Publicly, Clinton insists she’s many months away from a decision. Hillary Clinton's shadow campaign

Early last summer in her Georgian-style home near Washington’s Embassy Row, Hillary Clinton met with a handful of aides for a detailed presentation on preparing for a 2016 presidential campaign.

Three officials from the Democratic consulting firm Dewey Square Group — veteran field organizer Michael Whouley, firm founder Charlie Baker and strategist Jill Alper, whose expertise includes voter attitudes toward women candidates — delivered a dispassionate, numbers-driven assessment. They broke down filing deadlines in certain states, projected how much money Clinton would need to raise and described how field operations have become more sophisticated in the era of Barack Obama.


The meeting was organized by Minyon Moore, a longtime Clinton intimate also at Dewey Square who has informally become the potential candidate’s political eyes and ears of late. Clinton listened closely but said little and made no commitments, according to people familiar with the nearly hourlong gathering. It appears to have been the only formal 2016-related presentation Clinton has been given from anyone outside her immediate circle.

Publicly, Clinton insists she’s many months away from a decision about her political future. But a shadow campaign on her behalf has nevertheless been steadily building for the better part of a year — a quiet, intensifying, improvisational effort to lay the groundwork for another White House bid.

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Some of the activity has the former first lady’s tacit approval. Some involves outside groups that are operating independently, and at times in competition with one another, to prepare a final career act for the former senator and secretary of state, whose legacy as the most powerful woman in the history of American politics is already secure.

More than two dozen people in her orbit interviewed for this article described a virtual campaign in waiting — a term that itself makes some of Clinton’s supporters bristle — consisting of longtime Clinton loyalists as well as people who worked doggedly to elect her onetime rival Obama.

There are two spheres of influence. One is made up of more than a dozen Clinton staffers, loyalists and longtime friends whose advice she values the most.

The other sphere is more complex. It includes an assortment of super PACs and outside groups, all jockeying to be part of the Clinton movement but operating beyond her immediate direction and control. Still, some of these efforts could become the foundation of an eventual campaign.

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For all the genuine excitement about the prospect that Clinton, 66, could shatter the glass ceiling she famously invoked in 2008, the potential for rancor among these groups is real.

In at least one instance last year, two super PACs collided over efforts to get behind a Clinton candidacy — forcing her allies to intervene.

“There’s upside and there’s risk” to this patchwork of outside forces, said Tad Devine, an unaffiliated strategist who worked on John Kerry’s 2004 presidential campaign, when Democratic-leaning outside groups often acted at odds with the candidate’s message.

“The upside is that people are out there doing valuable and important work for you,” he said. But “in a campaign, when people are acting on your behalf but they’re not driven by an agreed-upon strategy, then that’s the risk.”

The outsiders: friends with headaches

Hillary Clinton was a few months removed from the State Department when one of her top aides, Huma Abedin, received an alarmed phone call about trouble brewing between two groups looking to help her politically.

“Ready for Hillary,” the super PAC that was initially billed as a grass-roots effort to channel early energy for Clinton to run, had become a source of frustration, and it was reaching a boiling point. In addition to a moniker that irked some Clinton allies — they thought it had an air of inevitability that plagued her in the past ­ — the group was making an aggressive play for activists and donors to back their effort.

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At the same time, Priorities USA, the main super PAC behind Obama in 2012, was in discussions to reinvent itself as a pro-Hillary Clinton endeavor. That would mean appealing to some of those same supporters. The two groups also had wildly different views of how active to be while Clinton was assessing whether to run.

The Priorities official warned Abedin that the situation could become problematic for Clinton if it wasn’t resolved. The official sought guidance from someone who had the would-be candidate’s ear.

The efforts of pro-Clinton outside groups over the past half-year, and the Clinton allies trying to corral them, reflect a much-changed political landscape since Clinton’s last run. Back then, super PACs didn’t exist. Potential candidates who needed campaign prep work done had to set up an exploratory committee or PAC under their own direct control.

Now super PACs are a must-have political accessory for candidates of all stripes.

The groups can raise and spend unlimited sums in support of a candidate and perform key tasks the person isn’t ready to do. In Clinton’s case, Priorities will probably line up pledges from big donors. Ready for Hillary is building email lists. And Correct the Record — launched last year by Clinton-critic-turned-defender David Brock as an offshoot of the super PAC American Bridge — hits back when Clinton is attacked in the media and tries to define potential rivals like Chris Christie.

