Chasing Hillary

"Let us not grow weary, let us not lose heart, for there are more seasons to come, and there is more work to do." — Hillary Clinton's concession speech, capturing the resilience and fight that defined her career and campaign.

1. Hillary Clinton’s storied background set high expectations for her campaign.

Hillary Clinton entered the political contest as a household name with decades of experience. From serving as First Lady to Bill Clinton, to her roles as a US Senator for New York and Secretary of State under President Barack Obama, her credentials seemed impeccable. Her previous near-victory in the 2008 Democratic primaries had also primed her for what many believed would be her moment in 2016. Polls showed a 70% approval rating as the campaign ramped up.

Her reputation as a fighter for progressive causes like literacy, religious tolerance, and global health added to her appeal. Clinton's strong Methodist faith and advocacy for Jewish communities further emphasized her dedication to societal improvement. Her efforts consistently positioned her as a principled figure who could take on the country’s challenges.

However, name recognition and experience also drew scrutiny. Clinton’s layered history made her vulnerable to criticism that her candidacy was tied too closely to Washington politics. With entrenched media distrust and past Clinton family scandals like Whitewater resurfacing, the longstanding tension between her record and public perception prompted unintended challenges.

Examples

• Polling indicated her sky-high approval rates at the start of her candidacy in 2013.
• Clinton took strong moral stances, fighting for causes such as combating segregation and literacy during her career.
• The memory of prior Clinton controversies like Whitewater reminded voters of her entanglements with the political establishment.

2. A fraught relationship with the press hurt Clinton’s image.

Hillary Clinton’s evident distrust of the media emerged early, impacting her ability to tell her story effectively. Amy Chozick, assigned to cover Clinton for The New York Times, quickly sensed the animosity between the Clintons and the media. This reportedly stemmed from decades-old grievances, such as unfair treatment in prior scandals like Whitewater. Journalists frequently found themselves locked out of access to Clinton’s inner circle.

Hostility wasn’t limited to journalists questioning her ethics. A New York Times Magazine profile titled "Planet Hillary," which humorously depicted her orbit of aides and advisors, incensed her team. This strained relationship continued to alienate Clinton from positive opportunities to engage with the press, fostering an aura of secrecy instead.

This disconnect was compounded by criticism from her own supporters, who argued the press coverage often used subtle biases, portraying Clinton as “inevitable” or “insincere” and even branding such language as "coded sexism." Her team’s defensiveness further deepened media suspicion and amplified this cycle of resentment and miscommunication.

Examples

• Chozick’s profile in the New York Times Magazine upset almost everyone featured in it.
• The Clintons’ shaky rapport with key outlets like the New York Times dated back to the 1992 Whitewater Scandal.
• Clinton supporters labeled coverage of her as reductive and skewed by gendered assumptions.

3. The private email server controversy consumed the campaign.

One story relentlessly dogged Clinton: her use of a private email server while serving as Secretary of State. Initially exposed via a hacked email in 2013, the controversy escalated as investigations revealed that many of her emails had been deleted—sparking concerns about transparency. Clinton’s justification, claiming personal convenience, failed to quiet critics when the issue resurfaced throughout 2016.

Her attempts to respond, including a press conference where she claimed the practice had State Department approval, backfired. Rather than clearing the air, revelations that she’d erased around half her emails fueled accusations of cover-ups. The media fixated on the topic, overshadowing other policy discussions and reinforcing voter distrust.

The persistence of this story contributed heavily to Clinton’s inability to shift focus onto her platform. Despite clearing official allegations of wrongdoing, the public perception of secrecy and misjudgment left a lasting dent in her campaign.

Examples

• Clinton’s March 2015 tweet about email transparency gained immediate, widespread attention.
• Headlines like “What about your emails?” dominated the political discourse for months.
• The press interpreted Clinton’s delayed acknowledgment of mistakes as evasive, harming her image.

4. Clinton’s sense of humor often failed to resonate.

Behind closed doors, Clinton was sharp, witty, and good-humored. Yet, her public attempts to show this relatable side often misfired, either coming across as inauthentic or feeding into existing narratives. For instance, when asked about her emails, she joked about joining Snapchat because “those messages disappear all by themselves,” a tongue-in-cheek response that Republicans weaponized against her.

During select private events, Clinton’s humor shone. In a conversation about geopolitical tensions, she teased about giving a Republican red state to China—a rare instance of her using humor to connect effectively. Similarly, her playful pun urging voters to “Pokémon GO to the polls” charmed only a niche audience.

However, these moments diminished as her campaign wore on. Feeling the weight of scrutiny, Clinton became increasingly cautious. Journalists covering her campaign described a monotony that seeped into her public persona, with even harmless jokes often sidelined in fear of backlash.

Examples

• Her Snapchat remark about disappearing messages sparked further scrutiny of her emails.
• The “Pokémon GO to the polls” pun displayed her attempt to connect with younger audiences.
• Journalists covering her campaign noted its increasingly stiff atmosphere toward the election’s end.

