Jane Swift and Me, 20 Years Later

It’s been two decades since the former governor booted me off her front porch as a young reporter. What I’ve learned about her—and myself—since then.

Portrait of former Massachusetts Governor Jane Swift in 2022

Former Massachusetts Governor Jane Swift today. / Photo by Ken Richardson

On a warm, sunny day this past summer, I drove up a long driveway to former Governor Jane Swift’s Williamstown farm, located high on a verdant hilltop with postcard views of the valley below. She welcomed me into her home, apologized for the clutter, and offered me a seat at her kitchen table. “Have you ever come out here before?” she asked me.

I had. It was the spring of 2001, Massachusetts Governor Paul Cellucci had been named ambassador to Canada, and Lieutenant Governor Swift—pregnant at the time with twins and with a toddler at home—had just been elevated to governor.

As lieutenant governor, she’d had an embattled (to say the least) relationship with the press. I was a twentysomething Boston Globe reporter whose editor had suggested—well, it wasn’t really a suggestion—that I knock on Swift’s door and ask for an interview. Today, Swift doesn’t remember much about that night, but I vividly recall her appearing in a bathrobe, enormously pregnant, extremely unhappy to see me, and chewing me out for violating her privacy.

When I refreshed Swift’s memory about what happened next—I drove back down the hill past police cars with flashing lights that had clearly been summoned to barricade the driveway lest another poor reporter wander up—she burst out laughing. “Sorry,” she said with a shrug.

Meanwhile, I was the one who wanted to apologize. In fact, that was precisely why I had invited myself over to Swift’s home in the first place: not to reminisce about that night in Williamstown—I was just doing my job— but to repair one particular moment from that stretch of torturous media coverage of Swift between 1998 and 2002.

I’ve long wanted to reexamine what happened in those years when the press leaped onto this novelty story of a young mother with small children navigating a massive public role. Every detail of her parenting choices was controversial: the fact that her husband was the primary caregiver; the times when she brought her toddler to the office; the taxpayer-funded helicopter ride she took from Boston to western Massachusetts when her daughter had pneumonia; the meetings she ran through a speakerphone while on bed rest during her pregnancy. When Swift was in labor, Secretary of State William Galvin—citing the sanctity of the state constitution—proposed that the Governor’s Council descend on Swift’s hospital room, where she was having contractions six to eight minutes apart. There were other absurdities, not to mention two-newspaper-town exuberances and ill-advised PR moves that all contributed to a maelstrom of negativity.

Here’s what I regret: At some point in the middle of that swirl, I was a panelist on political analyst Jon Keller’s year-in-review show on the long-since-shuttered WB56, and Keller asked me if I had any sympathy for Jane Swift. And I said, “No.”

Honestly? None? In a few short years, I would have kids of my own and conduct the less-visible version of that tap-dancing act, the one that happens when you’re not rich enough to outsource childcare, and also, you want to spend time with your kids, and also, you know you can be good at your job. I would arrive at the conclusion that every working parent is trying to hold it together, and everybody’s largely on their own to figure out how, even someone who is nominally the most powerful person in the state.

The novelty of a young mother to small children navigating a massive public role thrust every detail of Jane Swift’s parenting choices into a harsh media spotlight. / Photo by the Boston Globe via Getty Images

If I didn’t realize that at the time—well, I was kind of a little shit, right? “I’m sorry,” I told Swift at her kitchen table. “I feel really bad about that.” She laughed, a little ruefully this time, looked me in the eye in acknowledgment, and said, “Yeah.”

Then, for a couple of hours, we picked over what happened two decades earlier and what came next as she raised three girls who are now in their twenties, moved from Williamstown to Vermont and back again, and built a successful second career in education policy—trying, through it all, to give working mothers the support she never fully received. “I promised myself that there would come a time,” Swift told me, “that when I wasn’t in the spotlight and could speak up, that I would.”

And she has, both explicitly (establishing family leave and flexible-work policies in the companies she’s led) and implicitly (leading by example if she needs to leave work early for a family event). If Swift was once a public symbol of the challenges of managing motherhood and a career, she’s now a semiprivate example of how you can actually make it happen when nobody’s scrutinizing your every move.

