But, in the end, he was still a state representative from Dorchester whose demographic profile was unlikely to ignite any transcendent grass-roots momentum, and who would inevitably be saddled with the impression that he was beholden to organized labor.

Walsh’s seasoned team of campaign strategists knew his strengths: affability, a salient personal narrative of redemption, a doomsday army of union members who would trounce any rival in the manpower game.

To counter that image, the campaign needed a resounding message that the Dorchester Democrat was bigger than that, that he could be a leader for the whole city.


The Walsh strategy, which carried him to victory Tuesday over City Councilor John R. Connolly to be Boston’s 48th mayor, was twofold: capitalize on his strong support in union households while rendering him as a progressive, populist figure empathetic to the city’s changing electorate.

Two days after winning the Sept. 24 preliminary, Walsh held a “Women for Walsh” meeting at Old South Church in Copley Square, relying on social media and his swelling political network to draw women from across the city.

“We wanted to make sure that people understood that we were a diverse campaign, that we had women, we had people of color, that it was more than just a ‘Dorchester guy’ running,” said one of Walsh’s senior campaign advisers.

“Marty was a virtual unknown out of his district,” another Walsh senior adviser said. “We had to send a clear message to the public about his cachet, make a statement to the public of him having the je ne sais quoi of a mayor.”

A series of conversations with operatives and supporters on both sides of the mayoral race — who were assured their names would not be used in order for them to speak candidly — laid bare the Walsh camp’s frustration with an inability to tamp down what it viewed as inordinate coverage of his strong ties to labor. In the Connolly camp, there was disagreement over how Connolly should counter Walsh’s momentum and expand beyond a ready-made base of voters who identified Connolly as the more effective candidate on education.


Connolly and his small coterie of advisers hadn’t truly seen Walsh coming. Connolly had said privately that Walsh was the candidate he’d hoped to face. The pairing of two Irishmen would drain the race of its most powerful potential narrative: of a changed city, eager for a changed leadership.

“They thought that if they went into a final election against a Dan Conley or a Marty Walsh, that they would grab the liberal mantle,” a Connolly campaign adviser said.

Much more frightening to the Connolly retinue was the prospect of drawing a foe like Charlotte Golar Richie, who finished third in September and could have posed a history-making appeal to be Boston’s first minority and first female chief executive.

Landing Golar Richie’s support was a crucial juncture on Connolly’s general-election roadmap, particularly after Walsh had already wrapped up the support of two other mayoral contenders, Felix G. Arroyo and John Barros.

Both candidates had lobbied hard. Walsh met with Golar Richie at her Meetinghouse Hill home one night until 1 a.m. Connolly visited her there four times, in what one campaign official called “a courtship” of daily calls and texts.


Then in early October, Connolly was called to a meeting with some of Golar Richie’s key aides — Darryl Smith, Gary Webster, and Brooke Woodson — field organizers with roots in Mayor Thomas M. Menino’s machine.

They met late on a Thursday, in the back room off the kitchen of a small Dorchester restaurant. Moments into the meeting, Golar Richie called and gave Connolly her verdict. Her aides would back him, but she would endorse Walsh.

Twenty-four days before the election, the news devastated the Connolly campaign.

On the heels of Golar Richie’s endorsement, other state and city officials of color began lining up behind Walsh as well, signaling to black and Latino voters where they should come down in a race between two white Irish guys.

“He reeled off nine endorsements of people of color and that’s what the race became about,” said one top Connolly campaign official. “It catalyzed everything.”

At the heavily staged Oct. 12 event rolling out the Golar Richie endorsement, a campaign aide waved reporters out of the way outside Dorchester’s First Parish Church. The campaign desperately wanted the image that would grace television ads, signs, and fliers: The iconic tableau of a smiling Golar Richie, Arroyo, and Barros strolling alongside a candidate who could appeal across neighborhoods, and who had the momentum.

“These endorsements validated Marty in a way that we couldn’t have done otherwise,” one Walsh adviser said. “Most of these people had an intimate knowledge of both candidates, and every one of them chose Marty, and that speaks to his character. And that was one of the biggest differences in the campaign. They trusted him.”


Connolly may have started the race as the front-runner — the first to announce and a leader in the polls — but Walsh was wielding clout that belied his likeable, local-guy image.

“He had more money. He had more bodies,” the Connolly campaign official said. “And he had more power.”

Connolly knew he had to regroup. He needed to present a more well-rounded candidacy broadening his rhetoric beyond education policy, and injecting more of his biography. And most of all, he needed to stanch the bleeding in communities of color.

At an Oct. 21 event at Roxbury’s Hibernian Hall, eight speakers lauded not just Connolly’s policy prescriptions for communities of color, but the work he’d done for them in the past.

The campaign also sought to capitalize on what they believed was a hidden asset. At a downtown event the following week, Meg Connolly, the councilor’s photogenic wife, spoke emotionally in defense of her husband in the face of labor-backed efforts to typecast him as a “son of privilege.” Through tears, she described how Connolly was by her side as she fought lymphoma shortly after they were engaged.

But by that point, some believed Connolly had already lost ground to Walsh.

An internal Connolly poll showed that Walsh had pulled even, the candidate told his campaign finance committee at an Oct. 28 meeting.

