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.