Swift is also a symbol of what might have been if we’d all had a little more perspective, a little more generosity, and a little more restraint. It’s been nearly 21 years since Swift dropped out of the 2002 race for governor, ceding the Republican nomination to Mitt Romney, a father of five with a stay-at-home wife, a political pedigree, and a private equity fortune. It has taken that long for another woman of any age or parenthood status to become governor of Massachusetts. Maura Healey has faced her own share of obstacles and earned her own share of firsts. But one thing she didn’t have to balance was parenthood and politics. If she had, would she have had an easier time than Swift?

Swift answers questions at the 2008 Republican National Convention in St. Paul, Minnesota. / Photo by Max Whittaker/Getty Images

One of the things Swift marvels about, looking back, is her expectation that it would be easy. But then, she was part of what she calls the “Title IX Generation,” the first women to emerge from college with mandated equality in sports and a belief that women’s parity would continue beyond school—that they could accomplish anything.

As a sophomore at Trinity College, Swift interned for her home district state senator, Peter Webber, and discovered that by dropping Webber’s name to some state college bureaucrats, she could help an acquaintance who had lost a scholarship due to an administrative glitch. “Literally, it was the difference between whether or not this young woman was going to be able to go back to school,” Swift said, and “the power of that” convinced her to enter politics. There was more that she wanted to fix. Armed with a chip on her shoulder over the struggles of working-class towns and experience watching her dad, North Adams’s most prominent plumber, work behind the scenes on political races, Swift worked in Webber’s office after graduation. When he retired, she ran for his seat and won. She was 25.

Things went that way for years as she traveled the charmed path of a rising political star. Swift was 31 when she ran for U.S. Congress; she lost but earned stature in Massachusetts’ Republican party and a string of high-profile appointed government jobs. She was 33 when Cellucci chose her as his running mate—just as she was also about to learn that she was pregnant.

Progress, right? But the barrage of national attention, celebrating one of the first politicians in the nation to run for statewide office while pregnant, also put a microscope on the most personal aspects of a new parent’s life. Strangers debated Swift’s childcare plans. Radio hosts questioned whether she could concentrate on her job. The head of the Christian Coalition of Massachusetts essentially declared, to anyone who would listen, that Swift should stay home with her baby. It goes without saying, but I will say it for the 85,627th time: Men running for office do not, as a rule, get asked how they will manage young children while doing the public’s work.

Still, once Swift was in office, she felt an obligation to prove her worth, in part by doing whatever Cellucci’s staff asked her to do: all of the after-hours ceremonial tasks, including an event at Logan Airport on the night of her ill-fated helicopter ride. “I was so worried that showing any sign of weakness—or that I was, in any way, not doing the job exactly right—would look bad for every woman who was trying to do this,” she told me. “The biggest mistake is, I should have told them all to go pound sand. The biggest thing I regret is all the times I showed up to work when I should have just said, ‘I need to go deal with family.’” But she had scant support or examples to follow in the State House, which was practically devoid of women in power, let alone working mothers. “She was deposited in a position that she might not have been completely ready for at a difficult time in her life, amid one of the most sexist political cultures in the country,” Jon Keller told me when I called him to compare memories. “It was an impossible spot.”

Here’s where I tell you about the moment when Keller officially became one of my favorite people in Boston media. It was July 2004, and we were both at the then–Ritz-Carlton, covering the dedication of the Public Garden’s 9/11 Memorial. I was nine months pregnant, and Keller was the only person in the room who thought to grab me a chair. Eventually, I’d recognize that day as a metaphor for navigating working parenthood. You rely on help where you can get it. You slip out of work, hoping nobody will notice, and white-knuckle your way through traffic so you can get your kids before the daycare starts charging a dollar a minute for late pickup. You panic if the school system calls a half-day on a Wednesday, and you have to find childcare. And you try your damnedest to do your job well through it all.

Swift leaving Brigham and Women’s Hospital with her new babies, Lauren Alma and Sarah Jane, in 2001. / Photo by Tom Landers/The Boston Globe via Getty Images

In other words, Swift’s struggles were universal, but they were never framed that way. It wasn’t: Wow, the system is so stacked against working mothers that even the lieutenant governor is having trouble. Instead, it was: This woman with a prominent job and a decent salary and a stay-at-home husband is getting perks that most of us don’t have.