When one fund-raiser asked whether the decision-makers intended to broaden the overarching message beyond education policy, campaign manager Nathaniel Stinnett, according to two people who were present, replied that while he understood the sentiment, “We don’t run on gut, we run on metrics.”


Polling had begun to show that their options around changing the message were limited.

“The only narrative that worked was the union money, and that’s when they decided to get to that pivot,” said one Connolly adviser. “But, by then, Marty was seen as the nice guy, and the union money argument only worked with people who were predisposed to think that way.”

Compounding tensions over the campaign narrative were concerns that Connolly had spent valuable time right after the September preliminary election too preoccupied with fund-raising as he struggled to close a significant financial advantage that outside groups were giving Walsh.

Even though Connolly, too, was a beneficiary of outside spending, from education reform groups, he knew he had to find a way to compete against the onslaught of cash on the Walsh side.

To do so, Connolly had sharply curtailed his public schedule immediately after the preliminary election, hitting the phones and dialing for dollars. “We literally just went immediately overnight into fund-raising mode,” said the Connolly campaign official.

From a financial perspective, it worked. His fund-raising during that period was jaw-dropping. In the first 15 days of October, he pulled in more than $600,000, nearly tripling Walsh’s take and raising expressions of incredulity among Walsh aides. “It was stunning,” one Walsh strategist said. “Then we were like, OK, where’s it coming from?”

State campaign finance records from that stretch bear out anecdotal evidence of the chatter in political circles. Longtime allies and friends of Menino were backing Connolly, part of a larger trend of the city’s legal, real estate, and financial services sectors voting for the West Roxbury councilor with their wallets.

It might have been the single most impressive burst of political fund-raising in the city’s history. But it came at a cost. As Connolly worked the phones, Walsh outgunned him in the neighborhoods, sewing up pivotal endorsements and establishing the lead in the grass-roots voter contact that has come to predominate in Massachusetts politics.

Walsh was also spending his time making a more emotional appeal, pitching working-class neighborliness while playing the inside game with the help of his establishment allies.

“He was brilliant — playing the underdog, playing the class divide,” said a top person in the Connolly campaign. “At the very same time, he’s pulling every power lever there is, moving the race. I don’t know what we could have done different.”

All the while, Walsh was piling up support from labor, both within his campaign and outside it, with national groups feeding more than $2.5 million in independent spending on his behalf. The support, however, drew scrutiny, and Walsh staffers raged against what they felt was a media-driven narrative that he was a one-dimensional politician.

“Clearly, the campaign’s desire was not to talk about labor every day. But our desire and the media’s desire were at loggerheads. So, sooner or later, we had to embrace it,” another top adviser said.

In the field, they already had, using their edge in boots on the ground to begin focusing on neighborhoods around Connolly’s base: West Roxbury, Hyde Park, and Jamaica Plain.

“Particularly over the last three weeks, we just buried them with bodies. Every weekend, every night, we were calling them, we were knocking on doors,” one Walsh adviser said of the incursion into the city’s Southwest corridor.

“And it worked, because Connolly was spending a lot of time in West Roxbury, and he shouldn’t have had to spend any time there,” he said.

When Election Day arrived, Connolly made stops in West Roxbury and Roslindale, and spent much of it in Hyde Park and Roxbury, making a final bid to prevent Walsh from running up the score in those two neighborhoods.

But the drama was unfolding downtown.

Early figures augured well for Connolly — higher-than-expected turnout in city’s close-in neighborhoods, the Back Bay, Beacon Hill, yuppie parts of Charlestown, the West End, North End, and South End. At a West End campaign stop three days earlier, Connolly had dubbed the internal neighborhoods “my firewall.” The early numbers led Connolly’s campaign to think they just might pull it off, while sowing anxiety on the Walsh side.

Walsh, looking at the numbers after 3 p.m., dialed the boiler room for Matthew J. O’Neil Jr., who with Thomas J. Keady Jr. had been Walsh’s decision-making nucleus.

Walsh’s message: get field workers knocking on every door in his Dorchester base and in Roxbury, where they hoped the endorsements from black politicians would pay dividends.

In a race where Walsh had benefited from a perceived class divide between the candidates, he was betting that working- and middle-class neighborhoods would offset Connolly’s strength in the higher-income wards.

Within a half-hour of the polls closing, Connolly’s camp knew he was in trouble. They had calculated they could not lose Hyde Park by more than 10 percentage points, and needed to win West Roxbury by 30. “You only needed to see two or three precincts from either one to know,” a Connolly campaign adviser said.

Connolly’s home neighborhood hadn’t delivered for him as dramatically as he needed. Walsh’s dealt the final blow.

Watching from his 15th-floor room in the Park Plaza, Walsh saw a lead of about 4,000 votes, with only 13 precincts left to report. One of them was his Savin Hill precinct, where the polling place is across from his house, at a high school he helped bring to the neighborhood.

Within hours, President Obama was calling to offer his congratulations. Marty Walsh was going to be the mayor of Boston.

Jim O’Sullivan can be reached at jim.osullivan@globe.com. Follow him on Twitter @JOSreports. Stephanie Ebbert can be reached at s_ebbert@globe.com. Follow her @stephanieebbert.