5. Bernie Sanders presented an unforeseen challenge.

The Democratic primary saw Clinton battling much harder than anticipated against Bernie Sanders, whose campaign inspired a youthful movement. Sanders drew large, enthusiastic crowds, while Clinton’s events often struggled to fill venues. In addressing issues such as wealth inequality and health care, Sanders struck a nerve that Clinton’s prepared style couldn’t reach.

Clinton struggled to energize her base. Her campaign stops, such as a speech reminiscing about 19th-century figures like DeWitt Clinton, failed to resonate. Sanders, by contrast, relied on direct, populist messages, which proved more engaging.

The starker contrast between Sanders’s energized cheerfulness and Clinton’s controlled seriousness created an uphill battle. To downplay Sanders’s growing momentum, Clinton had to recalibrate her approach in subsequent primaries.

Examples

• Sanders regularly filled auditoriums with thousands, energizing young voters.
• Clinton referenced obscure historical figures, leaving audiences disengaged.
• "Feel the Bern" events highlighted the infectious excitement missing from her campaign trail.

6. Positive stories about Clinton were drowned out.

Some aspects of Clinton’s background could have bolstered her campaign, but they often became lost in public discussion. A standout example was her undercover work against school segregation in Alabama during the early 1970s. Masquerading as a housewife, she documented evidence that private schools actively excluded black students, courageously taking on racist institutions.

Despite these compelling narratives, Clinton seldom shared them herself. This reluctance, likely born out of a deep mistrust of the press, diminished opportunities to highlight her integrity and compassion. Even when Amy Chozick covered these stories with sensitivity, they struggled to compete with sensational headlines about her emails.

For the campaign’s detractors, Clinton’s cautious approach only deepened perceptions of her as inaccessible and calculating.

Examples

• Clinton’s 1972 work in Alabama uncovered private schools’ discriminatory policies.
• Segregation investigation highlights barely entered Clinton's campaign messaging.
• Her press team’s wariness with journalists hampered positive outreach.

7. Clinton’s religious faith revealed a deeper, more empathetic side.

Hillary Clinton's Methodist roots profoundly shaped her values and moral compass. She frequently visited black churches, delivering heartfelt speeches where her warmth and sincerity broke through. Quoting scriptures from James and Micah, she passionately emphasized justice, humility, and taking decisive action.

Clinton’s lifetime practice of attending church and her formative experience hearing Martin Luther King Jr. in 1962 underscored her commitments. Despite the power of this connection, the media often downplayed Clinton’s spirituality, choosing instead to mock her religious language as naïve when she spoke honestly about her beliefs.

If her team had embraced this aspect more openly, Clinton might have connected with voters in a way that felt more authentic and meaningful.

Examples

• Clinton avidly recited passages like James’s “Faith without works is dead” at key moments.
• Her lifelong Methodist practice, stretching back to her teenage years, shaped her worldview.
• Fear of derision for her faith caused her campaign to downplay a potentially relatable trait.

8. Clinton excelled as an underdog but faltered when ahead.

A moment of standout resilience came during the Nevada caucus effort. Faced with mounting pressure from Bernie Sanders, Clinton abandoned her polished, scripted image. In casual, unscheduled events with working-class voters, she displayed warmth and grit that resonated instantly.

Despite fatigue, she’s fondly remembered for moments like chatting with hotel housekeepers at Caesars Palace. This connection paid off: Clinton won a narrow victory. However, she soon reverted to being overly measured—a dynamic that many voters found uninspiring.

Moments like these showed the power of relating directly and emotionally, yet Clinton’s return to caution ultimately deprived her of gaining momentum.

Examples

• Clinton mingled with hotel staffers, creating genuine moments of connection.
• Her openness contrasted sharply with Sanders’s more polished rallies in Nevada.
• Organically built rapport translated to a caucus win over her nearest rival.

9. Media fixation on Trump denied Clinton room for her message.

Clinton was arguably the superior debater against Donald Trump during their televised face-offs. Pushing Trump into admitting questionable practices, such as exploiting tax loopholes, showed her sharpness. She also managed to expose Trump’s misogyny in moments like recalling his disparagement of Miss Universe winner Alicia Machado.

However, such instances often let Trump dominate headlines, sidelining Clinton’s core agenda. Discussions about job creation, health care, or reforms were overshadowed by coverage of her one-liners or Trump’s controversies. Facing a media landscape endlessly enthralled with Trump’s antics, Clinton struggled to recenter the narrative around her strength as a policymaker.

Examples

• Clinton highlighted Alicia Machado’s experiences to establish Trump’s misogyny.
• Trump’s contradiction during debates about tax avoidance stole media cycles.
• Clinton lacked the opportunity to fully promote her central platform issues.

Takeaways

1. Embrace transparency; avoiding tough topics can create an image of mistrust.
2. Prioritize building authentic, emotional connections with the audience.
3. Avoid allowing competitors’ antics to overshadow your message—control the narrative.