Chasing Hillary

Chasing Hillary Plot Summary

Introduction

In the high-stakes world of political journalism, few assignments are as coveted or as grueling as covering a presidential campaign. For nearly a decade, one reporter found herself in the extraordinary position of chronicling Hillary Clinton's quest to shatter America's highest glass ceiling. What began as a temporary assignment in the frozen cornfields of Iowa evolved into a career-defining journey that would test professional boundaries, personal relationships, and journalistic ethics. Through blizzards and bus rides, hotel bars and campaign rallies, this intimate account reveals the complex dance between a guarded candidate and the press corps assigned to scrutinize her every move. The story that unfolds is not just about Hillary Clinton, though her enigmatic persona remains at its center. It's about the changing nature of political journalism in the digital age, the unique challenges facing women in politics, and the personal toll of witnessing history from an uncomfortable front-row seat. From the campaign's strategic miscalculations to the shocking election night conclusion, this insider perspective illuminates how ambition, gender, media dynamics, and unprecedented foreign interference collided to shape one of the most consequential elections in American history.

Chapter 1: The Reluctant Subject: First Encounters with Hillary

Hillary Clinton never wanted to be the story. Throughout her decades in public life, she approached the press with a mixture of wariness and resignation, viewing journalists as necessary obstacles rather than potential allies. This complicated relationship began long before her presidential ambitions emerged, shaped by the intense scrutiny she faced as First Lady of Arkansas, then of the United States. By the time she launched her first presidential campaign in 2008, Hillary had developed a protective shell that few reporters could penetrate. Early interactions revealed glimpses of the person behind the carefully constructed public image. During a rare unscripted moment on her campaign plane in 2008, Hillary accidentally walked in on a young reporter in the bathroom—a moment of human awkwardness that transcended their professional roles. Rather than retreating in embarrassment, Hillary laughed genuinely and later made a self-deprecating joke about it, displaying a warmth rarely seen in her public appearances. These fleeting connections stood in stark contrast to her typically guarded demeanor at press conferences and campaign events. The 2008 campaign established patterns that would persist throughout her political career. Hillary maintained a careful distance from the traveling press corps, preferring controlled environments where she could deliver her message without unexpected challenges. Her staff reinforced this approach, creating layers of protection that made spontaneous interactions nearly impossible. One senior aide explained the strategy bluntly: "She's been burned too many times. Why would she let her guard down now?" This defensive posture created a self-reinforcing cycle—the more Hillary withdrew, the more aggressive the press became in pursuing her, leading to further withdrawal. Despite these barriers, moments of connection occasionally emerged. During a campaign stop at a small diner in New Hampshire, Hillary engaged in a lengthy conversation with a waitress about healthcare costs, displaying genuine empathy and detailed policy knowledge. When the cameras moved away, she continued the discussion, revealing her authentic passion for the issue. Such moments offered rare insights into what motivated her beyond political ambition—a deep-seated belief that government could improve ordinary lives through practical policies. The relationship between Hillary and the press corps evolved over time, shaped by mutual disappointments and occasional breakthroughs. After her 2008 primary defeat, she adopted a more open approach as Secretary of State, earning praise for her accessibility during international trips. Journalists who covered her at the State Department described a different Hillary—more confident, less defensive, and occasionally willing to speak off the record about global challenges. This period represented a brief détente in her otherwise contentious relationship with the media. By the time she launched her 2016 campaign, however, old patterns reemerged. The email server controversy immediately placed her on the defensive, reinforcing her instinct to limit press access. As one longtime aide explained, "She believes most reporters are looking for gotcha moments rather than trying to understand her policies." This fundamental mistrust would shape campaign strategy throughout the election, creating a distance between candidate and press that proved difficult to bridge even in moments of crisis.

