Raymond Flynn: The South Boston insider who struggled to keep his alma mater open and ascended to political prominence

During four days of violence in October 1979, bands of boycotting high school students roamed the streets of Downtown Crossing, attacking and intimidating black workers and students. One of the groups had just chased away some black youths near the Common. Two black teens, Allen Moore, 19, and Denise Smith, 16, were having lunch nearby when they saw the angry group approach. Moore told his friend to run as he pulled out a pair of scissors from the upholstery shop where he worked.

City Councilman Ray Flynn saw the imminent attack as he walked out of the State House. He ran down the hill and was met by State Sen. Joseph F. Timilty in time to break up the fight.

“I don’t remember much about that day,” Flynn told People Magazine in 1984. “I’m told I said ‘If you want to get to them, you’ll have to go through me first,’ but I just don’t remember.”

In that fleeting moment, Flynn, a Southie icon of the anti-busing movement, would get a second look as a leader who could bridge communities. Though the future mayor’s position against busing never changed, Flynn was able to transcend South Boston’s violent, racist image. But, his neighborhood wasn’t given the same opportunity during the years Boston struggled with school integration.

Throughout the 1960s and early 1970s, Southie’s leadership vigorously fought school desegregation. As School Committee chair, South Boston politician Louise Day Hicks refused to admit that black schools in Roxbury were disadvantaged even though the school system spent 20 percent less per pupil in the neighborhood than in other communities and Roxbury’s seventh graders were 25 months behind the national average in reading.

Hick’s School Committee refused to comply with the state’s Racial Imbalance Law placing more than $200 million in state funding for new schools in jeopardy. After new magnet schools were built in 1971, the School Committee refused to hire specialized teachers so the schools could serve their purpose. School Superintendent William J. Leary pleaded to find the money to staff his schools by eliminating $4 million in patronage jobs directly controlled by the school committee. In schools like South Boston High, tool counters made $20 a day and truant officers took home the same pay as a police lieutenant.

Boston’s working class neighborhoods already felt under threat when busing was ordered in 1974. Urban historian Sam Bass Warner’s book “The Way We Really Live” shows how Boston lost 12 percent of its population to the suburbs between 1920–1970. Wealthier Bostonians had hollowed out the city’s tax base and 228,000 workers commuted into Boston daily.

With the city nearly bankrupt, Mayor John Hynes tried to redevelop working class neighborhoods to attract wealthier residents. After being blocked by protesters in the North End, the Boston Redevelopment Authority flattened the West End between 1958–1960. Sociologist Herbert Gans wrote in “Urban Villagers” that destruction of the neighborhood was so fast that residents didn’t have a chance to organize and articulate their grievances.

Theodore Landsmark, a former Flynn aide, said the redevelopment of the West End made ethnic enclaves like South Boston even more resistant to outsiders.

“When that neighborhood in particular was torn down, it made all of the more isolated communities feel they really had to hold on to their values, lest they become like the West End,” Landsmark said.

Starting in 1974, scenes of violent protests in  South Boston and Charlestown were common occurrences on the network nightly news. On the first day of school, 18 buses returned to the yard damaged. For the rest of the year, as many as 194 police officers patrolled inside and outside South Boston High School and another 100 officers secured the bus routes to the school. Law enforcement alone cost the city $2 million in the first 18 days of busing.

On Dec. 11, 1974, Southie parents barricaded South Boston High School after a 17-year-old white student, Michael Faith, was stabbed. Police had to rescue black students bused from Roxbury out of the back doors.

Faith wasn’t the intended target of the stabbing. He was walking down the hallway when he saw everyone was stopped. A black student reached for his back pocket. Faith hit him with his backpack, which contained the towel he had used for swim practice. Faith suffered a puncture wound to his liver and lung.

“I didn’t see the knife there at all at that time, but I knew something was wrong,” Faith said. “I wish I had books [in my bag]. I would have knocked the sucker out.”

Five years later, Faith ran into the man who stabbed him on Boston Common. He forgave him for what happened and said it felt like 10,000 pounds had been lifted off his shoulders.

“I had never experienced anything like that before,” Faith said.

Parents began organizing anti-busing groups like the South Boston Marshals, Restore our Alienated Rights (ROAR) and the South Boston Information Center. They relied on elected officials like Flynn to march with them and speak at their rallies.

“He [Flynn] was at all the meetings,” Fran Johnnene, a member of ROAR who hosted meetings at her house in Hyde Park. “He was a supporter of the parents. He wanted to help them.”

In March 1974, Flynn petitioned for a city-wide referendum on forced busing. If allowed and passed, a referendum against busing would have given elected officials a political shield against the Department of Education’s effort to desegregate Boston schools.

On June 24, 1974, U.S. District Court Judge Wendell Arthur Garrity ordered busing to immediately desegregate Boston schools. School districts across the country had already been desegregating for almost 20 years before Boston faced its court order. By 1964, a series of Boston Globe’s editorials showed a clear pattern. Communities whose leaders fought desegregation orders could expect disruptive classrooms, while municipalities like Springfield who accepted the transition were able to peacefully prepare their electorate.

In South Boston, politicians fought in the streets, on Beacon Hill and Capitol Hill. They pressured their congressmen, lobbied the White House and filed appeals in court.

Flynn said that he sat in the John W. McCormack Post Office and Courthouse to read the case documents of Morgan v. Hennigan and listened to Judge Garrity’s ruling. He said he realized that the city was headed for a crisis that could have been avoided.

“The School Committee could have solved this problem,” Flynn said.

Like a lot of communities, the heart of the neighborhood was in its high school and its sports teams.