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The outside backers have allowed Clinton to stay out of the political fray for a longer period of time as she makes up her mind about whether to run.

But the free-agent entities can also become headaches when they act at cross-purposes — or in ways a candidate doesn’t approve of.

A clash of super PACs

The call to Abedin, described by several people familiar with the conversation, touched off a larger debate in Clinton’s circle. Clinton herself was forced to grapple with the run-in between the two groups; several sources familiar with the discussions said she wanted to keep her team distant from the work of the super PACs to avoid brushing up against rules forbidding coordination. But Clinton made clear to aides that the mess, which in many ways echoed the factionalism of her past, needed to be sorted out.

In a series of meetings in Washington and New York, advisers to both groups huddled to address the problem. John Podesta, the former chief of staff to Bill Clinton who recently joined the Obama White House, was among the participants brought in on the Priorities side to help.

Some suggested trying to force Ready for Hillary to shut down. That idea was rejected out of concern it would prompt negative stories about Clinton forces stomping on the grass roots.

Another adviser proposed merging the two super PACs, but that also went nowhere.

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Eventually they settled on a solution: Ready for Hillary would focus on collecting and analyzing voter data, accepting donations up to $25,000. Priorities would be the super PAC for mega-donors, working solely on paid advertising.

Ready for Hillary has since won over key people close to Clinton impressed by its efforts like cultivating detailed lists of supporters through social media, which Clinton didn’t do in 2008. Among other moves, it brought on Craig Smith, a White House political director for Bill Clinton and friend from his Arkansas days. He gave the aura of an adult in the room to a group created by younger former Clinton staffers.

Most important is that Moore, whose background is in field organizing, is said to believe in the work the group is doing, as does Baker of Dewey Square, according to several sources. Besides the email list, Ready for Hillary is building a massive, 50-state direct-mail and voter targeting program. In a sign of cooperation, the group rented Clinton’s supporter list from her old PAC. It also brought on Obama’s field gurus, Mitch Stewart and Jeremy Bird, to help build up its efforts, including by supporting local candidates who Clinton backs in this year’s midterm elections.

Ready for Hillary hopes to make its data available to a 2016 Clinton campaign, and some Clinton allies believe there are a number of young aides and operatives working for the super PAC who could become part of her campaign. The 2008 campaign had many well-documented flaws, but one was the failure to prominently deploy young campaign talent, which flocked to Obama.

“If you wonder whether Clintonworld has learned our lessons from 2008, look no further than the work of Ready for Hillary,” said one source supportive of its work.

It’s far from certain the outside group’s voter data would be welcomed by a Clinton campaign; it will likely prefer to compile its own. Or, some Clinton associates say, it could choose from any number of outside campaign data firms, including two launched by Obama 2012 veterans after his reelection.

Elsewhere in the constellation of outside groups doing work related to Clinton is EMILY’s List, led by operative Stephanie Schriock, who is frequently mentioned as a possible Clinton campaign manager. The group, which focuses on electing women and isn’t a super PAC, is conducting an expansive polling project about attitudes toward female candidates. Correct the Record, the Brock-sponsored rapid response project, is being managed by a Hillary Clinton favorite, Burns Strider, and has her allies’ nod of approval.

“This effort for Hillary, unprecedented in both its early timing and scope, is a demonstration of the extent to which the Democratic Party is unified behind this potential candidacy,” said one of the organizers.

From Obama ‘08 to Clinton ‘16

Two of the boldest-faced names to enter the Clinton constellation in 2013 tied their political fortunes to electing Obama in 2008: Jim Messina, who went on to become a top political hand in the White House and then run Obama’s reelection, and Hollywood mogul Jeffrey Katzenberg.

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Despite his late arrival to Obama’s campaign in 2008 — he didn’t come on board until after the bloody primary — Messina was seen by Clinton aides as carrying a deep grudge from the campaign to the White House. Some Clinton associates suspected he was behind a failed attempt to scuttle two of her top staff picks at State: Capricia Marshall and Philippe Reines.

But what Messina lacks in longtime loyalty to Clinton, he makes up for in connections to Obama’s vast network of donors and activists. That had obvious value to a group like Priorities USA, which early last year was looking to morph from its 2012 version that decimated Mitt Romney with a series of attack ads into a pro-Clinton endeavor for 2016.

Early last year, Messina, who quietly admired Priorities’ work in 2012, started talking informally to the super PAC about a role. One draw is that working on a super PAC is less of a grind, and certainly more lucrative, than an actual campaign.