Chapter 2: Campaign Trail Realities: Life in the Traveling Press

The romantic image of campaign journalism—reporters and candidates engaged in meaningful dialogue while traversing the country—bears little resemblance to modern reality. For the journalists assigned to cover Hillary Clinton in 2016, daily life consisted of logistical challenges, physical discomfort, and the constant struggle to produce content under impossible deadlines. The "Boys on the Bus" era of campaign reporting had given way to what one female reporter called "Girls in Rental Cars"—a less glamorous but perhaps more accurate description of the predominantly female press corps following the potential first woman president. Physical hardship became the norm rather than the exception. Reporters routinely worked eighteen-hour days, subsisting on coffee and whatever food could be grabbed between campaign events. Sleep deprivation was so common that journalists developed a gallows humor about it, comparing their accumulated sleep debt and celebrating rare nights with more than five hours of uninterrupted rest. The toll on health was significant—weight gain from stress eating and irregular meals, voice strain from shouting questions at press conferences, and a perpetual state of exhaustion that compromised both physical and mental wellbeing. Transportation between events created its own unique challenges. For the first ten months of the campaign, the Clinton team didn't provide a press bus, forcing reporters to chase the candidate's motorcade across Iowa and New Hampshire in rental cars. This led to dangerous situations—journalists checking email while driving, racing through unfamiliar terrain in bad weather, and occasionally getting lost and missing events entirely. One reporter nearly drove into a frozen lake during a New Hampshire snowstorm while following directions to a campaign stop. Even after the campaign finally provided a bus following a tragic accident involving a volunteer, the accommodations were spartan compared to other campaigns. The financial burden fell heavily on individual reporters and their news organizations. Campaign coverage required significant investment—rental cars, hotel rooms, meals, and unexpected expenses like emergency dry cleaning or replacement equipment. One reporter calculated that her news organization spent over $200,000 to keep her on the trail for the duration of the campaign, a figure that raised questions about the sustainability of this model of political journalism. Smaller outlets simply couldn't afford comprehensive coverage, creating an access gap that favored larger, better-funded news organizations. Despite these challenges, the traveling press corps developed its own culture and community. Competitors became confidants through shared experience, developing friendships that transcended professional rivalries. They created inside jokes about campaign quirks—referring to the carefully selected "ordinary citizens" at Clinton events as "Everydays" after her campaign slogan about "Everyday Americans." When reporters needed to interview these voters, they would plead with staffers: "C'mon, my editors need me to quote some Everydays." This gallows humor helped maintain sanity amid the grueling schedule. The gender dynamics within the press corps reflected broader changes in political journalism. Unlike previous campaigns covered predominantly by men, the Clinton press corps was majority female—a shift that changed both the atmosphere and the coverage itself. Female reporters brought different perspectives and questions, particularly regarding work-life balance and gender issues. However, they also faced unique challenges, including online harassment from trolls who targeted women covering Clinton with particular viciousness. This created additional pressure on female journalists to prove their objectivity while covering the first viable female presidential candidate.

