Jen O'Malley Dillon is a star Democratic operative. Can she save Beto O'Rourke's candidacy?
Political strategist and former Obama operative Jen O'Malley Dillon is Beto O'Rourke's campaign manager. Social media

O'Malley Dillon is building a conventional campaign around an unconventional candidate, and some Democrats say she's O'Rourke's best hope.

It was the worst night yet of a dreadful season for Beto O'Rourke.

An hour before, the former Texas congressman from El Paso cratered mightily in front of 15 million television viewers in his first presidential debate. The nosedive came at the hand of his fellow Texan, Julián Castro, who laced into him with an accusation of not having done his homework on policy.

The Texan-on-Texan verbal slashing was Topic A in the postdebate spin room that teemed with the country's most influential reporters and most powerful Democratic power brokers. O’Rourke would eventually enter the lion's den. But before he did, a blonde, bespectacled woman in a distinctive blue dress emerged to make his case for him.

Her presence alone under the "O'Rourke" placard was a clear message to the room of political insiders: No matter how rough the last few months have been for O’Rourke, here, in front of the television cameras, he had the confidence of the most sought-after Democratic campaign manager in the country.

The hiring of this woman, Jen O’Malley Dillon, is the one thing that’s unquestionably gone his way since his campaign launch in March. Nearly every other presidential candidate courted her. But she has chosen to move her husband, twin daughters and 15-month-old son two time zones to the west, from suburban Maryland to El Paso.

"I believe in Beto because he represents a new generation of leadership we desperately need," she said in her only statement for this article. "Now more than ever, we need a new kind of politics that goes everywhere and writes no one off.

"Beto’s determination and ability to connect with people on the ground is unmatched, and that’s what it’ll take to assemble a coalition of voters, many who feel left behind by our current political system, to show up. That’s how we beat Donald Trump and move this country forward."

A veteran of Barack Obama’s two presidential campaigns, O'Malley Dillon is building a conventional Democratic presidential campaign around a most unconventional candidate. Given how rough of a go it’s been, if O’Rourke has a chance at a turnaround, many Democrats say she’s his best shot.

“She is one of the best political operatives of my generation,” said C.R. Wooters, a longtime Democratic hand who is now a lobbyist. “She is an organizer at heart, brilliant and unflappable. She’s also a stone-cold killer when necessary.”

Right now, her candidate is mired at the top of the bottom tier, polling in the low single digits in all of the early states. But even when people privately are ready to declare O'Rourke's campaign dead on arrival, there is a hesitation. Those who know O'Malley Dillon's track record wonder: Can she save him?

Many Democratic observers, nearly two dozen of whom participated in this story, say there is one path to a comeback: O'Rourke must use his charisma to create breakout moment — maybe in a debate or viral video. Then O'Malley Dillon can leverage that attention with the national campaign infrastructure she is building out for him back in El Paso.

Early buzz

Long before an O’Rourke presidential candidacy was a serious consideration, O’Malley Dillon was at the center of Democratic buzz. While voters' curiosity focused on the question of who would run for president, insiders wondered which candidate would land the Obama veteran as a campaign manager — so much so that the president of the Democratic women's group EMILY’s List, Stephanie Schriock, singled her out last fall as the most likely female strategist to break the stranglehold men have on the party’s consultant class.

O'Rourke, meanwhile, had his own buzz. His long-shot bid to unseat Republican U.S. Sen. Ted Cruz, had caught fire in 2018, drawing massive crowds at rallies and adoring profiles from national publications. Even though he lost, the margin of 2.6 points was the closest a Democrat has come to winning statewide office in decades, setting up his presidential run.

His political courtship of O’Malley Dillon over the winter and spring was relentless — he persistently phoned her, and the pair had lengthy conversations about campaign philosophy.

The whole thing came about with a bit of luck. O’Malley Dillon’s business partner and fellow Obama alumna, Stephanie Cutter, was scheduled to appear on a South by Southwest panel in March and canceled at the last minute. O’Malley Dillon stepped in her place and traveled to Austin instead.

O’Rourke pounced.

The candidate and strategist met together over breakfast, along with their spouses. Both sides walked away high on each other.

And there was another intermediary involved in the match: O'Malley Dillon's former employer, Obama.

