On January 2, 1984, Raymond L. Flynn marked his first day as mayor of Boston by returning to where he had launched his campaign for the office eight months earlier. Just hours after being inaugurated at the Wang Center, he went to a community center near the West Broadway public housing development in predominantly white South Boston. At the suggestion of his co-finalist in the 1983 election, Mel King, he added one more stop, in a predominantly Black Dorchester neighborhood, at the Franklin Hill development.

The itinerary was a show of bridging divides: by race and income, even between downtown Boston and the city’s neighborhoods. And, when the get-together at Franklin Hill Avenue went live on TV, the children huddled around the new mayor could see themselves on a monitor, bridging yet one more divide: between spectators and newsmakers.

Don Gillis, a tenant organizer who helped plan the appearances, was crossing his own bridge, from activism to City Hall, where he would serve Flynn as a senior advisor. A Roslindale native who grew up in Worcester, Gillis went to college at Villanova University, which led to work with young people at a Boys and Girls Club in Philadelphia. Back in Boston, he did outreach and organizing in the Fenway and Mission Hill areas, leading to his work with residents of public housing.

Following his years in the Flynn administration, Gillis earned a PhD in sociology from Boston University with a dissertation that he later expanded into his new book, published by Fordham University Press, “The Battle for Boston.” More than forty years after inauguration day, Gillis looks back at 1983 as a triumph for Flynn and community organizers over “racism and downtown power brokers,” but also a pivot to a more progressive trajectory that continued for decades to come.

“It was a critical election that had a profound transformation of power relationships in the community,” Gillis said in a remote interview last month. “And that hasn’t really occurred since.”

Flynn’s campaign launch was also a nod to deteriorated conditions that had led to Boston’s public housing—under his predecessor, Kevin H. White—being placed under receivership. But the setting was also in stark contrast with a more typical backdrop for campaigns – the Parker House, a landmark hotel up the street from Boston’s old city hall.

According to Gillis, the announcement setting, close to Flynn’s working-class roots in South Boston, transformed a campaign staple into a different, more personal message. As Gillis put it: “I’m about poor people, about the neighborhoods and about solving problems out here. And, so, I’m not going to the Parker House. I’m going to hold my announcement right here.”

But, in another remote interview last month, Flynn himself, at age 85, characterized the transformation as more than a sum of candidates and campaign branding.

“The city doesn’t change unless the people want it to change,” he insisted. “That’s what the story is about.”

In late May 1983, following a record sixteen consecutive years as mayor of Boston, White announced his decision not to seek a fifth term, turning a possible sequel into a whole new pilot. Whoever became the next mayor would also lead a city dramatically changed by a period of upheaval, with racial tensions and violence coming to a head when desegregation of the Boston Public Schools began in 1974.

With violence rippling out from schools into changing neighborhoods, White presented himself as an impartial force of moderation, denouncing violence, yet signaling differences with desegregation remedies ordered by a federal court. A decade later, with racial hostilities more confined to neighborhood streets and parks, Flynn’s approach was to engage, even making house calls to families who were being victimized.

As Gillis relates, Flynn also strengthened support for response to hate crimes from the Boston Police Department’s Community Disorders Unit, already headed by his longtime South Boston friend, Francis “Mickey” Roache. Between the police work and media coverage that placed families and the mayor on equal footing, the effect was to narrow the divide between neighborhoods and city hall—along with, as Gillis demonstrates, reducing violent hate crimes.

“And I think that’s what Ray Flynn knew,” Gillis explained. “You couldn’t hide behind it and say there’s nothing happening, and everything’s wonderful. You had to confront the issue head on. And he did. And it had an impact. I think it had a dramatic impact.”

Flynn traced the approach back to his experiences long before his political career, while he was playing basketball with Black teammates, still on his way to stardom at Providence College and becoming an NBA draft pick in 1963. Together with his teammates, Flynn was already crossing boundaries as they took to the courts around the city.

“I knew the city, not from a political point of view, but from a people point of view. And they knew me,” Flynn recalled. “So, it didn’t come as any surprise that there was unity in the city just waiting to step up to the plate, waiting to come forward. And I always thought to myself, there were more things in common that unite people than the narrow issues that divide people.”

Above, Mayor Flynn at event for redevelopment of the Pierce Building in Uphams Corner (1984) by the Dorchester Bay EDC. Chris Lovett photo

As a state representative from South Boston from 1971-78, Flynn was known beyond his district mainly for opposition to the court’s desegregation plans and his stance on abortion. He was the co-sponsor of an amendment filed with West Roxbury’s Charles R. Doyle to block state funding of abortions, a measure commonly referred to as the “Doyle-Flynn Amendment.”

After his election to Boston’s all-at-large City Council in 1977, Flynn highlighted other agendas being advanced by grassroots organizations around Boston, anything from help for the homeless to reducing jet noise, or restoring the rent control protections that were pared back in 1975 by passage of vacancy decontrol. By 1983, Flynn was also backing a local measure, championed by fellow councillor Bruce C. Bolling, to require “linkage” fees from large development projects—often enabled by zoning waivers—to fund affordable housing and job training for city residents.