Chapter 3: The Media Game: Access, Control and Mutual Distrust

The relationship between Hillary Clinton's campaign and the press corps operated according to unwritten rules that both sides understood but rarely acknowledged openly. Access became the ultimate currency—reporters needed it to do their jobs effectively, while the campaign used it strategically to shape coverage. This dynamic created a perpetual negotiation where journalists constantly sought more access while campaign staff carefully controlled information flow to advance their narrative. Clinton's press operation was dominated by a rotating cast of male aides whom reporters collectively referred to as "The Guys." These handlers acted as gatekeepers, determining which reporters received information and opportunities for interaction with the candidate. Their tactics ranged from charm to intimidation, from selective leaks to outright hostility. When reporters published stories the campaign disliked, The Guys would flood their inboxes with complaints, often timing their calls for maximum disruption—Friday nights or Saturday mornings when editors were unavailable to provide support. The campaign maintained extensive dossiers on journalists, tracking their coverage patterns, personal backgrounds, and potential vulnerabilities. One reporter discovered her file included notes about her social media activity, personal relationships, and even her coffee preferences—intelligence gathered to help the campaign manage the relationship more effectively. This level of surveillance created an atmosphere of paranoia among the press corps, with reporters wondering what information the campaign had collected about them and how it might be used. For Hillary, the press represented a necessary evil rather than a potential asset. She viewed journalists primarily as obstacles to overcome rather than conduits to voters. This perspective emerged clearly during a rare off-the-record drinking session with reporters in Manchester, where she delivered a soul-crushing critique of political journalism. She described reporters as gossip-mongers uninterested in substantive policy issues, more focused on personalities and horse-race coverage than the actual impact of political decisions on ordinary lives. While her frustration was understandable, this attitude reinforced the distance between candidate and press. The email server controversy exemplified the dysfunctional relationship between Clinton and the media. What began as a legitimate story about compliance with government records requirements quickly spiraled into an all-consuming narrative that overshadowed policy discussions. Clinton's initial response—a defensive press conference at the United Nations where she appeared irritated by the questions—only intensified media interest. Her team's strategy of limiting information and controlling the narrative backfired spectacularly, creating a vacuum that speculation and conspiracy theories rushed to fill. By the general election, Clinton had gone more than 270 days without a formal press conference, a fact Trump's campaign highlighted daily. This strategy may have limited damaging stories in the short term, but it also prevented Clinton from developing the relationships with reporters that might have humanized her to voters. The contrast with Trump's media approach was stark—while he attacked the press publicly, he remained remarkably accessible, calling reporters directly and giving frequent, freewheeling press conferences. This created an asymmetry in coverage that ultimately worked against Clinton's interests.

Chapter 4: Personal Costs: When Politics Consumes Everything

The all-consuming nature of campaign reporting exacted a heavy personal toll that extended far beyond professional challenges. For journalists assigned to cover Hillary Clinton, the boundary between work and personal life didn't just blur—it effectively disappeared. Relationships suffered, health declined, and major life decisions were postponed indefinitely as the campaign demanded total commitment. One reporter described the experience as "putting your entire existence on hold for the duration, with no guarantee of when or how it would end." Romantic relationships proved particularly vulnerable to the campaign's demands. The constant travel, unpredictable schedule, and perpetual exhaustion made maintaining connections nearly impossible. Phone calls with partners were frequently interrupted by breaking news alerts or campaign developments that required immediate attention. One journalist recounted how her relationship ended after she missed her boyfriend's birthday celebration for the third consecutive year due to campaign events. "He finally said he couldn't compete with Hillary Clinton for my attention, and honestly, he was right," she explained. Those whose relationships survived developed elaborate systems for maintaining connection—scheduled FaceTime calls during rare breaks, shared online calendars to track potential visit opportunities, and understanding partners who accepted the reality of campaign life. Health concerns became normalized to a disturbing degree. Reporters developed elaborate systems for managing chronic conditions on the road—carrying extra medication, finding doctors in unfamiliar cities, scheduling virtual appointments during rare breaks in the campaign schedule. Physical ailments were discussed with dark humor: back problems from carrying equipment, digestive issues from irregular eating, voice strain from shouting questions at press conferences. More concerning were the mental health impacts—anxiety, depression, and burnout became so common they were barely acknowledged as problematic. One reporter described having panic attacks in hotel bathrooms before forcing herself to appear composed at campaign events. The financial impact extended beyond immediate expenses to long-term financial planning. Major life decisions—buying homes, starting families, pursuing advanced degrees—were postponed indefinitely as the campaign consumed all available resources and attention. One journalist calculated that her retirement contributions had effectively ceased for the duration of the campaign, creating a financial setback that would take years to overcome. Another delayed fertility treatments until after the election, only to discover that the postponement had significantly reduced her chances of conceiving. Perhaps most significantly, covering Hillary Clinton meant sacrificing personal identity to become part of a narrative not of one's own making. Reporters found themselves cast as characters in the Clinton campaign story—alternately villains, obstacles, or occasionally useful tools—rather than independent observers. This role assignment created a disorienting professional experience where objectivity became increasingly difficult to maintain amid the pressure to produce content, break stories, and maintain access without becoming either adversary or advocate. The psychological impact lingered long after the campaign ended. Many journalists described a form of post-traumatic stress that made readjustment to normal life challenging. Having lived in a world where every development seemed consequential and every moment potentially historic, returning to ordinary reporting assignments felt anticlimactic. Relationships damaged during the campaign proved difficult to repair, and the physical toll required months of recovery. One reporter summarized the experience: "I gave two years of my life to covering Hillary Clinton, and I'm still not sure what I got in return besides an ulcer and a broken engagement."