Obama has been in touch with O'Rourke, as he has been with other Democratic candidates. In December, The Washington Post reported the former president met with O'Rourke not long after the Senate campaign ended. Multiple sources tell the Tribune that the former president recommended O'Malley Dillon to O'Rourke. But just as tellingly, O'Malley Dillon received word that the former president thought she should take the job, according to two people with knowledge of the communication. A spokesman for Obama declined to comment.

The deal was sealed by the end of March.

"Do whatever she tells you"

O'Rourke's Senate campaign comprised mostly longtime friends from El Paso. Big-name polling and television political consultants tried in vain to pitch the candidate, but for the most part he avoided any person who carried even a trace of national politics.

That free-wheeling, volunteer-driven kind of campaign worked well in a world where O'Rourke essentially clinched the Democratic nomination before he launched and where he was running against Cruz, an incumbent who could organically motivate progressives and moderates in O'Rourke's favor.

O'Rourke clearly made the calculation that such a model would not scale in a national campaign, and most national Democrats agreed with him. For one thing, it's implausible to drive off to New Hampshire or Iowa in a minivan. But also, the Democratic nomination is not measured in the popular vote — it's won by delegates. Delegates are won in two ways: relationships within the party and motivating people to turn out to often obscure caucuses and primary contests.

In campaign speak, this is known as “field,” and it’s O’Malley Dillon’s expertise. Typically the grunt work of field organizing is the entry path for most aspiring political operatives, and they promptly look for an escape to other jobs as quickly as possible.

But O’Malley Dillon built her career on it. She started early, with then-Vice President Al Gore’s 1999 New Hampshire campaign, not long after she graduated from college. Even then, friends recall a tough, direct operative who is impatient with interpersonal drama and who can push her staff like a drill sergeant.

It’s a drive rooted in sports. She played first base and was a co-captain on the Tufts University softball team in her native Massachusetts.

Over the next 20 years, she worked on a series of banner campaigns — presidential and Senate races — that are still discussed to this day.

O’Malley Dillon once helped eke out a 524-vote Democratic Senate victory in South Dakota. And before moving to the Obama camp, she was key to former U.S. Sen. John Edwards’ two second-place finishes in the 2004 and 2008 Iowa caucuses. While she started the 2008 cycle as the Iowa state director for Edwards, she eventually made her way to the Obama campaign and was his deputy campaign manager for the 2012 campaign.

She earned legendary status within Democratic circles in November 2012 when she was Obama’s deputy campaign manager in charge of field and data. That campaign pioneered analytics and turnout models and outperformed the late polls.

She gave birth to twins a week after the election.

"The work that she does while also being a young mom, having these kids, being a supportive friend and colleague, I just find it really impressive," said Christina Reynolds, a top staffer at EMILY's List who has worked often with O'Malley Dillon. "People talk about work-life balance; I wish I could get as much done in a week as she she's done by lunch."

But O'Malley Dillon has also suffered setbacks. Edwards may have done well in Iowa in 2008, but his was a campaign plagued with the candidate's personal scandals. And O’Malley Dillon was the top staffer at the Democratic National Committee in the roughest Democratic year in recent memory, 2010.

"Jen is the best player in the game because she thinks in three dimensions: how best to message, organize and use technology,” said Jennifer Palmieri, who worked with O’Malley Dillon on three presidential campaigns. “It’s never the same strategy each campaign, but she is always churning on how the game can be played better.”

Democrats point to a number of qualities and approaches that set her apart.

For one, she is one of the few operatives who is an expert in both New Hampshire and Iowa. And thanks to her general election experience with Obama, she has run field operations in the usual battleground states.

In that vein, in the telling of her former colleagues, O’Malley Dillon tackles each state as a different campaign. Her approach to persuasion, mobilization and voter registration differs from place to place.

And with all of these campaign experiences, she has the esteem of consultants, staffers and party officials that she can leverage on behalf of O'Rourke, who was mostly a maverick during his time in the U.S. House.

“One of the things is, I’ve been doing politics a long time,” said Cutter, her 2012 Obama reelection colleague. “You learn who you can trust and who you can’t. I would trust my life with Jen O’Malley.”

But so far, O'Malley Dillon has struggled to help O'Rourke's campaign get off the ground. His fundraising in the second quarter had a marked drop-off, and he is no longer in the top tier of polling within the Democratic field. Even so, the campaign continues to be a magnet for talented up-and-coming staffers, and his on-the-ground infrastructure continues to expand. Earlier this month, his campaign opened 11 field offices in Iowa.

