They Always Wanted Trump

 
Inside Team Clinton’s year-long struggle to find a strategy against the opponent they were most eager to face.

Aset of tables stood where the bed should have been in the 12th-floor Manchester hotel room Hillary Clinton’s aides were using as a New Hampshire war room. It was February 6 and their candidate was 44 miles east, desperately trying to excite New Englanders at a Portsmouth rally after limping out of Iowa essentially tied against her challenger.

But New Hampshire was a lost cause, and her team knew it. So instead of watching Clinton deliver a speech, members of her senior team huddled around a television in the room that served as a home base for campaign chairman John Podesta, manager Robby Mook, chief strategist Joel Benenson and communications director Jennifer Palmieri. They watched, in shock, as the man they had feared most as Republican nominee tanked under an assault designed to boot him from the GOP primary race.



By the end of the night, the narrative was set: Marco Rubio had just lost it all on the debate stage across town from that Radisson hotel room, stuck in a robotic delivery of canned lines under Chris Christie's brutal cross-examination.

In Brooklyn headquarters, staff in the 11th-floor nerve center called the Nevada room broke into giddy laughter every time the increasingly desperate Rubio repeated himself. But back in Manchester, the new reality hit Clinton’s inner circle like a ton of bricks—there might be no one left who could stop Donald Trump from clinching the Republican nomination.

“When Rubio got taken out in New Hampshire on the debate stage, that was a moment when I said, ‘OK, this looks like it,’” said former New Hampshire Democratic Party Chair Kathy Sullivan. “He was the golden child at that point, and then was just destroyed.”

“That’s when I realized that there was something bigger going on,” added one of Clinton’s longtime friends and advisers who remembers watching in disbelief, feeling in the moment that the ground was shifting underneath the campaign. Trump “is a master manipulator and a master of the counterintuitive. He knows exactly how to get things done. It’s disgusting to watch. But it’s effective.”

Even with that view emerging so early in the contest (it would be 16 more weeks before Trump clinched his party’s nomination), Clinton’s team would struggle in the ensuing months to land on a strategy that would stick. Within days of that February GOP debate, Clinton’s aides started considering how to redraw the battleground map it had been relying on for well over a year, assessing Colorado’s and Virginia’s swing-state status and re-running the numbers on suburban white women and young Latinos. They would direct the Democrat to try out, and ditch, one campaign slogan after another. And as she finally wriggled out of the primary to face Trump, the strategy was still evolving, producing dramatic tactical shifts — from embracing disaffected Republicans to firing up liberals, from previewing an uplifting closing stretch to savaging Trump with an unprecedented television ad barrage.
I asked a Clinton staffer about this. ... He said, ‘Well, you know, now we have to save the republic.’"

“I asked a Clinton staffer about this,” said Sullivan, who around that time briefly went online to research Irish double-citizenship out of her revulsion with the Republican nominee-to-be. “He said, ‘Well, you know, now we have to save the republic.’"

It was a great paradox after nearly a year of virtual certainty—and outright enthusiasm—about their ultimate opponent that her team would swing between overconfidence, denial and disbelief as it struggled to concoct an electoral formula for stopping Trump.

***

It was supposed to be Jeb Bush, if you asked Democratic honchos in mid-2015, except when it was always supposed to be Scott Walker. Eventually, they insisted, it was always supposed to be Rubio.

But it was never supposed to be Trump.

Clinton circles' initial planning for Bush began even before Democrats’ wipeout in the 2014 midterms. In an October 31, 2014 memo, informal confidant and longtime friend Sidney Blumenthal mapped out a “CONFIDENTIAL” path for Clinton, which she then forwarded to aides Nick Merrill, Brynne Craig, Huma Abedin, Philippe Reines and Cheryl Mills, with the note: “Worth discussing elements.” Mills then forwarded the note to campaign manager-in-waiting Mook and Podesta.




Chris Christie and Donald Trump share a laugh during a commercial break in the Republican presidential debate at St. Anselm College, which became famous for Rubio's "robot" gaffe. | Getty

“The Republican presidential campaign will begin on November 5th,” Blumenthal wrote. “If Jeb Bush doesn’t run, there is no viable establishment candidate. If he does run, he will be subjected to an unprecedented assault that might culminate in a splintered party, even a third party."

Around that time, an increasingly politically engaged Clinton started telling friends and political advisers that she expected something close to a classic battle about the economy against the Republican establishment’s choice.

Six months later, Clinton associates' wariness of Bush and his likely financial firepower was still acute: Democratic pollster Celinda Lake wrote to Clinton adviser Minyon Moore to warn her that she’d been testing Bush’s economic message for a client. “It has been remarkably strong. Getting even half of african americans and democrats and two thirds of latinos. Some thought it ended too harsh. But the perspective on the economy has really worked. Now we didn’t tell people this was from bush. But it’s a warning."