Chapter 5: Email Storms and Russian Shadows: Coverage Challenges

The email server controversy that dominated Hillary Clinton's 2016 campaign began with a seemingly routine story. In March 2015, The New York Times broke the news that Clinton had exclusively used a private email server during her tenure as Secretary of State. What initially appeared as a technical compliance issue quickly metastasized into a character question that would haunt her candidacy until Election Day. Behind the scenes, Clinton's team grossly underestimated the story's staying power. "This will be gone in a week," one senior advisor confidently predicted during an early strategy session. That miscalculation led to a disastrous press conference at the United Nations where Hillary's defensive posture and technical explanations only intensified media scrutiny. The moment crystallized a fundamental campaign weakness: the inability to recognize when transparency might serve better than control. Rather than providing complete information upfront, the campaign released details incrementally, creating the impression they were hiding something even when they weren't. Each new revelation—from the existence of classified information to the deletion of emails deemed personal—fueled a narrative of secrecy and evasion that proved impossible to shake. For journalists covering the campaign, the email story created professional dilemmas. The public clearly had an appetite for email-related coverage—stories on the topic generated enormous traffic, prompting editors to demand more. Yet many reporters privately questioned whether the issue deserved the overwhelming attention it received. "I never agreed with Hillary that her email server was a nonstory, especially after the FBI opened its investigation, but I would regret—and even resent—that it became the only story," one journalist later wrote. This tension between journalistic responsibility and market demands created uncomfortable pressures on reporters trying to maintain perspective. The Russian hacking operation that targeted Democratic officials added another layer of complexity to campaign coverage. When WikiLeaks began releasing emails stolen from campaign chairman John Podesta in October 2016, journalists faced an unprecedented ethical dilemma: how to report on newsworthy information obtained through what intelligence agencies would later identify as a foreign intelligence operation designed to influence the election. Most news organizations proceeded with coverage, rationalizing that the information was already public and therefore newsworthy, regardless of its origins. This decision would be scrutinized extensively after the election. Many journalists who had covered the stolen emails expressed regret about potentially serving as unwitting accomplices in a Russian influence operation. "We became vectors for Russian intelligence simply by doing our jobs," one reporter observed. The experience prompted painful reflection about journalistic responsibilities in an era of information warfare, with many news organizations subsequently developing new protocols for handling hacked materials. The contrast between coverage of Clinton's email practices and the emerging evidence of Russian election interference revealed troubling media dynamics. While the email server story received relentless attention despite its relatively technical nature, the unprecedented foreign attack on American democracy initially struggled to gain traction. When Clinton directly accused Russia during the second presidential debate, saying "We have never in the history of our country been in a situation where an adversary, a foreign power, is working so hard to influence the outcome of the election," her warning was largely dismissed as a political tactic rather than a genuine national security concern. This coverage imbalance reflected broader challenges in political journalism—the difficulty of explaining complex, novel threats compared to familiar narratives about political scandal; the pressure to appear balanced even when evidence wasn't equivalent; and the tendency to view new information through existing frames rather than recognizing paradigm shifts. These factors combined to create a media environment where Clinton's emails received substantially more coverage than Russian interference, a disparity that would later prompt institutional soul-searching among major news organizations.