The discussions went on for months last year, long before news reports in November that he was in serious talks to become a co-chairman of the group. But some Clinton allies have grumbled that Messina’s swelling list of business clients could potentially embarrass Clinton; his backers dismiss the complaints as professional jealousy, saying plenty of Clinton advisers have their own potential business conflicts.

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The White House has its own worries about Messina’s hoped-for move. One is that it would look like Obama was giving his blessing to the pro-Clinton group as his own vice president, Joe Biden, is weighing a 2016 run. Concern within the administration about ruffling relations with Biden has been serious enough to cause a lengthy delay in signing off on Messina officially joining Priorities, according to two people familiar with the deliberations.

Whatever role Messina may end up playing in 2016, the mere fact that most Clinton allies are fine with him being part of a pro-Clinton group signals a rapprochement that began when Obama tapped Clinton as his top diplomat. Messina had informal discussions with some of her aides after 2012 about his view of modern campaigns, and Bill Clinton has publicly admired his work since developing a connection with him last year.

Messina wasn’t the only one affiliated with Obama to join the future Clinton army via Priorities. Katzenberg broke with the Clintons in 2008 to back Obama and four years later helped launch Priorities with a $2 million check.

“I hope my donation will draw attention to the amount of money being raised by the extreme right wing and serve as a catalyst for other Democratic donors,” the DreamWorks Animation chief executive told CBS News in April 2012. The super PAC is now broadly seen as his baby.

After Obama secured four more years, the Democratic rainmaker made clear he was prepared to get behind Clinton financially. With Priorities reinventing itself and Messina getting involved with the group — Katzenberg and Messina worked together during the 2012 race — the media mogul has positioned himself as the group’s ambassador to Hollywood.

If all goes as planned, the hope is that Katzenberg and Messina’s involvement on behalf of Clinton will signal a smooth passage from Obama to Clinton within the party.

“It reflects the fact that the Obama political infrastructure is seamlessly transitioning to serve as [Clinton’s] political infrastructure,” said California-based political strategist Chris Lehane. “And [it] sends a signal to both Obama donors and operatives that it is all right to begin actively supporting the Clinton ’16 effort.”

The don’t-do-it camp

Despite the feverish buildup to a Clinton candidacy, some of her closest advisers aren’t sure she’ll run ­— and some don’t want her to.

Clinton has as clear a path to the nomination as anyone could. But she also bears the scars from her 2008 battle, as do a number of her aides who remember vividly the toll the enterprise took on Clinton and everyone involved. They all want to help her achieve whatever she decides she wants, but they are clear-eyed about another campaign.

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Among their concerns: Why put herself through the campaign pulverizer again and risk ending her groundbreaking career on a low note? She could still wield plenty of influence from the outside ­— and enjoy a normal, fulfilling family life for the first time in who knows how long. People insist her health is not a worry, but it was just a year ago that she suffered a blood clot in her head after fainting.

Chief among those in the “no” camp is Clinton’s chief of staff at the State Department, Cheryl Mills, according to several people familiar with her thinking. Another close Clinton confidante, Maggie Williams, who took the helm of the 2008 campaign after a staff shake-up, is also said to have reservations for the same reason — the DNA-altering experience of a modern presidential campaign in which nothing is guaranteed.

The people cheerleading Clinton on the most are often less close to her. Their focus is primarily on winning ­ — they know Republicans probably won’t put up a candidate as weak as Romney next time and see Clinton as far and away their best shot.

Whatever their position, this much is true: From her most intimate associates to young activists just signing up, the majority are behaving as if a campaign will happen.

That doesn’t mean they’re certain it will. Her allies see the odds strongly in favor of another campaign but are also realistic that the world might look different in a year. Beyond potential health concerns, an unforeseen event could make running more complicated. Democrats could struggle mightily in the midterms, and Obama could have another difficult year. Another foreign policy headache could emerge, posing a fresh challenge for the former secretary.

Several sources said in interviews that her team is discussing how she will weigh in on policy debates over the course of the next year. She is working closely with clusters of aides on different policy initiatives — one involves child development, and Clinton is also being advised to address income inequality. Her memoir about her time at the State Department, initially expected for June, is likely to be out later in the summer, putting a book tour closer to the time when she would campaign for candidates in the midterms. That’s also closer to when she’s likely to announce her plans, after the November election.

“This is a very personal decision, one she has said she won’t be making anytime soon,” said Clinton spokesman Nick Merrill, when asked about the campaign presentation with Dewey Square consultants. Officials with the group declined to comment.