As candidates for mayor, Flynn and King were the most closely identified with progressive agendas and grassroots alliances. But, among many political pundits, the early favorite before the preliminary election was David Finnegan, a former School Committee member from West Roxbury. Originally from Dorchester’s Neponset area, he was also a popular talk show host on WBZ radio before launching his campaign. While still expecting White to seek a fifth term, Finnegan cast himself as a foil to the incumbent. After White’s decision not to run, Finnegan was recast as more of an insider, endowed—or saddled—with the incumbent’s downtown stature and campaign funding pool, much of it from developers and large property owners.

Even before 1983, grassroots organizations had been exerting influence with campaigns to increase hiring of Boston residents on the city payroll and publicly funded construction projects. In 1981, they successfully promoted a ballot measure that would create district representation on the City Council and School Committee—two bodies elected at-large since 1951 and increasingly mismatched with the city’s growing diversity. But, as with rent control, the groups backed agendas with multi-racial appeal, highlighting economic gaps amid the growth in the Boston area’s “knowledge economy.”

One transformation in 1983 took place when members of the Massachusetts Tenants Organization (MTO) departed from the activist norm of voter engagement, which stopped short of explicitly endorsing candidates. Lew Finfer, an MTO organizer at the time, said members reasoned that the only way to surmount city resistance to full restoration of rent control was to get more supporters elected.

Above, Ray Flynn greeted voters at a March 1984 community forum at McKeon Post in Dorchester. Chris Lovett photo

“David Finnegan was definitely in first place,” said Finfer, “so one of our concerns was that if we didn’t endorse either Flynn or King, or if we endorse both of them, then we wouldn’t be helping one or another enough. And David Finnegan might become mayor, and he had gotten money from landlords.” The group endorsed Flynn, partly because, as Finfer noted, he was “more present” in the group’s rent control efforts with the city council.

What neither MTO nor most political observers had expected was that, in the preliminary election, Flynn and King would emerge as the finalists, with Flynn ahead by only 270 votes. Though the more progressive votes were split, Flynn also got strong support in predominantly white neighborhoods with different political leanings—including South Boston, Hyde Park, Roslindale, West Roxbury, and some parts of Dorchester outside of Neponset.

As the fourth-place candidate in the preliminary, former city councillor Larry DiCara, put it, Flynn’s movement was “two-headed,” combining progressives with trade union members and voters who opposed busing and abortion—all united by disenchantment with White.

“The surge of support for Mel and for Ray,” DiCara concluded, “was anger at Kevin White and how much Kevin White had focused on the downtown, as opposed to neighborhoods. Kevin was very much a top-down kind of guy, and both of them proclaimed they would be bottom up kind of people.”

Despite the mixed support behind Flynn in both election rounds, Gillis plots a decidedly progressive tilt in his policies as mayor, especially on race relations, affordable and transitional housing, tapping more benefits from Boston’s large development projects, as well as overcoming discrimination and disinvestment by banks.

In his first year as mayor, Flynn spearheaded a push to restore tenant protections and limit the accelerating pace of condo conversions. Though the regulations adopted under Flynn would be overturned by a statewide referendum in 1990—which failed to carry in Boston—policies such as linkage and resident hiring would endure, or even be strengthened, by Flynn’s successors.

In early 1985, reports of an expected Boston Redevelopment Authority (BRA) plan for Dudley Square boosted hopes for improvement in Roxbury, along with neighborhood concerns about displacement and a lack of community participation.

By 1986, the Flynn administration changed direction by supporting a new nonprofit, the Dudley Street Neighborhood Initiative (DSNI), that would shape development of vacant land through planning and even powers of eminent domain. To secure that authority for DSNI in the Dudley Triangle area, Flynn and BRA director Steve Coyle had to overcome strong resistance from a BRA board still dominated by Kevin White appointees.

Flynn prevailed, but only after a heated exchange with board members who were summoned to his office. The result transformed vacant lots and areas blighted by dumping into new affordable housing and community gardens, with a new community center added later, under Flynn’s successor Thomas M. Menino. If the results marked a shift from the focus on downtown growth, Gillis argues, they also transformed the tenor of relations between the mayor’s office and the community, including many nonprofit development corporations and advocacy groups.

“Flynn had faith in the community, that they could be the ones who could take the lead and rebuild in the community,” said Gillis. “And so, it isn’t something you would see. And in fact, it’s never happened in another time in the country – that eminent domain authority was given to a community group.”

Likewise, the activist background of other top Flynn aides—including Ray Dooley and Neil Sullivan, would play a larger role in everything from neighborhood development to city services and the desegregation of public housing in South Boston. There was fierce pushback in South Boston, but Gillis details the Flynn team’s engagement with the community, guided by activist know-how and aides with strong neighborhood ties.

Because of the change in focus on neighborhood development and the collaboration with community groups, Gillis distinguishes Flynn from the “growth machine” model that his predecessors had followed since 1949. Given the decades of policies favoring growth, assisted by public dollars and tax breaks, or even displacement of local residents, Gillis labels Flynn’s role from 1984 on as both redistributive and transformative. And he shows how the pattern continued, even as it would continue to be disputed, whether by the development sector, affordable housing advocates, or neighbors pushing back against higher density.