So to take Bush down, Clinton’s team drew up a plan to pump Trump up. Shortly after her kickoff, top aides organized a strategy call, whose agenda included a memo to the Democratic National Committee: “This memo is intended to outline the strategy and goals a potential Hillary Clinton presidential campaign would have regarding the 2016 Republican presidential field,” it read.

“The variety of candidates is a positive here, and many of the lesser known can serve as a cudgel to move the more established candidates further to the right. In this scenario, we don’t want to marginalize the more extreme candidates, but make them more ‘Pied Piper’ candidates who actually represent the mainstream of the Republican Party,” read the memo.

“Pied Piper candidates include, but aren’t limited to:
• Ted Cruz
• Donald Trump
• Ben Carson
We need to be elevating the Pied Piper candidates so that they are leaders of the pack and tell the press to [take] them seriously."

While the campaign also kept a close eye on Rubio, monitoring his announcement speech and tightly designing the tweeted responses to his moves, Clinton’s team in Brooklyn was delightedly puzzled by Trump’s shift into the pole position that July after attacking John McCain by declaring, “I like people who weren’t captured.”

Eleven days after those comments about McCain, Clinton aides sought to push the plan even further: An agenda item for top aides’ message planning meeting read, “How do we prevent Bush from bettering himself/how do we maximize Trump and others?"

They wouldn’t have to work very hard at it though; the debates were the beginning of the end for the candidate Clinton’s team always thought she would face on Election Day. The day after the first debate in August, Clinton confidante Neera Tanden emailed Podesta her analysis: “Bush sucked. I’m glad Hillary is obsessed with the one candidate who would be easiest to beat :) Besides Trump, of course.”

“Just like everybody, I thought this was a Bush against a Clinton, that’s all it was going to be,” said former Wisconsin Governor Jim Doyle. “When I saw the first set of debates, I would turn them on in an entertainment mode to see what Donald’s going to say today. It was funny."
Bush sucked. I’m glad Hillary is obsessed with the one candidate who would be easiest to beat :) Besides Trump, of course.”

Clinton aides finally started to see Trump as more than a tool to destroy Bush. In fact, Mook took him so seriously that his team’s internal, if informal, guidance was to hold fire on Trump during the primary and resist the urge to distribute any of the opposition research the Democrats were scrambling to amass against him. That hoarding plan remained in place deep into 2016 as some senior aides stayed convinced that a race against Trump would be a dream for Clinton, but as others kept insisting on tweaking the long-term plans against Rubio and Cruz—convinced the GOP would ultimately coalesce around the Floridian.

Much of the original playbook was still intact: As late as the last week of October 2015, a private memo from Mook to top bundlers invoked Bush’s fundraising power. And it wasn’t until the December holiday season — when Cruz and Trump emerged as pack leaders, and Podesta was telling fundraisers in closed-door meetings that he thought the Texan would win—that the team realized it was not prepared, strategically or tactically, for what many saw as a dream scenario.

If Trump was going to stay competitive, a rethink would soon be needed.

Trump’s dominance of cable news had already become a point of frequent discussion among Clinton aides, led by Palmieri and media adviser Mandy Grunwald, and senior staffers started to whisper to each other that a race against Trump would require a fundamental rebudgeting of the ad scheme to combat it—another look at the expected degree of negativity in the attack plan, a reconsideration of the markets on which to focus, and a conversation about the amount of money needed to fund the air assault.
The first time I realized that he [could compete] was when, after calling into Morning Joe and calling into CNN, he called into [another show]. ... He started to manipulate the media and change the media.”

“The first time I realized that he [could compete] was when, after calling into 'Morning Joe' and calling into CNN, he called into [another show]," said a former elected Democrat who remains in close contact with Clinton. "I said, ‘Wait a second, up until today, if the president—any president, George W. Bush, FDR, Eisenhower — if they were at the beach or decided they want to play golf but then their staff decided they had to go on TV, they couldn’t just say, ‘Let’s call in,’” “No. You have to go in. He started to manipulate the media and change the media."

***

That concern crystallized on January 28, when the then-front-runner skipped a GOP primary debate to hold an event of his own — and drew all the night's buzz and the next day’s headlines both in Des Moines and Washington. Bleary eyes across Brooklyn opened wider: Campaign pollster Benenson told friends that month that Trump was now on track to win.




Trump holds a rally for veterans the night of the GOP debate in Iowa in January 2016. | Getty

So too did Bill Clinton, who — increasingly the subject of Trump’s barbs at the time — was growing worried about his unpredictability. Personal friends told the candidate she should start preparing for an ugly fight against Trump, who in late December had just pushed her into a rare moment of public introspection as she spoke with a 10-year-old girl about bullying in Keota, Iowa, the afternoon after Trump said Clinton “got schlonged” in 2008.

