions would need to be taken to get the results students deserve. “It’s frightening,” Moales said. “Bridgeport is going to struggle for another seven to 10 years easily.”
But Ferris, the parent leader, is more cheerful about Bassick’s future. Back in October 2013, a visiting committee of educators from the New England Association of Schools and Colleges spent four days with Bassick teachers, administrators, and students, and wrote in their 80-page report that the school conveyed a “sense of family and belonging,” and the teachers had positive attitudes. “It is clear that Bassick students are connected to the school and especially to the adults in the school,” they wrote.
“It’s not just money. We need the leadership. We need to build more community relationships. We need to build our parent component,” said Ferris. “I just think it has the potential to be a great school.”
For Dwyer, the mom who worked three jobs to send her younger daughter to private school, those efforts might not come soon enough. She said she knows Bassick has been making improvements but she is not sure if it will be ready to give her 11-year-old son the education she so wants him to have.
“I try not to think about that,” she said.
This story was produced in collaboration with The74Million.org.