Jerome Winegar: The rise and fall of South Boston High School

Jerome C. Winegar sat at his desk in St. Paul, Minnesota when his phone rang. He was weeks away from taking over as headmaster of South Boston High School.

It was Federal Judge W. Arthur Garrity, and he had specific instructions for Winegar.

“Mr. Winegar, I don’t care, whatever you say you need. I’m going to order it,” Garrity told him. “Just get my face off the front of the Boston Globe.”

In December 1975, the South Boston High School was placed under court receivership, making it the only school in the country under federal control. Keeping the school open became a symbolic test of the wisdom of the Phase 2 busing system and the soundness of Garrity’s judgement. Many activists in South Boston and Roxbury were determined to humiliate Winegar, and not even Garrity thought South Boston High had a chance.

On December 17, 1974, the court ordered contingency plans to close South Boston High and disperse its students. Garrity originally told Winegar to stabilize the school so that the plan could go forward. However, Winegar convinced the judge to let him try to keep the school open.

On Winegar’s first school day, April 26, 1976, the new headmaster stood on the front steps, gazing through his tinted gold-framed glasses at a crowd of about 180 white students who had gathered in protest. Despite warnings from his personal bodyguard, he wanted to talk to them.

“I told them who I was, and that I was going to be the new headmaster of the school,” Winegar said. “I said it’s important that we get the day going, and that we get the year going, because we are in fact going to straighten this out, one way or the other.”

Out of about 800 enrolled students, around 80 white students and 50 black students attended school that day. They were outnumbered by hundreds of protesters, journalists and state police officers that surrounded Monument Hill. Inside, metal detectors searched for weapons and contraband. At 10:30 a.m. the school was evacuated because of a bomb threat.

In January 1976, Winegar was recommended by a committee of parents whose children attended schools in South Boston to take over their high school. A month earlier, Judge Garrity removed the school administration after he found that South High had violated his desegregation orders. Due to the federal receivership, Winegar was the only headmaster who had not been directly hired by the School Committee. Even though he had the support of many parents, Winegar said he was not invited to the headmaster’s committee meetings until a court ordered it.

Winegar said many of the protesters outside his school worked for the central administration of the school system. South Boston parent and Boston Public Schools Purchasing Head Buyer Jane DuWors confronted Winegar on the day they first met.

“Whenever you’re leaving, let me know and I’ll buy you your first tank of gas out of town,” Winegar said DuWors told him. “And I said, be careful, because I’ll hold you to that when the time comes.”

DuWors refused invitations to comment.

Commencement in 1976 marked the end of the first year of Phase 2 busing and two difficult months for Winegar. The commencement speaker was School Committee member Elvira “Pixie” Palladino. When she finished, Winegar said Palladino told the students to throw their mortarboard caps at their new headmaster. While not every student did, Winegar said he was forced to duck as the caps flew his way.

The Phase 2 plan, implemented in the second school year after the Morgan v. Hennigan ruling, expanded mandatory busing citywide. Before desegregation, one third of pupils took the bus to school. In Phase 2 desegregation, every neighborhood in Boston was affected except East Boston and about half of the city’s public school students were bused to racially balance 162 schools in nine school assignment districts.

During the school year before Winegar arrived, South Boston High School had descended into chaos. The school suspended 1,600 students in the 1974–1975 academic year, a record for the city. Discipline was such a major problem when Winegar took over that for two months, he met until 10 p.m. every night with parents to get their teens reinstated.

During the summer of 1976, South Boston High School spruced up its campus to encourage students to attend. Classrooms were repainted. New equipment was ordered for the gym. And a group of faculty and parents walked door-to-door to convince parents to send their teenagers.

On the first day of school, September 8, 1976, only freshman were called to attend. One out of four showed up. As students returned to school later in the month, fights broke out. After a brief crackdown during the week of October 4, 1976, the school calmed down and students stopped roaming the hallways. South Boston High School later created a “school within a school” where suspended students sat in a room together instead of being sent home. Winegar said that students who fought sat next to each other so that they would have a chance to get to know each other.

“I said, you know, ‘the first day they won’t be happy,’” Winegar said of the students sitting next to one another. “The second day they’ll start talking about cars, the third day they’ll start talking about girls and then, guess what, they’ll enjoy each other. And I know one thing’s for sure. Those two will never fight with each other again.”

In April 1977, South Boston High School filed a proposal with Judge Garrity to start alternative programs, including the hiring of its first music teacher, creating a community-based reading program and expanding off-site programs at Boston City Hospital and the Albany Street Garage.

