Throughout the presidential campaign, Jennifer O’Malley Dillon often repeated a mantra from her collegiate softball days to rally staff on endless Zoom calls: We can do hard things.
Even for someone with an optimistic attitude, 2020 presented a particularly high number of “hard things” for the woman running Joe Biden’s campaign — a pandemic that turned traditional campaigning upside down, a polarized left that wasn’t thrilled about a three-time, middle-of-the-road presidential candidate, an unpredictable opponent who frequently said the election was rigged before any votes were cast.
But the mantra, however unflashy, turned out to be true.
“Once she commits to a goal, she’s going to grind it out,” said longtime friend Cloe Axelson, who played softball at Tufts with Dillon and worked on early campaigns with her. “She’s so tough, and she just does the work.”
Dillon, 44, is the second woman ever to run a winning presidential campaign, and the first to achieve victory for a Democratic candidate. (Kellyanne Conway was the first overall, steering President Trump’s campaign for three months in 2016). A veteran operative who had helped run both Barack Obama campaigns, she was widely courted in the Democratic primary, and led Beto O’Rourke’s campaign before taking over Biden’s in the spring.
“She’s the best in the business,” said Mitch Stewart, who served as battleground states director for Obama’s 2012 reelection, in an e-mail. “She’s super smart, thorough (every detail is thought through) and disciplined.”
Relatives and colleagues describe her as a strategic thinker whose fundamental values were shaped growing up in an Irish Catholic family in Jamaica Plain and Franklin.
After decades in politics, Dillon faced a previously unimaginable presidential campaign this year. When the coronavirus closed campaign headquarters in March, not long after she came on board, she decamped to the attic of her home in the D.C. suburbs. From there, she transformed the flailing Biden campaign into a well-resourced juggernaut capable of defeating an incumbent president — while her children, 8-year-old twin girls and a 3-year-old boy, went about their days downstairs.
As the head of the campaign, Dillon expanded the Biden operation tenfold and spoke with the former vice president at least every day.
Dillon’s under-the-radar style stands in sharp contrast to the cable news profiles many top campaign operatives have cut in recent years, with people like Karl Rove, Robby Mook, and Conway becoming household names (at least to those watching lots of cable news). By contrast, some of Dillon’s peers publicly fumed when The New York Times failed to mention her once in its 4,000-word post-mortem of how Biden won the presidency.
“She’s one of the most experienced people out there who most people have never heard of,” said Addisu Demissie, Cory Booker’s presidential campaign manager. “She knows how to run things.”
As a lifelong Democratic operative, Dillon was an appealing choice for the moderate, institutionally loyal Biden. She’d been deputy campaign manager for Obama’s 2012 reelection. She’d done a stint as the executive director of the Democratic National Committee, and cofounded a public relations firm, Precision Strategies. (The Biden campaign did not make her available for an interview.) Her first paid political job was working on Scott Harshbarger’s gubernatorial bid in 1998.
“‘We have a really comfortable life . . . It would be easy to sit this out,’” Dillon’s husband, Patrick Dillon, recalled her saying ahead of the 2020 race in an interview with the Globe. But ultimately, she couldn’t do it.
She told her husband, “ ‘I need to go do whatever I can to beat Donald Trump, and I need to be able to look our kids in the eye and say that we did that,’ ” recalled Patrick, whom she met when they both worked on John Edwards’s 2004 presidential campaign in Iowa.
Dillon’s father, Kevin O’Malley, was undergoing chemotherapy and radiation in the spring, he said in an interview, and Biden was particularly attuned to what the family might be going through. Biden’s sonBeau died of brain cancer in 2015.
"He asked Jen [how I was doing], evidently more than once,” said Kevin O’Malley, who has finished his first round of treatment.
Dillon grew up the second of four kids in a spirited political family. Her mother, Kathleen O’Malley, was an elementary school teacher and her father was a public school principal and superintendent, as well as the president of their neighborhood association in Jamaica Plain. Mayor Kevin White attended meetings at their home before they moved out of the city.
“Our grandparents always instilled in us the Boston Democratic impulse: Trying hard, working hard, and helping your neighbors," said Matt O’Malley, Dillon’s cousin and a Boston city councilor in Jamaica Plain.
Fiercely competitive, Dillon played three sports at Franklin High, and was cocaptain of the Tufts softball team her senior year. In addition to developing a “bullet for an arm,” as a teammate described her, she also learned how to build a team, a skill that would be essential on the national stage.
“She made sure that every person on that team felt important, whether you were on the bench or whether you were a starter," said Axelson. (Dillon was quite the motivator: Axelson said she “skipped the entire January of my senior year to sleep on Jen’s floor and be her intern” on the Gore campaign.)
As a field organizer in that campaign, Dillon worked closely with unpaid volunteers, recruiting door knockers and phone bankers, and making them feel that their contribution mattered, colleagues said.
As she rose in the political world, Dillon considered how to raise children while devoting herself to a demanding career. Early on, her husband recalled, Dillon had coffee with someone who advised her that if she wanted to run a presidential campaign someday, it might be better to forgo having kids.
But Dillon chose to have children during the 2012 Obama campaign — she gave birth to the twins a week after Election Day.
“Obama came in the day after he was elected in 2012, and he said, ‘I thought you were going to the hospital,’ " recalled Kathleen O’Malley. "She said, ‘I was, but my blood pressure dropped when you won!’ So she was able to put it off for a week.”
Dillon is a fan of Jane Austen novels and dances with her kids to the The Chicks during breaks, O’Malley said. Many nights during the campaign, she would return calls at 11 p.m. from her Peloton bike in the basement, “which is, to be clear, insane," her husband said.
In the brutal world of political campaigns, other working mothers saw Dillon as a role model.
“What I particularly value about her is that she doesn’t pretend it’s easy," said Julie McClain Downey, who served as director of state communications for Booker’s presidential campaign, and gave birth during the primary campaign.
A campaign running from our house in the age of covid is all kinds of weird most days, but one lucky break in it all was getting to watch my son help mama @jomalleydillon quarterback a history-making (and leakproof) veep rollout during afternoon snack pic.twitter.com/0k13D0wpkO— Patrick Dillon (@mpdillon) August 12, 2020
The kids were with Dillon’s parents in Franklin for the final two weeks of the campaign, and called her “yelling and screaming and jumping up and down" when Biden won, Kathleen O’Malley said. Dillon is planning to join them in Massachusetts this weekend to celebrate the victory, although she has also been charged with keeping an eye on the Georgia recount, according to Politico.
As for what’s next, political observers and friends said Dillon is weighing her options — but that you can expect to see her name again soon.
“She’s obviously one of the most important political operatives in America today,” said Charles Baker, a longtime Boston-based Democratic operative who first met Dillon in 1998. "If not the most.”