Chapter 6: Trump's Rise: Witnessing the Pied Piper Strategy Backfire

In the early days of the 2016 campaign, the Clinton team viewed Donald Trump as an asset to their strategy rather than a serious threat. Internal strategy documents revealed what they called the "Pied Piper" approach—elevating extreme candidates like Trump to make the entire Republican field appear radical by association. "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," read one memo to the Democratic National Committee. This calculation reflected a fundamental misreading of the political moment that would have catastrophic consequences. For the first ten months of her campaign, Hillary traveled the country effectively propping up Trump, portraying him as the unbridled id of the GOP. After Trump called Mexican immigrants rapists and criminals, she told Democrats in Little Rock that there was "nothing funny about the hate he is spewing," but quickly added that Trump was merely saying in harsh terms what the rest of the Republican candidates believed. The campaign's communications team repeatedly emphasized that all Republican candidates were "cut from the same cloth," inadvertently legitimizing Trump as a serious contender rather than an outlier. The contrast in how the media covered Trump versus Clinton revealed troubling double standards. In 2007, Clinton had been criticized for using a chartered helicopter—dubbed the "Hill-A-Copter"—to campaign across Iowa, with commentators calling it a symbol of her elitism. Yet when Trump gave rides to children on his customized Sikorsky S-76B helicopter at the Iowa State Fair, the political class marveled at it as evidence of his marketing genius. "The Trump Copter became indicative of his connection to the people. He was the Everyman's billionaire," one reporter observed. This pattern repeated across numerous aspects of campaign coverage. Trump's relationship with the press, while openly hostile, paradoxically gave him advantages that Clinton lacked. His accessibility—giving impromptu press conferences and calling reporters directly—created opportunities for unfiltered communication that Clinton's controlled approach prevented. His willingness to say outrageous things guaranteed media attention, while Clinton's careful statements often failed to break through the noise. The economic incentives of digital media further skewed coverage—Trump generated clicks and ratings that translated directly to advertising revenue, creating institutional pressures to maintain focus on his provocative statements. By the time Clinton's team recognized the threat Trump posed, it was too late. Their strategy of elevating him had worked too well, and their subsequent attempts to reposition him as dangerous rather than merely extreme lacked credibility after months of different messaging. A close Trump aide later told a reporter that after watching Clinton's fumbling press conference about her email server, Trump knew he could beat her. "He knew he could throw Bill's past back at her and she couldn't say a word," the aide explained. The Pied Piper had turned the tables. The campaign's internal polling consistently underestimated Trump's appeal, particularly in Rust Belt states that would ultimately decide the election. Data analysts focused on traditional metrics while missing the emotional connection Trump established with voters who felt abandoned by both parties. At a rally in Pennsylvania, one reporter observed a level of enthusiasm that defied conventional political analysis: "These weren't just supporters; they were believers." This quasi-religious fervor contrasted sharply with the more transactional relationship many voters had with Clinton, creating an enthusiasm gap that raw polling numbers failed to capture.

