How the Josh Kraft campaign unraveled

speedy forward to September, and it was another television spot in which Kraft officially called it quits.

“I got into this to make an impact,” Kraft said in an interview with WCVB on Thursday, but the ugly campaign had taught him he could do more from the outside. “When I kept looking at the next eight weeks… I realized, ‘Wow, I can do more.’ I can make a better impact.”

Kraft carried significant advantages for a challenger in a Boston mayor’s race: name recognition, a long history of philanthropy and nonprofit work, experienced political staff, and a fat checkbook. But his campaign was marked by repeated missteps and stumbles — messaging mistakes and staff shakeups, aggressive attack ads that did not quite land. That all played out against a national political environment that favored his opponent from the start.

It was those factors — a first-time candidate who never seemed to get his political sea legs; an incumbent who relentlessly attacked him, no matter how far ahead she got; and a federal administration that enabled her to emerge as a model for Democratic resistance — that ultimately led to last week’s shellacking.

When results came in from Tuesday’s preliminary election, Kraft had earned a spot in the general election, but the victory was Pyrrhic. Wu won an astonishing 264 of the city’s 275 precincts, sweeping most of the white, conservative neighborhoods that should have been fertile terrain for Kraft, as well as the communities of color where his campaign had worked hard to make inroads. She beat him in the corners of the city where he spent years building relationships as the leader of the Boys and Girls Club of Boston and also in the tony waterfront neighborhood where he moved two years ago in anticipation of a mayoral bid. Wu’s dominant performance left him a vanishingly narrow path forward.

On Thursday Kraft exited the race, pledging to serve Boston in other ways. He said he would devote his campaign resources, $3 million to start, to addiction and recovery organizations, and promised also to revitalize a prison reentry program he had supported in the past. Kraft did not respond to an interview request from the Globe.

“We could spend the next eight weeks politicking — with harmful rhetoric or nasty attack ads,” he wrote on Instagram. “Or we could get back to what really matters.”

From the start, the conventional wisdom went that Kraft would have a harder time beating Wu if Donald Trump won the White House. In a blue city like Boston, the thinking went, a white man from a privileged background would struggle all the more to topple a barrier-breaking woman of color if she had a foil in the White House she could use to position herself as a national progressive leader.

Yet Trump won in November, and in February, Kraft announced he would run, launching his bid at Prince Hall in Dorchester as a nod to his work in the area over the years as head of the Boys and Girls Club.

That very first day, Boston political analysts said, he made a critical mistake. Before he had fully introduced himself to the electorate, he went on the attack. Wu “just does not listen,” Kraft said; she had “not risen to” the city’s challenges.

The mayor quickly shot back, taking aim at his newfound residency in Boston, where he had worked for decades but not lived until 2023. “I welcome Josh Kraft to the city,” Wu said.

Soon after came one of the days that defined the campaign — a day Kraft had no role in. In early March, Wu spoke before a GOP-led congressional committee, dodging traps and standing firm in defense of the city’s immigration policies, with Ash Wednesday ashes on her forehead and her newborn daughter Mira in tow. The image resonated.

Back home in Boston, Kraft joined those gathered on City Hall plaza to cheer on the mayor as she squared off against Republicans. Before the event started, Kraft briefly addressed reporters to express his support for Boston’s immigrant communities and condemn Trump’s mass deportation efforts. He also slammed Wu for spending hundreds of thousands of dollars on an outside law firm to prepare for the grilling in Washington.

Later, as Wu’s testimony continued and other speakers addressed the crowd, Kraft stood alone with his hands in his pockets, quietly taking in the scene.

Wu had started the year as a powerful incumbent, but “she came back from Washington a hero,” said Joyce Ferriabough Bolling, a longtime Boston political strategist. For Kraft to attack a mayor seen as the city’s proud defender “killed him,” she added.

“The campaign really started off very wrong,” Ferriabough Bolling said. “If you want to punch and kick, make that toward the end or not at all.”

As the campaign wore on, Wu took advantage of more opportunities to face off against the Trump administration, a political tactic that won her support from Boston voters and grew her national profile.

Meanwhile, Kraft had to contend with his family’s ties to a president who is deeply unpopular among the voters Kraft was trying to woo. Robert Kraft had been a close friend and financial supporter of the president. And some of the elder Kraft’s associates wrote checks to the campaign, making those ties hard to ignore.

For some on Kraft’s team, the focus felt unfair.

“The media wanted to focus on Donald Trump and Robert Kraft and the Patriots when Josh really wanted to be a mayor for the city of Boston,” said William Berlin, Kraft’s policy director. Wu and her allies “want to portray him in one way, as just this wealthy man that just wants to run for mayor to gain power, when in fact, he is the most kind, thoughtful, humble individual.”

Kraft’s wealthy background meant that even when he had a strong message, he was not always the right messenger. Here was a candidate rightly pointing out that after four years of Wu’s tenure, Boston Public Schools continued to struggle and housing costs in the city remained sky-high. Yet he had sent his children to private school and lives in a $2 million condo on the waterfront, while his opponent sends her kids to BPS and shares a more modest duplex with her mother.

Kraft “had a credibility problem,” said Katie Prisco-Buxbaum, a political consultant who ran Andrea Campbell’s unsuccessful Boston mayoral campaign in 2021.

“It’s hard to separate the message from the messenger,” she said, and Kraft “failed to define himself really early on. He kind of let [Wu] define him.”