A place called Clintonland

The question hovering over all of these deliberations is what the 2016 version of the place called Clintonland ­ — a universe where proximity to the center is paramount and people have been known to exaggerate their closeness — would look like if she runs.

Her supporters maintain that some staffers whose voices should have been heard during the 2008 campaign were held back, and many of those people are advising her now. She didn’t lose 2008 by a lot, others point out, and not everything about the campaign was bad.

Still, the structure of some of Clinton’s past ventures, most notably the 2008 campaign, has been known to resemble less an org chart than a stew of dysfunction. She failed to establish clear lines of authority, bitter rivalries formed, and the principal ended up getting dragged into the chaos. Her world has historically been a ring of concentric circles of advisers, sometimes in competition.

Among the goals her supporters had when she left the State Department, one stood out: Send a message that she had absorbed the lessons of 2008. Many point to her tenure at the State Department as evidence that she had: Her staff — led by Mills along with Abedin, Marshall, longtime spokesman Reines and policy adviser Jake Sullivan — was generally seen as a well-functioning unit. Sullivan, who now works for Biden, would likely play a prominent role in a campaign.

One widely watched metric of change will undoubtedly be who from the last campaign returns. Of the six people most publicly identified with her last campaign, none is poised to return to their previous title.

The person from 2008 who’s asked about most is Mark Penn. Clinton’s pollster, chief strategist and message guru all wrapped into one, Penn was the person vilified the most by donors and operatives after she lost.

Rumors swirled among Washington operatives in the fall that Penn might be back as an important adviser to Clinton. He is said to still speak with the Clintons but is currently focused on corporate work.

“I’m all in with Microsoft as their executive vice president of global advertising and strategy and enjoying meeting new challenges there,” Penn said in an email.

Howard Wolfson, her longtime spokesman, just spent five years working for former New York City Mayor Mike Bloomberg. Phil Singer, a prominent 2008 spokesman, now advises New York Gov. Andrew Cuomo and could help establish an outside communications effort supporting her. Campaign manager Patti Solis Doyle, a Clinton lifer who bore blame internally over how she handled that role, is unlikely to be asked to rejoin, nor has she expressed interest in it. She went on to work for Obama and is now president of a financial services company.

Still, on e trait of Clintonland over the years is its ever-shifting roster. Someone on the outs one year can reemerge years later; proximity to the principal can change based on the needs of the moment. The list of former aides, friends and employees whose advice could be sought is virtually infinite for a couple whose worlds span three decades, two states and Washington, D.C.

One Clinton veteran likely to play an informal role if she runs is Neera Tanden, president of the liberal think tank Center for American Progress. She’s a key voice on progressive issues and shares a history with Clinton dating back to her 2000 Senate race, and she still speaks with Clinton.

Mandy Grunwald has been making ads and videos for both Clintons for decades, in addition to being an adviser. But Grunwald also worked on Elizabeth Warren’s successful 2012 Senate campaign and is still in the senator’s circle, making a possible return to Clinton harder to read.

It’s widely accepted that a second Clinton campaign would need and want fresh blood, too. One oft-mentioned possibility is Jen O’Malley Dillon, a deputy campaign manager for Obama. Another is Robby Mook, a young operative on Clinton’s 2008 effort who recently ran her friend Terry McAuliffe’s successful campaign for Virginia governor. Schriock and Guy Cecil, who rose within Clinton’s ‘08 campaign after a shakeup and is now overseeing the party’s efforts to keep the Senate in this year’s midterms, also come up repeatedly as potential 2016 hires.

One adviser predicted a “hybrid” of seasoned veterans as well as newcomers comprising a future campaign. Whouley, Baker and Moore may be doing some legwork now, but the people officially running a campaign would be a younger group.

What the talent pool can’t answer is what Clinton learned from last time; that will become apparent only once she brings on a political staff of her own, for a real campaign. Clinton made few new hires in the second half of last year and has not meaningfully expanded her team of paid political advisers since she left the State Department. That’s unlikely to change soon; anyone looking for a big burst of activity is likely to come away disappointed. Despite all the buildup in her name, Clinton herself is not acting like a candidate.

Chelsea and Bill

Everyone knows that there is no one closer to Hillary Clinton than her husband and daughter. What’s different these days is how Bill and Chelsea are now viewed when the conversation turns to questions about Hillary’s future.