“I used to go over to White Stadium as a kid, and I used to see Southie High play football. And that meant an awful lot,” Flynn said. “That inspired pride, sense of community, and we were broken hearted whenever they lost.”

Flynn said Judge Garrity and those who supported busing failed to understand why the South Boston High School was important to the community’s identity.

“Now we’ve got this judge, or this group of people, come in and say ‘oh by the way, what you’ve believed in all your life, what you grew up with all your life, that’s not going to happen anymore. We’ve got another plan for you,’” Flynn said.

Generations of residents attended South Boston High School. Sons and daughters could see the names of their parents on walls and in trophy cases. Jerome Winegar said few Southie High graduates were encouraged to enroll in college before he became headmaster in 1976.

“We had a sheet metal shop there, and you’d just go take the sheet metal program there and you’d find a way to make a little money,” Winegar said. “That’s how kids were treated there.”

On occasion, when a student got a chance at going to a good college, the actions of school officials could become insidious, to the point of outright sabotage to keep a student from escaping the neighborhood.

When Flynn graduated in 1959, he was recruited to play football for Syracuse University, Winegar said the former mayor once told him. Though he was an exceptional player, his dreams were torn apart when a guidance counselor told the coaching staff at Syracuse that Flynn wasn’t smart enough to play for the Orangemen.

“Ray told me that story years ago,” Winegar said. “He never forgot that.”

South Boston’s efforts to protect its  neighborhood from outsiders quickly unraveled into chaos. Groups like ROAR did not advocate for violence. But, some of its leaders like Elvira “Pixie” Palladino of East Boston are quoted in Anthony J. Lukas’s book “Common Ground” taunting blacks by calling them “pickaninnies” and using racial slurs like “jungle bunnies.”

“We weren’t [racist],” Johnnene said, though she acknowledged that some of the things fellow ROAR member Pixie Palladino said were “harsh.” She also said that inside Palladino had a “heart of gold.”

Many of the working class Irish and Italian families that protested busing felt that they were just as disadvantaged as the black children who were being bused from overcrowded under-performing schools.

They viewed the program as equally offensive to both races. Johnnene said that had it only been black kids who were being bused, “it wouldn’t have been fair to them” to have to go across the city to attend school.

Flynn argues that it was only a small number of people who were throwing rocks and attacking black children. He said they were “embarrassing to all of us,” but there was little he could do to stop them at the time.

“What was I going to do, pick up a person and carry them down the street?” Flynn said. “I mean, these people, if they did that, they were arrested and they paid the consequences.

“But to categorize the whole community of 38,000 people with the actions of five or six people leading a crowd that was frustrated, that was in pain because they saw their children losing the opportunity to get a good education, losing their future,” Flynn said. “It was frustrating because what you’d do is you’d agree with them, you’d believe them, you love them, and at the same time you’re unable to do anything for them.”

Though Flynn was a voice for the anti-busing movement, he wasn’t willing to lose old friends over the crisis. In 1974, Joseph Burneika worked in the Office of Implementation, a working group that figured out the logistics for the second busing plan within Mayor Kevin White’s administration. He first met Flynn as a senior at Boston English High School, where Flynn served as a substitute teacher in the mid 1960s. When the two would bump into each other, busing never came up in conversation, Burneika said, even when he became a spokesman for the Boston School Department.

“I think he respected that I had a job to do,” Burneika said. “If he was going to interfere with that, it would be at the court level. He wasn’t going to bother the worker bees.”

Though Burneika worked at the office that managed the busing program and supported desegregating the schools, he was against how the plan was structured. Burneika said he sent numerous letters to Judge Garrity’s court appointed “masters,” Robert Dentler and Marvin Scott, suggesting that the program be implemented slower or in phases. He suspects that they never passed the messages to Judge Garrity and that they have escaped much of the blame for the failure of the program.

Dentler and Scott have died, and Burneika, who serves as interim director of Catholic Charities, now views the busing program as an abject failure.

Flynn was one of the few members of his high school class to leave South Boston after graduation. He was a star player for Providence College and was drafted by the Boston Celtics. He returned to South Boston after briefly serving in the army, the state probation department and Hubert Humphrey’s failed presidential campaign in 1968. Flynn’s first chance to represent his neighborhood was when he was elected as a state representative in 1972.

In the second academic year of busing, Judge Garrity hired Winegar as headmaster of South Boston High School. Winegar said he was widely disliked by South Boston residents, including Flynn.

Shortly after Winegar arrived, the South Boston High School football team was invited to play a game at Boston University. Winegar said he objected because BU only had seating on one side of the field, and he thought it was ripe for trouble.

Just as expected, a fight broke out, and South Boston was banned from high school playoff tournaments unless Winegar could guarantee the crowd’s safety.

Winegar asked Flynn, the school’s former star basketball player, for help. Flynn got a group together, dressed in red and blue arm bands to watch over the games.

Later in the year, the hockey team made it to the semifinals of the state tournament. The game went into overtime, and a referee called a penalty on what would have been the winning goal. Suddenly, the fans started getting rowdy, Winegar said.

“All these people jumped up to their feet and started yelling,” Winegar said. “Ray Flynn and company stood up in front of each section and said, ‘sit down.’”

South Boston won the game but lost in the state finals, Winegar said.

“From that point on, every time there was anything of importance, I invited him to come,” Winegar said.

Flynn was elected mayor in November 1983, and he was in South Boston High School the following day. At the time, there were persistent rumors that the school would be closed.

Winegar saw a little girl approach the mayor-elect and ask if his election meant the school would stay open.

“Ray Flynn said, ‘you bet,’” Winegar said.





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