Jim Vrabel, author of “A People’s History of the New Boston,” assessed Flynn’s impact by writing, “Even though it often amounts to crumbs, people should be glad when ‘politics of equity’ politicians like Flynn come around to share more of the pie that capitalism cooks up for cities with the poor and working people who still live in them.”

But DiCara noted that there was a less positive impact on growth in housing and the tax base. “You can make the case that the zoning changes that went into effect in the eighties and nineties down-zoned the city,” he said, “and have made it more difficult for small housing to be built.” The current mayor, Michelle Wu, struck a progressive chord by calling for abolition of the BRA’s successor, the Boston Planning and Development Agency (BPDA), in her 2019 report on Boston’s “broken development process.” But the report also cited hurdles for developers that made the approval process more costly and less predictable.

Boston’s more progressive local policies evolved over decades of growth in the region’s “knowledge economy,” with its own dependence on federal money. In the face of new economic and political challenges, and even calls for easing up on affordability measures, Gillis maintains that Boston mayors should stay a progressive course.

“We’re in a transitionary period, in many respects, a result of the economic factors that are beyond any one leader’s control or any one mayor’s control, that they have to respond to – and that I think they’re responding to,” he said. “But, to say that the answer is to cut out affordability, to cut out opportunities for people to stay in the city of Boston, to have a shot at living in a decent home in a decent neighborhood, that is really not the way to go.”

As Gillis relates in his book, Flynn’s results with the BPS and the Police Dept. are more conflicted. He supported the 1991 referendum to replace the elected school committee with an appointed board. The measure passed, but with a margin dwarfed by his re-election spread. Thirty years later, after mixed results with committees appointed by his successors, almost 79 percent of Boston voters approved an advisory measure calling for return to an elected committee.

After citing different views on school governance in US cities, Gillis concluded, “Mayoral takeover is not a solution. It is a strategy on behalf of a coalition, which varies significantly from city to city and from time to time.”

As with his predecessors and successors, Flynn encountered problems with conduct and performance at the Boston Police Department. After an in-depth review by The Boston Globe in 1991, there would be more scrutiny from a committee convened by Flynn and headed by the prominent legal authority, James D. St. Clair. The ensuing report in 1992 made news by calling for the replacement of Flynn’s appointed police commissioner, Mickey Roache. The report’s focus was mainly systemic, but a standout in shortcomings highlighted by The Globe was the “Stuart case” of 1989.

As first depicted in highly sensational media coverage, the case was about an alleged carjacking in which a pregnant white woman, Carol Stuart, was killed in a shooting by a Black man, who also shot her husband, Charles Stuart. They were a married couple from Reading, and the incident took place right after a birthing class at Brigham and Women’s Hospital, in the nearby Mission Hill neighborhood of Roxbury.

As with other racially charged events, Flynn quickly responded, joining with Roache to meet with affected family members at hospitals. What followed were aggressive searches by police for a suspect in Mission Hill and, eventually, questions about whether a more effective investigation would have revealed sooner that Charles Stuart had been less a victim than a perpetrator and hoaxer.

At the neighborhood level, there were questions about why the police and the media responded to a local crime with more alacrity when the victims were white suburbanites. In the view of then-Globe columnist Mike Barnicle, the graphic photo of the murder victim—on a Boston Herald front page—was transformative in a different way: as a trigger for rage at what he said could “rock the city to its core.” As formulated in the headline for another Globe column, the real story was “Urban Crime, Suburban Fear.”

Mayor Flynn spoke from the podium at an event outside the recently-opened B-3 police station on Blue Hill Avenue in Dorchester, circa 1987. City of Boston photo

Gillis’s book faults police actions in the Stuart case, and his interview with Menino surfaced the criticism that Flynn had “overreacted instantly.” But Gillis also faults the news coverage at a time when Boston’s media landscape was defined less by city limits than the metrics and mindset of a regional television market, coupled with the more traditional co-dependence between reporters and police. In the frenzy around the Stuart case, the local perspective elevated by the immediacy of television during Flynn’s 1983 campaign and after would be upstaged—by the personal drama of suburban victims and the typecasting of an urban neighborhood.

When asked in an interview whether he would have done anything differently in the course of the Stuart case, Flynn pivoted, zooming in on memories of neighborhood parks and kids whose desire to play was greater than what they could pay for equipment—or a bite to eat.

“I saw so many opportunities that I could have done more to help people, if I only had access to more money,” he reflected. “I saw kids going down the park. They didn’t even have money to buy a glove. And I’d get them one – I’d pay for it if I could. But we’d have some other problems. And kids would have sandwiches, bringing them down, playing ball, and all that. Other kids would come down. They didn’t have anything to eat. But I still have that: I can’t pass a homeless person without giving them a buck. But that would be what I didn’t do a good job on: I didn’t have enough money to give to the kids that needed it.”

Mr. Gillis will discuss his book on June 16, 6p.m. at the Codman Sq. branch of the BPL, 690 Washington St., Dorchester.