As part of Phase 2 busing, 18 schools were paired with 23 businesses and universities. Southie High worked with the Federal Reserve Bank of Boston, which provided mini-classes to inspire students to go to college, receive training in stenography and prepare students for work study jobs. Every student at the school was able to visit the bank, and retirees worked as tutors at the school.

After a calm winter and spring, Winegar’s first full school year ended in violence. On May 11, 1977, a group of black students gave their headmaster a list of demands that included moving the school to a neutral area, hiring more black teachers and guaranteeing their safety. The students led a walkout that emptied out the school. Ten percent of the 120 member teaching and administrative staff at South Boston High School was black.

Later that week, about 50 students were suspended from school for fighting, and black leaders accused Winegar of racism.

Dealing with a racially charged climate wasn’t unusual for Winegar. He grew up in segregated Kansas City, Missouri during a time when lynchings still occurred in the South. However, he learned at an early age to treat everyone with respect.

“I really became aware of everything that was going on from my uncle, who ran a gas station,” Winegar said. “He said, ‘Jerry, these people are no different from us.’ He said, ‘if they’ve got their money, they’ve got their dollar, I sell them their gas.’”

In 1959, Winegar was hired as an English teacher at East High School in Kansas City, Missouri. Winegar spent the next nine years there, but said it was clear he saw the world differently than the school administration. He disagreed with many of the school’s policies, including the dress code that said black girls were required to wear their hair straight, and black boys couldn’t grow facial hair.

Winegar was 38 years old and an assistant principal at Wilson Junior High School in St. Paul, Minnesota when he was asked to take a pay cut and become headmaster of South Boston High School.

As the principal of a school under federal receivership, Winegar was given more independence than other administrators. The hiring and transferring of teachers to janitors were typically controlled by an elected school committee. Personnel issues were politicized, and Winegar said he spent months trying to remove four no-show hires off his payroll.

The faculty and support staff of South Boston High School were hand picked by Winegar and three lieutenants he brought from Minnesota. Development programs were created to allow help staff and parents to take classes at South Boston High School that could be used to earn a degree at UMass.

Judge Garrity lifted receivership of Southie High on August 30, 1978 but maintained supervision over the school system. The state police ended daily patrols of the high school the previous school year. No student would be suspended in the coming school year, and the metal detectors would be removed the next summer.

Southie High also turned around its academics. The year that Winegar came to Boston, Southie scored 18th out of 19 public high schools in reading and only 22 students of its senior class were college-bound. Four years later, South Boston High School was fifth in the city in reading and more students went to college than any year in the school’s history. Fifteen Southie High students were inducted into the National Honor Society in 1979.

Off campus, rivals watched as South Boston High School supplemented its budget with grants, built partnerships with organizations like the Family Service Association that provided two social workers and started a student-staffed meal program for elderly South Boston residents. In 1981, the Boston Globe Spotlight Team found that Southie High had one counselor for every 150 students, a ratio lower than the region’s suburban schools. Boston public high schools typically had one counselor for every 400 students.

Years after the end of federal receivership, Judge Garrity continued to protect South Boston High by rejecting attempts to take away Winegar’s independence. In a brazen act of irreverence, Winegar called out Mayor Kevin White and other politicians for being silent about an attack on school buses in 1979. Winegar said he regrets the public exchange where he was quoted by the Boston Globe as saying: “He’s done nothing to help us since I’ve been here, and you can print that in capital letters.”

In 1987, the federal appeals court released Boston Public Schools from court supervision. South Boston High School was on its own, and Winegar said that the School Committee sought to sabotage his school.

In 1989, the School Committee pushed South Boston High School to its enrollment capacity of 1,200 students and then added 230 more Cape Verdean students from a closed school. The bilingual education program’s student-teacher ratio rose to twice the legal limit.

Outside school, the city was struggling with a crime wave caused by drug gangs. The School Committee responded by cutting South Boston High’s plainclothes security force in half.

The South Boston Information Center, an organization that fought Winegar since 1976, accused the headmaster of losing control of his school. After 13 years as headmaster, Winegar was removed and given a post in the central administration. After 20 years of service, Boston Public Schools fired him. Winegar knocked on Jane DuWors’s office door to collect the money for his first tank of gas out of town.

“‘Mr. Winegar, I know you may think that I’m happy about this, [but] I’m not happy about this at all,’” Winegar said Duwors told him. “‘People in South Boston understand what it means to make a commitment for 20 years—we’ll never forget that.’”

*Correction: An earlier version of this story incorrectly stated that black girls attending East High School in Kansas City, Missouri in 1959 were required to wear their hair curly. The dress code required them to wear their hair straight.