What stung most, Swift told me, were the “bruuuutal” stories that appeared the day after some scandal broke over something she did or didn’t do. (This all happened pre-Twitter, so we spoke in ancient media terminology: “second-day stories” and “man on the street.”) “I don’t know if you ever did the Gymboree interviews with the stay-at-home moms?” she asked me, describing a standard story in which a reporter would descend on a “Mommy and Me”–type class and ask—in Swift’s words—“What does Jane Swift’s failure mean for every woman who’s ever going to have a baby and try to work?”

I did write a form of that story once, in 2002, interviewing young women I found around Beacon Hill on the day Swift, by now the governor, announced she wouldn’t run for a new full term, declaring at her press conference that “something had to give.” One 22-year-old in a bagel shop told me that Swift’s challenges made her wonder whether she wanted kids at all.

Through those years, PR consultants and State House staff were advising Swift to avoid engaging in a full-throated self-defense—or, really, talking about her family life at all. The thinking, she says, was that if she said anything about her kids, she’d be accused of using them as props or challenging anyone who’d made a different decision about childcare. “It felt like every choice I made, there was no way to defend it. You were either a bad mother or a bad governor,” she told me. “But the less I answered, the more I became a caricature of somebody I didn’t really recognize.”

Today, the Barbara Lee Family Foundation, which supports women in politics, advises candidates to acknowledge their own childcare choices, then quickly pivot to policy. “We recommend people say something like, ‘What works for me doesn’t necessarily work for everyone else. I’m lucky that my parents live nearby, and they can pitch in and help with the kids, but not everyone has that option, so that’s why we need all-day kindergarten,’” executive director Amanda Hunter told me.

Swift tried that approach herself, it turns out, early in the media fascination with her. In a New York Times article from 1998—the headline was “A Pregnant Candidate Discovers She’s an Issue”—Swift declared that “if we’re going to focus on the pregnancy, I wish we could shift the debate to ‘What, then, do Jane Swift and Paul Cellucci think they can do on daycare and creating more opportunities for flextime and meaningful part-time work?’”

When I read that quote back to Swift more than 24 years later, she wryly noted that she had an answer. As lieutenant governor, already battle-scarred, she worked to create the first-ever maternity- and paternity-leave policy for state employees. She and her team researched best practices, found a solution that wasn’t costly, and faced no resistance on Beacon Hill. No one thought it was a bad idea. It hadn’t been done before because it just, well, hadn’t come up. “Often, these issues go unaddressed because there’s no one in a position of power who has had to deal with it, and then who thinks to ask the question,” Swift told me, calling the policy “one of the small, quiet things we did.” To a working parent, parental leave where none existed is hardly a small benefit. But Swift didn’t want to publicize the work at the time. She knew how every story would go, and she didn’t want the spotlight back on her family.

Jane Swift and some awesome rescue goats

Swift at home with her rescue animals, on the Williamstown farm she’s converted into an education center. / Photo by Suzanne Kreiter/The Boston Globe via Getty Images

Swift is now two decades into her second act: a career in education, building on the policy work she’d done since her days in the Massachusetts Senate. She’s served on the boards of education nonprofits and venture capital firms. She ran Middlebury Interactive Languages, a company that creates digital world-language curricula, and LearnLaunch, a nonprofit that convenes and trains education-sector leaders. She raised her kids out of the media’s glare. She launched a Twitter feed that showcases her dry sense of humor; these days, it’s heavy on content about football and rescue goats. (In addition to her education work, she’s turning the family farm, beloved by her late husband, Chuck Hunt, into a rescue and education center.) She recently started a Substack newsletter she describes as “mixing politics, sports, and grief”—the subjects most familiar to her, now that mourning Hunt, who died late in 2021, has become part of her daily life.

For several years, Swift also taught a course on leadership at Williams College, bringing in speakers from media and politics and picking apart her own story. “There was a lot of—problem solving’s not the right word, but talking about how can things change, and what does that look like,” recalls Annie Gilmore, her former teaching assistant. “And a lot of it is centered around women supporting other women.” Since the class ended, they’ve stayed in touch; Swift recently offered Gilmore advice about going on maternity leave.