Rubio’s high-profile crumbling shortly thereafter was the first inflection point: The Trump threat was more real than ever to Clinton’s operatives, who stepped up their paid research efforts and began more seriously discussing how a Trump electoral map would differ from Cruz’s. But a distraction in the shape of a 74-year-old Democratic Socialist Vermonter prevented Clinton from making a hard pivot.

The stretch immediately after New Hampshire was the darkest for Clinton, who suddenly faced the prospect of a substantially harder primary than expected while Trump started looking inevitable across the aisle, necessitating a rethink of her long-term electoral plan. Democrats with access to Clinton’s ear thought Cruz had a chance to turn his fortunes around once more Southern states voted in March, but much of the lingering doubt was eliminated on Super Tuesday, once Trump—like Clinton—took a slate of states as diverse as Massachusetts and Alabama after blowing through South Carolina and Nevada.

Clinton strategists' initial reaction to Trump’s blaze through the primaries at the time was giddy disbelief, but back in New York the anti-Trump plan and machinery was still barely begun.

“I know you can’t look past Bernie and March primaries,” senior Democratic strategist and Clinton veteran Joel Johnson wrote to Palmieri on February 26, one week after Trump won South Carolina and four days after he won Nevada. “But who is in charge of the Trump swift boat project? Needs to be ready, funded and unleashed when we decided — but not a half assed scramble."

The final Trump research book still was not finished.

And Clinton’s slow pivot away from Bernie Sanders and their expensive primary was far from over. Eager to begin the general election, she began speaking against Trump after the March 15 primaries—declaring, “our commander in chief has to be able to defend our country, not embarrass it” that night in West Palm Beach, Florida — but she quickly dialed back the effort when Sanders made clear he wasn’t going anywhere by kicking off a winning streak the next week.

While the ground team and inner circle focused almost entirely on dispatching Sanders, leading Clinton aides started to get more frequent updates on the anti-Trump polling and focus groups that studied the most potent lines of attack against the self-described billionaire, yet they resisted the seething series of entreaties from donors and allies in conference calls and private meetings to have the candidate start directly attacking Trump on the trail. Wary of appearing to be looking beyond Sanders’ challenge and keeping the example of Rubio’s demise in mind, Clinton’s camp remained terrified by the prospect of a seven-month schoolyard scrap.

“The longer you can avoid a brawl,” said veteran Clinton fundraiser and friend Alan Patricof at the time, referring to the nonstop calls for her to knife Trump early. “It’s distracting, it takes you into the gutter with him.”

While Clinton jumped from caucus state to primary destination, one of her most significant strategic shifts was just then starting to be designed back at headquarters.

***

A handful of Clinton’s leading strategists firmly insisted that Republicans would not nominate Trump until the moment Cruz bowed out, but Clinton confidants were by that point nonetheless convinced that they’d likely have to pair a Barack Obama-scale ground game with a pricey scorched-earth paid advertising campaign in the battleground states to overwhelm Trump’s television mastery. That would necessitate a nonstop focus on high-dollar fundraising from Clinton, her husband, and surrogates under the direction of finance chief Dennis Cheng. In the meantime, the question was where, exactly, that ad war would play out.

Clinton's discussions with other Democrats had for months revealed that she believed her path to victory relied on cutting a swath through the upper Mississippi and upper Midwest: a race against Bush or Rubio would make Florida much more difficult, and force her to lean more heavily on Michigan, Wisconsin, Iowa, Minnesota and Pennsylvania. In such an election, Virginia and Colorado would be squarely within the first tier of battlegrounds.

But the Democrat's polling showed that Trump’s appeal was fundamentally different from what she’d been planning for, requiring a large-scale shift in time and resources between the states.

His historic unpopularity among minority communities was one thing, but his stellar performances among less-educated Caucasian men also gave way to a steep drop off among college-educated whites. Facing an unprecedented opportunity for a Democrat among that group, Clinton’s strategists suddenly saw Colorado and Virginia look as blue as ever, with Iowa and Pennsylvania—and their higher concentration of lower-educated voters—taking their place as central swing states. GOP-leaning North Carolina and its growing population of recent college graduates joined that group before long. Florida was back on the table, too.

“Trump’s dominance with older high school-educated white males is remarkable. That’s a group that’s been trending away from the Democrats and toward Republicans for a long time. He has driven away college-educated whites,” said longtime Clinton strategist Paul Begala, an adviser to pro-Hillary Clinton super PAC Priorities USA Action. “So what Trump is doing—and this will be his legacy when he loses—is handing the suburbs to the Democratic Party."

