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For Obama team, a Mass. touch

Campaign deputy honed skills early

By Matt Viser
Globe Staff / April 25, 2011

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WASHINGTON — For the 10-year-old, the conversation with her father had turned uncommonly serious, even if the topic, politics, was a family staple.

“If you leave the Democratic Party,’’ he told her, “you will be leaving your people.’’

Nearly a quarter-century later, Jennifer O’Malley Dillon is still with her people.

O’Malley Dillon — who grew up in Franklin, Mass., played first base on the softball team at Tufts University, and took her first campaign job working on Scott Harshbarger’s bid to become Massachusetts governor in 1998 — is now deputy campaign manager in President Obama’s reelection campaign.

Since moving earlier this month to Chicago, where Obama’s campaign headquarters is based, she has been poring over maps and data from the shellacking that Democrats took in the 2010 midterm elections. It is part of an extensive effort to figure out what went wrong and recalibrate the party’s strategy.

The analysis could lead the campaign to some surprising conclusions: placing more emphasis, for example, on North Carolina, a one-time GOP stronghold, than Ohio, traditionally a key battleground state. Ohio is trending older and has a relatively stagnant economy, while North Carolina has a younger and more diverse population that could be more attuned to Obama’s message and appeal.

“It’s not an accident that we are holding the convention in Charlotte,’’ she said during an interview at the Democratic National Committee headquarters.

O’Malley Dillon is in a unique position to apply the lessons from the Democrats’ debacle last year: She has spent the past two years as executive director of the Democratic National Committee.

That period featured a major legislative victory — health care overhaul — and a huge political price paid for its passage. In addition to the midterm pasting, when Republicans took over the House and cut into the Democrats’ hold in the Senate, Obama’s polling numbers tumbled.

Democrats struggled against the rush of antigovernment fervor and outside money and could not find a consistent message that resonated with voters.

“We certainly could have done a number of things better,’’ conceded O’Malley Dillon, who oversaw day-to-day operations of the organization and helped craft the 2010 strategy.

One hurdle, she said, was translating the excitement over Obama’s 2008 victory into commitment for his agenda.

Democratic candidates also did not effectively use social networking to attract voters, she said, and did not do enough grass-roots organizing.

She is still analyzing what went wrong in some of the states: why Democrats lost soundly in Ohio, for example, but saw success in such key states as Colorado and Nevada. She and other Democrats are using the 2010 losses as a motivational tool.

“There won’t be a situation where we’re going to be riding this momentum and energy, and we know that — and the president knows that, too,’’ O’Malley Dillon said. “So we need to figure out how to better communicate, and do it in ways that young people, or people affected by the economy, or older people feel like we’re communicating directly with them.’’

O’Malley Dillon’s household oozed politics. Before the family moved to Franklin, Mayor Kevin White would visit their house in Jamaica Plain for neighborhood meetings. In elementary school, she met Governor Michael Dukakis, and several years later she stayed up late to watch his nomination acceptance speech at the Democratic convention in 1988. Her cousin, Matt O’Malley, is a Boston city councilor from Jamaica Plain.

“I count myself as an adviser to the president,’’ said her father, Kevin O’Malley, a former Ayer schools superintendent. “I don’t think my daughter delivers my messages to the president, but I am not shy about telling him what he should do or not do.’’

After graduating from Tufts University, O’Malley Dillon got her start answering a 27-line phone for Harshbarger’s campaign. “Once you can manage a telephone,’’ she said, “you can really manage everything.’’

Charles Baker, a longtime Boston-based Democratic operative, described O’Malley Dillon’s debut. “You saw this woman who at 20 or 21 [was] just making that room hum. You could just tell she was incredibly effective and no-nonsense at getting stuff done,’’ said Baker.

She also represents a new generation of Massachusetts-bred national operatives who did not predominantly come from the worlds of Edward M. Kennedy, John F. Kerry, or Dukakis.

O’Malley Dillon is described by those close to her as a plain-spoken, detail-oriented worker. She is a fan of “The Sound of Music,’’ a reader of People magazine and Women’s Health, a lover of Jane Austen’s “Pride and Prejudice,’’ and an owner of a shoe collection many would covet.

At 34, O’Malley Dillon is already a veteran of presidential campaigns, working for Al Gore’s New Hampshire office in 2000 and for John Edwards in 2004 and early 2008 before joining Obama’s team. In the general election against Republican nominee John McCain, she directed operations in 22 states, including Ohio, Pennsylvania, and Florida. Obama carried all three of those battleground states, as well as several that had traditionally leaned toward Republicans.

“She had an incredibly important role,’’ said Mitch Stewart, who was the Virginia state director and has run Organizing for America, a DNC-affiliated group that aimed to keep Obama’s campaign network mobilized. “The fact that we won Indiana, North Carolina, Virginia — she is as responsible as anyone on the campaign for making that happen.’’

Politics remains a family affair. She met her husband, Patrick Dillon, while working on the Edwards campaign. They fell for each other while getting left behind by their friends at the Iowa State Fair; it’s “about as cheesy as it gets,’’ O’Malley Dillon said.

They became engaged while she was managing a governor’s race in Florida and he a governor’s race in Iowa. Her candidate lost; his won. So they moved to Iowa. Her husband recently left his post as deputy White House political director to join Hilltop Public Solutions, a Washington-based consulting firm.

O’Malley Dillon now must help steer a campaign that has several challenges.

Her role will focus on individual states, trying to determine which areas provide the most fertile ground. . She’ll operate largely behind the scenes, going over maps, analyzing voter rolls, and talking with volunteers.

“You’re not going to see me on the speaking circuit very often,’’ she said.

In the 2008 election, Obama was able to ride a wave of excitement over his appeal and over a captivating Democratic primary. This time, he will have the powers of the presidency, but Republicans will have a nominating contest that will dominate headlines for months.

“If we try to recreate 2008, we’re going to lose,’’ she said. “So we have to have something new and give people a reason to participate and participate early.’’

The challenge is exacerbated, she said, because some of the building blocks of 2008 no longer exist in states where Democrats saw big losses two years later. Key surrogates such as Pennsylvania Governor Ed Rendell are no longer in office and have been replaced by Republicans.

“I mean, Ohio’s infrastructure’s gone, Pennsylvania’s infrastructure’s gone,’’ O’Malley Dillon said. “Florida is a behemoth of a state with very limited infrastructure. . . . Just organizing in a state like Florida cost us $60 million in 2008.

“There’s lots of those things that keep me up at night, but also excite me,’’ she said. “I think we have a number of different pathways to get to victory. I’d even say more than the Republicans.’’

Matt Viser can be reached at maviser@globe.com.