Today, Swift is nationally known within education circles for advocating for more women to become principals, superintendents, and state education chiefs. She’s also known as an energetic behind-the-scenes mentor on issues of work and life. “She has this unofficial network of really powerful women in education. They look to Jane and call her and ask her for advice,” says Anna Edwards, cofounder of the educational consulting firm Whiteboard Advisors, who herself reached out to Swift a few years ago when her own husband was hospitalized. “She shared some of the playbook with me of how to be a caretaker, how to keep things stable for the kids, what to watch for to make sure they were okay,” Edwards says. And Swift encouraged her to stay in the game: “[She told me] that the work that I was doing was really important and that I shouldn’t feel bad about trying to make an impact and do that, too.”

Now, Edwards says, she and her business partner want to give the same support to their employees, most of whom are under 32 and on the precipice of building families. They offer remote work options, flexible hours, and a childcare stipend. They also bake family life into company culture: When Edwards’s kids were small, she would leave the office at 4:45 to relieve the nanny, then get back on the computer later at night. “We created an environment where me leaving [during] what was technically the workday to take care of my family was not an issue at all,” she says.

Jamie Candee, CEO of the Minnesota-based education tech company Edmentum, also counts Swift as a mentor and role model. Candee, who had an eight-month-old when she took her first chief executive job, says her company offers paid time for volunteer work, which many of her employees use to help at their kids’ schools. “I talk very openly about what’s going on with my kids and my family,” she says, “and ask them about what’s going on with their families.”

If the private sector is changing—at least, in some rarefied, white-collar corners— politics is still a work in progress. Yes, Illinois Senator Tammy Duckworth was allowed to bring her baby on the U.S. Senate fl oor, and Boston Mayor Michelle Wu can talk about her school-aged children without consequence. But young mothers are still rarities in government: The Vote Mama Foundation which researches mothers in office, found that before the most recent election, women with school-aged children made up only 7 percent of Congress and 5 percent of state legislatures. Since 2019, the organization’s PAC has supported more than 400 candidates—mothers running for everything from school board to U.S. Senate, founder and CEO Liuba Grechen Shirley told me. “Every single one of them,” she said, “has been asked, ‘But who will watch your kids when you campaign?’”

Grechen Shirley’s solution is the same as Swift’s: Get more mothers in office. Make it easier for women who aren’t already wealthy to put in long hours of campaigning. (In 2018, Grechen Shirley successfully petitioned the Federal Election Commission to allow candidates to use campaign funds for childcare.)

Swift has no plans to run again—and no connection to Vote Mama—but she’s involved in that cause. “I do a lot quietly,” she told me. “I write checks. I talk to a lot of candidates.” And she takes comfort in the changes she’s witnessed, in the culture if not the numbers: “I see a lot more women rallying together to help other women, to have other women’s backs, to be supportive. I think that’s more the norm than certainly it was when I was in office.”

I asked Swift if she thought a woman in her circumstances would have an easier time in office today. She paused and thought about it. “I think it would be different,” she finally said, “because I know how my daughters would react—like, if they were your man-on-the-street interview today.” Compared to the young woman in the bagel shop on Beacon Hill in 2002, she thinks, the future they’d imagine isn’t bleak. “They see these women who are successful,” Swift said. “They expect a level of equality that I naively expected. But they actually are able to act together to make sure it becomes the norm.”

“Maybe that’s the difference,” I told her. “You talked about expecting equality. But when you ran into a real-life situation that wasn’t equal, you felt all the pressure—”

“There was no one!” Swift interrupted, laughing a little ruefully again. And then she recalled the advice she got at the time from her mother about what to tell the press when the spotlight was so searing, and the sympathy was nonexistent. “My mom was like, ‘Tell them it’s hard to be first,’” she said. “Which was the best answer I ever got.” She said it again: “That’s a great answer, Mom. ‘It’s hard to be first.’”

Joanna Weiss is Editor-in-Chief of Experience magazine and a contributing writer at POLITICO Magazine, where she covers the intersection of politics and culture. She was a columnist, television critic, and political reporter at the Boston Globe for 16 years.

First published in the print version of the January 2023 issue, with the headline, “Jane Swift and Me.”