Put more bluntly, according to a senior Clinton adviser who saw states such as Virginia, Colorado and Wisconsin removed from the top-tier discussion only in the early summer as Clinton’s battleground team advanced its budgeting and in-state advisers flew in for a Brooklyn huddle: “With [Trump’s] potential appeal as an instrument of revenge among white voters, it was clear early on that he would scramble the map."

The result was a flurry of activity in the states as they reshuffled their priorities and moved to hire operatives.

“To me it felt like they were—pre-Trump—not sure what they were going to do here,” said Steve Schale, Obama’s former Florida state director. “They had, at best, a skeleton crew here in the primary that left right after, and there weren’t a lot of calls going around to see who would staff, who was available."

In Pennsylvania, meanwhile, where Trump promised to compete, they mapped out a plan to drill down on Clinton’s advantage with the state's more educated voters.

“[Mitt] Romney was seen as acceptable in the Philadelphia suburbs. Hillary will win the suburbs by at least 250,000, double what Barack won the suburbs by. If the candidate was [John] Kasich or Rubio, there is no doubt in my mind that they would have kept Hillary to the same 120 [thousand] that Obama got,” said former Pennsylvania Governor Ed Rendell, an ex-DNC chair and longtime Clinton family friend.
I was in denial for a very long time,” added former Vermont Governor Howard Dean. ... I tell people I was wrong for 52 weeks in a row starting in June.”

Around early May, then, Clinton’s ad team drew up a plan to blanket the swing states soon after her still-raging primary against Sanders came to a close. Organizing resources flooded North Carolina, Florida, Ohio, and Pennsylvania by the end of the month.

The national polls started tightening. Legions of Trump skeptics fell away.

“I admit to being suckered into every narrative that predicted Trump’s demise over and over,” said Connecticut Senator Chris Murphy, a Clinton ally. “I admittedly was a pretty consistent skeptic that they were ultimately going to nominate this buffoon, so I probably came to the realization that he was the nominee as late as anybody."

“I was in denial for a very long time,” added former Vermont Governor Howard Dean, the one-time presidential candidate and DNC chair. “I tell people I was wrong for 52 weeks in a row starting in June.”

***

Until two weeks before the Republican convention in Cleveland, some Democrats in or near the Clinton headquarters argued vociferously for the campaign to maintain contingency plans in case GOP machers deciphered a way to oust Trump.

“The big fear in Democrats’ mind—and it wasn’t a huge fear, because it was entertaining to think about—was the chaos on the floor of the GOP convention if they tried to deny Trump the nomination,” explained South Carolina Democratic Party Chair Jaime Harrison.

That hesitance loomed large as Clinton started to turn more forcefully toward Trump, casting about for her message. The campaign’s concerted effort to start publicly defining Trump through coordinated candidate and surrogate communications began in earnest only in June—12 months after the celebrity had announced his campaign in the first place.

Aiming to replicate Obama's 2012 job of painting the public perception of Romney early (“stick the knife in” is how former Obama campaign chief David Plouffe described the goal to West Coast donors at the time), Clinton strategists looking at the focus group results settled on painting Trump as divisive—ditching the “risky” tag they had applied to Trump in May after Guy Cecil, head of the Priorities super PAC, sent a clear message to the campaign through a POLITICO interview that his group had found that such a description of Trump didn’t work.

Then, just days away from formally taking the nomination, Clinton dug in on the notion that Trump was unfit for the job, delivering a contempt-filled speech in San Diego that left the candidate herself feeling like she had finally cracked the anti-Trump code—a sentiment reinforced by the flood of private plaudits she then received from donors who’d spent the previous months predicting doom.

It was around that time that her team quietly made the last in a series of slogan switches, printing a batch of new campaign signage declaring, “Stronger Together”—but only after considering 83 other options, as outlined in an email attachment circulated to top aides nine months earlier. The previous iteration—“Fighting For Us”—disappeared without a trace.

It was far from the final tweak in a campaign that has since featured tonal shifts as dramatic as touting Meg Whitman’s support one month and directly wooing Sanders-voting millennials in a bid to stomp out any third-party troubles the next, as jarring as a mid-September shift to positive speeches while increasingly brutal negative anti-Trump ads continue to roll from ad strategist Jim Margolis’ team onto the air. As incongruous as spending months highlighting the separation between Trump and rank-and-file Republicans before turning on a dime to try and use him as an anchor to sink the rest of the party.

And now, with hours until polls close, Democrats’ yearlong divide is as deep as ever between those who see a once-in-a-generation opportunity to drive a stake through the Republican Party and those who think a mold-upending candidate like Trump has made for the toughest challenge in years. After all that, the final margin is unlikely to be a blowout, and it’s unlikely to be a squeaker.

But Clinton, at least, got the opponent her aides wanted, and a strategy to stick to.