In the run-up to the 2008 campaign, and even to the 2004 campaign, Democrats — not to say Hillary Clinton’s closest advisers — saw Bill Clinton as a colossal force behind his wife’s aspirations. But in the intervening years, Hillary has become as big a name in her own right, Chelsea has taken on a much higher profile and Bill Clinton has been, maybe only slightly, eclipsed by the women in his family.

In interviews for this article, just about every close Hillary Clinton ally, asked to describe who is at the top of her organizational chart, gives the same answer: Chelsea. Exactly what that translates into is shrouded in a bit of mystery. It would be hard to overstate the closeness between Hillary Clinton and her only child, who is known to have more of her mother’s signature caution and private approach, than her father’s more free-wheeling style. The extent to which she’s expanded her portfolio within their family foundation has surprised even longtime Clinton insiders.

But in terms of 2016, people close to the Clintons say it is difficult to divine whether Chelsea wants her mother to run.

In 2003, when some Clinton supporters urged her to jump into the race against George W. Bush, Chelsea Clinton disagreed. She told her mother she owed it to New Yorkers to complete her Senate term, as she had promised when she ran. It was a defining moment in Hillary Clinton’s political life.

Since then, Chelsea Clinton has become deeply involved in her parents’ work. She is a major presence at their family foundation, working for the last two years on a leadership change and hewing to many of her father’s philanthropic issue sets.

Chelsea Clinton has said the time she spent on the campaign trail for her mother in 2008 moved her to want to do more in public service. She could be very helpful in bridging a generational divide for her mother, who will inevitably face questions about her age. She’s put time into developing a social media presence.

But the 33-year-old New Yorker, who married in 2010 and recently hinted that 2014 could be the year she makes her mother a grandparent, has publicly tried to protect her mother’s right to just say no.

Asked in October if she’s like to see her mother become the first female president, Chelsea Clinton told Bloomberg News, “Before anything else, she is my mom. So I want her to do whatever she wants to do. … I am very strongly exercising my prerogative as a daughter to make sure my mom has this year to rest and reflect.”

Clinton herself has not exercised that prerogative very much since leaving State. She has been active giving paid speeches and collecting an unheard-of number of awards from groups who want to use her celebrity to highlight their causes.

For his part, Bill Clinton has been careful not to signal what he thinks his wife should do. People who spend time with the former president say he is animated in private conversations about 2016. He’s deeply aware of how super PACs have transformed the presidential landscape — for Democrats and Republicans. The unrecovered political addict still waxes on about poll numbers — not his wife’s, but in specific races he’s interested in, like this year’s Senate and governor races in Arkansas.

Yet these people say his tone toward his wife is deferential, and he’s made clear she is the person making the ultimate decision.

“I think, and she believes, that the country should spend at least another year working very hard on the problems we have,” Bill Clinton told CNN Español last month. “We have very serious challenges in America, and we have responsibilities around the world. I think it’s a big mistake; this constant four-year, peripatetic campaign is not good for America.”

At a Democratic Governors Association fundraiser that Clinton headlined in New York last year, the group’s chairman, Vermont Gov. Peter Shumlin, told guests before the former president spoke that Hillary Clinton will run for president and need their support, according to an attendee. Bill Clinton teasingly replied with surprise to hear his wife had made a decision.

A student of history, he is well aware of the legacy project a second Clinton presidency represents. But her loss in 2008 dented his foundation’s fundraising and imposed misery on all involved.

The misery that he himself contributed to is not generally cited as a concern these days. His off-message rants, legendary during that campaign, essentially disappeared during her four years at State. During that time, his wife finally established her own identity, a fact all members of the family seem aware of.

Bill Clinton has also continued to amass political chits that could be useful for Hillary down the road. He has endorsed a string of candidates running against people who did not back his wife in 2008. And he has weighed in on issues in ways that could be helpful to his wife, given the assumption people make that one is speaking for the other.

Hillary Clinton’s allies believe the timing is better for her now than in 2008. Warren is popular among the base, but she’s been adamant she’s not running, and if she did, it’s hard to imagine her taking the broader party by storm the way Obama did.

Still, when it comes to running a national campaign, 2008 is practically another era. Technology and social media have made things infinitely more complex and unwieldy than Clinton’s last experience.

None of this is lost on the would-be candidate or her allies.

At the Dewey Square Group meeting in her northwest Washington, D.C. home, Clinton received a rundown of key dates of a potential campaign as well as a sketch of TV advertising costs and other tasks that would be key to a second run.

It was all a reminder of just how much her life would be subsumed by another campaign.

“No one around her,” said one Clinton insider, “is under any illusions.”