Skip to content

10 Moments That Shaped the Path to Election Day

Not all the turning points toward the Clinton-Trump showdown made the headlines


Every national campaign has a unique rhythm and historic consequence, but the one climaxing Tuesday is destined to stand out. The United States is going to choose its first woman president, or else its first president without any experience as a public servant.

And the path the nation took to this extraordinary moment is sure to be revisited for years by historians as well as satirists. That’s guaranteed by the over-the-top personalities of the principal characters, their complicated paths toward this day and the disgusted, bewildered, impassioned and sometimes bemused attitudes of the electorate.

Summarizing it all — especially just before the decisive denouement — is impossible. But the events on these 10 days were pivotal in setting the biggest storylines of this year’s race for the presidency.

Jan. 13, 2009

Hillary Clinton took a symbolically rich early step on her path toward a potentially historic triumph, remarkably on the same day as there were secretive steps on a course that could prove her ultimate undoing.

The whole world got to see her bask in the first moment, when she offered a characteristically thorough review of world hot spots and U.S. diplomatic complexities as the Senate Foreign Relations Committee considered her for secretary of State. Barack Obama’s unexpected decision to put his rival for the 2008 Democratic nomination in the Cabinet’s most prestigious seat gave Clinton a new lease on political life, and her prominence for the following four years cemented her standing as the default choice to succeed Obama and become the nation’s first female president.

No one saw what was happening 260 miles away, where an aide was registering the online domain to a server in the basement of the Clintons’ home in Chappaqua, New York. The public did not know for another six years that she used this private system exclusively for conducting State Department business including the receipt of classified material.

That decision, combined with her frequently changing versions of events and the tortuous FBI inquiry, has become the ultimate Exhibit A for the millions of voters who have come to view Clinton as arrogant at best and criminally culpable at worst.

June 10, 2014

One of the most stunning primary election upsets in congressional history heralded a huge opening for a candidate like Donald Trump.

Eric Cantor lost the Republican primary in a Virginia district surrounding Richmond, the first House majority leader denied renomination since the leadership job was created in the 19th century.

Challenger Dave Brat (who still holds the seat) ran a campaign that in hindsight looks like a template for this year’s Republican national standard-bearer: He excoriated the incumbent as an avatar of the establishment, more beholden to his big-money donors and the lobbyists on K Street than to constituents struggling to adapt to a changing economy. He derided Cantor’s support for liberalized global trade, and he lambasted his “pro-amnesty” willingness to consider an overhaul of immigration laws that might include a path to legal status for some in the country illegally.

Cantor’s defeat showed that a mainstream GOP leader with unlimited funding at his disposal could be outmatched by the underfunded passions of the infuriated and disenfranchised. It also re-energized the tea party wing of the House Republican Conference, leading to Speaker John A. Boehner’s forced departure a year later just as Trump was consolidating his standing as the nation’s pre-eminent combative outsider.

March 30, 2015

Elizabeth Warren firmly closed the door on running for president, leaving Bernie Sanders to step up from the left’s junior varsity squad and become Clinton’s only progressive alternative.

Organizers of both the liberal group and a political action committee created to draft Warren for president packed the Barnes & Noble on Manhattan’s Union Square, hoping to press the Massachusetts senator toward entering the race. Instead, after promoting the paperback edition of her memoir, she answered the first audience question with the Shermanesque statement they were dreading.

“I am not running for president, I’m not going to run for president. I am working my fanny off every single day on the key issues that I think matter in this country,” she said. “I’m doing it every day. I have this place now in the Senate.”

Given how close the Vermont senator came to upsetting Clinton for the Democratic nomination, it’s easy to imagine Warren succeeding at what Sanders could not quite do. As a relative political newcomer with a telegenic affect, and a woman too, she would probably have been a much better messenger for advancing his anti-old-guard, populist message.

July 18, 2015

Trump went before a gathering of social conservatives and started proving he could get away with defying all political conventional wisdom.

A month before, he’d announced his candidacy with a speech that had outraged the nation’s fastest-growing demographic group, Latinos, by calling Mexican immigrants “rapists.” Still, he was in a statistical tie for first with Jeb Bush in a 16-person field, at 15 percent support among Republican voters. And then he decided to insult John McCain.

“He’s not a war hero. He’s a war hero because he was captured. I like people that weren’t captured,” Trump said of the Arizona senator at the Family Leadership Summit in Ames, Iowa.

Denigrating the party’s 2008 nominee, and also the epitome of bravery for millions of veterans (another essential voting bloc) for his time as a prisoner of war in Vietnam, would have been electoral suicide for almost any candidate.

Instead, it was at that moment he started securing the firm hold on first place in the polls — gaining 10 points in the next three weeks — that he never relinquished despite an ever-lengthening roster of inappropriate and angry utterances that would have almost surely destroyed almost any remotely conventional candidacy.