Chapter 7: Making History: Gender Politics on the Campaign Trail

On June 7, 2016, Hillary Clinton took the stage at the Brooklyn Navy Yard wearing white in honor of the suffragettes who had fought for women's right to vote. "Thanks to you, we've reached a milestone—the first time in our nation's history that a woman will be a major party's nominee for the president of the United States," she declared to a cheering crowd. The historic achievement came nearly eight years to the day after she had conceded to Barack Obama in the 2008 primary, ending her speech then with the observation that while she had not shattered "that highest, hardest glass ceiling," thanks to her supporters, "it's got about 18 million cracks in it." Clinton's relationship with feminism and gender politics evolved significantly between her two presidential campaigns. In 2008, her team had downplayed gender, with strategist Mark Penn advising her to run "as a man" and emphasize strength and experience over breaking barriers. By 2016, she embraced the historic nature of her candidacy more openly, though still cautiously. When she finally secured the nomination, Clinton devoted the victory to her mother, Dorothy, born on June 4, 1918, the same day Congress passed the Nineteenth Amendment. "I wish she could see her daughter become the Democratic nominee for president of the United States," she said, fighting back tears. Throughout her career, Clinton faced criticism that would rarely be directed at male politicians. Her voice was too loud or too soft; she was too emotional or too cold; too ambitious or not inspiring enough. When she attempted to joke about her email server controversy, the backlash was swift and severe. These double standards reflected the challenges facing women in politics more broadly. As one female senator told Clinton, "The public will allow a man to have a much broader emotional range than a woman. We all know this. A man can cry; we all feel sorry for him. If a woman cries, she's finished." The campaign struggled with how much to emphasize the gender milestone. Some advisors worried about alienating male voters, while others saw it as Clinton's most compelling narrative. This tension was evident when Hollywood friends Linda and Harry Thomason created a biographical video highlighting the women who had paved the way for Clinton's historic run. Campaign strategists rejected it, preferring a more broadly appealing message about "breaking down barriers" rather than shattering glass ceilings. This caution reflected the campaign's broader tendency to prioritize safe messaging over emotional connection. For female journalists covering Clinton, the campaign raised complex questions about gender and objectivity. They faced misogynistic harassment from online trolls while navigating their own complicated feelings about covering the first viable female presidential candidate. When Clinton secured the nomination, female reporters posed for a photo, celebrating the historic moment they had witnessed, even as they maintained their professional distance. This moment captured the unique position they occupied—simultaneously participants in and chroniclers of a potential turning point in American history. The gender dynamics of the general election became particularly fraught after the release of the Access Hollywood tape in which Trump boasted about sexual assault. Clinton's team struggled with how forcefully to respond, aware that appearing too angry risked triggering stereotypes about emotional women. During the second debate, when Trump loomed behind Clinton as she spoke, she later wrote that she considered turning around to say, "Back up, you creep," but instead maintained her composure. This moment exemplified the narrow emotional bandwidth permitted to women in politics—expected to be both strong and likable, assertive but not aggressive.

Summary

Hillary Clinton's presidential campaigns represented a profound collision of personal ambition, gender politics, media dynamics, and unprecedented external interference. Her journey offers valuable lessons about resilience in the face of setbacks, the double standards women continue to face in public life, and how the relationship between politicians and the press has fundamentally changed in the digital age. Though her presidential ambitions went unfulfilled, Clinton's campaigns permanently altered the landscape of American politics, making it easier for future generations of women to imagine themselves in the highest office in the land. The story of chasing Hillary ultimately reveals as much about American democracy as it does about Clinton herself. It exposes the tension between our idealized vision of how campaigns should function and the messy reality of modern politics—where access is currency, authenticity is performance, and the relationship between candidates and the press resembles a dysfunctional marriage neither party can escape. For journalists who devoted years to covering Clinton, the experience prompted difficult questions about their profession: how to maintain objectivity while witnessing history, how to balance professional demands with personal wellbeing, and how to serve readers without becoming unwitting participants in narratives crafted by campaigns or foreign adversaries. These questions remain unresolved, awaiting the next generation of reporters who will chase future candidates through the cornfields of Iowa and beyond.

About Author

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Amy Chozick

Facebook: https://www.facebook.com/amychozickAmy Chozick is a New York-based writer-at-large for The New York Times and a frequent contributor to the Times Magazine, writing about the personalities and power struggles in business, politics and media. Prior to that, she led the paper's coverage of Hillary Clinton’s presidential campaign. ​Before joining the Times in 2011, Ms. Chozick spent eight years at The Wall Street Journal where she was a foreign correspondent based in Tokyo and covered Hillary and Obama's 2008 presidential campaigns.​In 2017, Ms. Chozick received the William Randolph Hearst Fellows Award. She is also the recipient of a Front Page Award for beat reporting and has been recognized by the Society for Feature Journalism Excellence-in-Features Writing Competition.​Ms. Chozick served as a consultant on the Netflix political drama, “House of Cards,” advising the writers on the development of the female journalist characters. She was recently profiled in Vogue and Cosmopolitan and interviewed on Fresh Air with Terry Gross.​Born in San Antonio, Ms. Chozick moved to New York in 2001 with no job, no apartment and a stack of clips from The Daily Texan. She lives on the Lower East Side with her husband and son.

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