Kraft tried to hammer Wu on the rising cost tag of her plan to redevelop White Stadium for BPS students in partnership with a new, professional women’s soccer team. But it wasn’t enough to sway voters. Polling from Emerson College showed that despite his campaign’s focus on the issue, public sentiment barely budged: In February, 53 percent of likely voters supported Wu’s project; in September, 48 percent backed it.

Kraft also never fully captured the support of business leaders — a group that, by virtue of its skepticism of Wu, could have proven to be his strongest ally.

While many in the real estate industry wanted someone to unseat Wu, few, if any, openly supported Kraft. Business leaders had been wary about Kraft’s candidacy; while he did a lot of good as a nonprofit leader, he didn’t come across as a natural politician, and they worried he couldn’t go toe-to-toe with a seasoned campaigner like Wu.

Their worst fears were confirmed early on as they saw Kraft at fund-raisers and on the campaign trail, business leaders said. He lacked the charisma and policy chops to be a serious mayoral candidate, so much so that some people encouraged Boston developer Tom O’Brien to jump into the race.

Kraft’s team defended his campaign style.

“You can’t expect somebody who is not a politician to come in acting like a politician from day one,” said Marcus Johnson, who worked as field director for the campaign. Johnson said Kraft connected well with voters. “Every time I saw Josh speak, I was amazed. … My heart was warm because I could tell he was genuine.”

Aside from the broad message of Kraft’s campaign, there were operational missteps big and small. The campaign lacked legally mandated workers compensation insurance. Trucks and billboards of a pro-Kraft super PAC parked illegally in bike lanes and cross walks, earning social media mockery.

Early on, donors were asked to a campaign fund-raiser for Kraft with an invitation that featured not Boston’s skyline, but New York’s.

The invitation was not created by the campaign. But the gaffe nonetheless reflected poorly on a candidate who had already been accused of not really knowing the city he wanted to represent.

Months later, when mayoral candidates were asked at a forum which city ward they lived in, Kraft admitted he didn’t know. Sitting down the table from him, Wu held up three fingers — Ward 3.

These self-inflicted wounds didn’t help, political analysts said.

“There were a lot of sloppy mistakes that frankly just fed into what people thought about him,” Prisco-Buxbaum said. “He had kind of a long shot to begin with, regardless of how much money he spent on it. But do I think he could have done better? Yes. He could have made it at least a competitive race.”

By the summer, prospects still looked dim for Kraft, even as he ramped up spending and began to blanket the airwaves with television ads. Two advisers left the campaign.

Then, in late July, a Boston Globe/Suffolk University poll showed Kraft trailing Wu by a decisive 30 percentage points. It was the first public poll of the race in months, and it landed with a thud. Kraft had spent millions of dollars and somehow found himself no closer to unseating the incumbent.

“The poll was the killer,” said Bob Rivers, executive chair of Eastern Bank, who has long supported Wu but also gave the maximum donation of $1,000 to Kraft. “At that point, people, if they hadn’t hedged their bets before, they were certainly hedging them today, because they began to increasingly realize that the mayor was still going to be the mayor.”

In public, campaign advisers insisted they still had time to reverse the tide. But Kraft’s chances were slipping, and it was made evident by a loss of faith from the donor class. A super PAC supporting Kraft had raised $1.2 million in May, and more than $550,000 in June. In July, the PAC pulled in just $115,000; by August, the haul fell to just $13,000.

By Labor Day, the roles had begun to feel very familiar for the two leading candidates. Kraft marched in the parade with a small crowd of guys from Iron Workers Local 7, one of the unions that had endorsed him. Wu spoke from the stage on City Hall plaza, the crowd greeting her as if she were a rock star.

Less than a week before the election, as he made a last-minute pitch to voters in a televised mayoral forum, the news broke that Kraft was parting ways with two of his closest advisers, Will Keyser and Eileen O’Connor. The married couple had been working for him since before his launch; their departure, so close to the election, signaled distress. Just days before the election, a new Emerson College poll found Kraft trailing Wu by a staggering 50 percentage points, another blow.

The remaining staff worked hard through preliminary Election Day. When the results revealed a punishing margin for Kraft, some were shocked.

“I was blown away,” said Johnson, the field director. “We had an amazing team, an amazing candidate. There’s not one point that I was like, ‘Oh, this is going wrong.’”

After a late night on Tuesday, staff arrived Wednesday morning at campaign headquarters in Roxbury for a team meeting. They cleaned the office and got back to work: a policy proposal about economic development, an early look at the precinct-level results. Kraft spoke with members of the team, and at one point went into a conference room, presumably to discuss the road ahead with senior advisers, Berlin recalled.

“‘Let’s put our head down, get to work and continue chugging,’” was how Berlin described the mood.

Others were less optimistic. Two people involved in the campaign said the mood had grown increasingly grim by Thursday, as staff waited for direction. One person involved in the campaign, who requested anonymity because they were not authorized to speak publicly, said “most staff were in the dark” that Kraft intended to drop out, while those who knew were told “to keep it to themselves.”

Kraft had already scheduled campaign events for later that week. On Thursday at 7 p.m., he was slated to speak at a community meeting in the North End. Instead, he spent much of that day sharing bad news.

Just before 7 p.m. Thursday, he told his team on a conference call that he planned to end his candidacy. He called Wu to tell her directly. Then the announcement went live on WCVB.

“It has never been about Josh Kraft or Michelle Wu,” Kraft wrote to supporters that night. “This campaign has always been about the future of Boston.”

Shirley Leung of the Globe staff contributed to this report.

Emma Platoff can be reached at emma.platoff@globe.com. Follow her @emmaplatoff. Niki Griswold can be reached at niki.griswold@globe.com. Follow her @nikigriswold.