Wooters, who has known O'Malley Dillon since they worked together on the Gore 2000 campaign, said he has noticed how young Democrats are overwhelmed with presidential campaign job offers, given the sheer volume of candidates.

“Sometimes I get asked for career advice from young organizers," he said. "If the conversation turns to the Beto campaign, I immediately tell them that working for Beto means working with Jen, and that is not an opportunity they should pass up. It's usually followed up with something like, ‘Do whatever she tells you.’”

The thrill is gone

But not everyone is thrilled with her influence.

When discussing the O'Malley Dillon hire, and the broader O'Rourke presidential campaign, some Democratic activists characterize these staffing and strategic changes in a manner akin to an indie rock groupie’s despair that a favorite band has signed on with a major record label and is now producing watered-down, uninspiring music to the masses.

“Exactly, and all of the soundtracks start sounding the same,” laughed Lillian Salerno, a podcast host and former Texas congressional candidate. “Everything sounds like Kanye.

“I think Beto’s campaign lost a lot of its heart in the way it’s transitioned,” she added.

Soon after the O’Malley Dillon hiring, The Intercept began publishing a series of articles taking note of corporate ties with O'Rourke campaign hires. The issue for some progressives is O’Malley Dillon’s work in the consultant firm she founded, Precision Strategies. While the firm is involved in campaigns, its clients also include corporations.

And not long after O'Malley Dillon signed on, two of O’Rourke’s top Senate race field staffers — Becky Bond and Zack Malitz, 2016 veterans of the Bernie Sanders presidential campaign — left O'Rourke's presidential campaign. Whether or not it was intentional, some progressives interpreted that exit as a signal that it was worth giving other Democratic candidates consideration, a situation that did not exist when O’Rourke faced only minimal intraparty opposition in his Senate race.

But these differences are possibly as much about philosophical differences on strategy.

The O'Malley Dillon school of campaigns — and that of essentially every other Democratic presidential campaign — involves a massive field staff infrastructure that engages with volunteers. In the 2018 Senate campaign, the O’Rourke team's structure had fewer staffers who managed super-volunteers and gave those foot soldiers unique, direct ownership of their local organization.

“Jen runs a very tight ship, almost a disciplinarian ship when it comes to field,” said an operative who worked with her in the past but who declined to speak on the record because of personal sensitivities within the party. “People who are used to running a very organic, bottom-up, no-rules field operation would have a culture clash with that.”

And it is a reasonable question to ask: While it may take the kind of operation O'Malley Dillon knows how to build to win a nationwide campaign, can a free-spirited candidate like O'Rourke thrive amid a traditional operation?

"Can we get your name?"

But even as O’Malley Dillon is well-known among professional Democrats, she is one of the least known former Obama operatives within political pop culture.

During the Obama years, young staffers eagerly lined up to fashion themselves as real-life "West Wing" characters for magazine profiles and future business opportunities. In that same window of time, O’Malley Dillon mostly avoided the spotlight. The O'Rourke campaign declined to make her available for an interview for this article, opting instead to send a statement through a spokesperson.

"She's ultimately one of the behind-the-scenes players — and likes it that way," said Palmieri. "But ask any one of the more famous names associated with Obama, and all of them would point to Jen as being key to his success.

"President Obama included," she added.

When O’Rourke fumbled at last month’s Miami debate, O'Malley Dillon's moment in the spotlight was utilitarian. The more seasoned reporters and operatives understood the message she was sending with her spin room appearance: She was extending her professional credibility and faith to her struggling candidate.

After spinning O'Rourke's performance, she stopped to catch a breath, and a young reporter in the scrum asked her one of the baseline rules of journalism.

“Can we get your name?”

The surrounding reporters cringed. People of O'Malley Dillon's stature just don't get asked that question.

“Jen O’Malley Dillon, the campaign manager.”

“Can you spell it?”

“The whole thing?” asked O'Malley Dillon.

“Yes. For accuracy.”

It served as a reminder: For all of her credibility, the consensus among Democrats is that all an operative — even one of O'Malley Dillon's caliber — can do is help a candidate. She cannot save him.

The whole predicate on this pairing is based on O'Rourke surviving the early state's caucuses and primaries in February. If he can place in the top three positions in New Hampshire or Iowa, O'Malley Dillon can implement what is expected to be a daunting national machine to vacuum up delegates.

Is it possible?

“If there’s anybody who can do it, it’s her,” said Cutter, her business partner.

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