Feb. 6, 2016

Marco Rubio earned the dismissive nickname “Marco Roboto,” crippling his bid to finish second in New Hampshire and thereby position himself as Trump’s principal establishment alternative.

Polls had shown the Florida senator surging ahead of the other four candidates realistically vying for second place. But during a nationally televised debate the Saturday night before the primary, he inexplicably repeated — four times — close variations of the same talking point: “Let’s dispel this notion that Barack Obama doesn’t know what he’s doing. He knows exactly what he’s doing. He is trying to change this country.”

The crowd in the hall groaned by the third time, and social media lit up with mocking mashups.

Rubio ended up in fifth, never regained momentum and withdrew in March. Gov. John R. Kasich of Ohio got the runner-up spot he’d said was essential to staying in the race, soon becoming the only candidate with a mainstream conservative background. But he never got ahead of tea-party-aligned Sen. Ted Cruz of Texas as the principal Trump alternative. Had Rubio shuffled his note cards and come in second in the Granite State, it’s easy to imagine big donors and establishment GOP leaders uniting to transform him into the candidate who stopped Trump.

March 15, 2016

Clinton swept all five big-state primaries on “Separation Tuesday,” halting a burst of Sanders momentum and expanding her delegate lead to an almost mathematically-insurmountable amount.

A week earlier, Sanders had narrowly won Michigan in the biggest upset of the 2016 nominating contests. But the monstrously funded, excessively organized and relentlessly on-message Clinton campaign juggernaut did not deviate from plan, and she ran the board in Florida, Ohio, North Carolina, Illinois and Missouri — demonstrating her staying power in the Rust Belt and the South’s two biggest general election prizes.

By winning 58 percent of the day’s pledged delegates, she expanded her lead to more than 320 — a margin Sanders never meaningfully shrank, though half the delegates were still up for grabs.

In her victory speech, Clinton tacitly acknowledged the tipping point by test-driving themes for the fall: “We should be breaking down barriers, not building walls. We’re not going to succeed by dividing this country between us and them. You know, to be great, we can’t be small. We can’t lose what made America great in the first place. And this isn’t just about Donald Trump, all of us have to do our part.”

May 5, 2016

Speaker Paul D. Ryan refused to endorse Trump after he effectively clinched the nomination, an extraordinary rebuke foreshadowing an intensified Republican civil war that neither of the nation’s two top Republicans has benefited from.

Cruz and Kasich suspended their campaigns, ending the prospects for a contested July convention in Cleveland, after Trump won a surprisingly strong victory May 3 in the Indiana primary. But when the presumptive nominee called for the party to unify behind him, Ryan bluntly said he was “just not ready to do that” because Republicans want “a standard-bearer that bears our standards” and Trump had not yet run a campaign “that they’re proud to support and proud to be a part of.”

Trump, characteristically, took less than an hour to offer a combative rejoinder, declaring himself as “not ready to support Speaker Ryan’s agenda.”

A dozen or more approach-avoidance confrontations later, Ryan was willing to say he voted in Wisconsin for Trump but rarely spoke the name aloud. He’d given the House GOP rank-and-file license to abandon Trump, and three dozen did so. He’s made clear he still views the nominee as temperamentally unsuited for the presidency and not reliably conservative enough to lead the GOP. The Trump forces have sent strong signals that, whether he wins or not, he won’t try to stop the festering efforts to oust Ryan from the top job at the Capitol.

Aug. 25, 2016

Obama’s approval rating topped 50 percent and hasn’t dipped lower since, giving Clinton a political green light to tap him as her most powerful surrogate.

Historically, the American electorate has proved reluctant to give either party a lease on the White House of more than eight years. Clinton, in fact, would be the first Democrat since Harry Truman in 1948 to win a presidential election following another Democrat’s multiple-term administration.

The previous two-term president, George W. Bush, and his 25 percent approval rating in the fall of 2008 were a significant drag on McCain and GOP lawmakers running down-ballot. (The party lost eight Senate seats and 21 House seats.) But the fact that Obama has been viewed favorably by a majority of Americans every day for 10 consecutive weeks (according to Gallup) cannot hurt Clinton and the prospects for decent Democratic gains in Congress.

His standing has also given him license to spend much of the campaign’s final month stumping in swing states for Clinton and against Trump, using increasing passionate rhetoric. He sought to boost turnout by the “Obama coalition” — African-Americans, Latinos and young people, especially — by traveling to Nevada, Pennsylvania, Ohio twice, North Carolina three times and Florida four times.

And that was before Monday’s finale, a whirlwind trip in which he barnstormed Michigan and New Hampshire before flying in to Philadelphia to stand by his would-be-successor’s side at an election-eve rally.

Sept. 28, 2016

FBI Director James B. Comey promised Congress the agency would reopen its Clinton email investigation if new information came to light, presaging his astonishing announcement that whipsawed the campaign’s final 10 days.

Comey said in July the inquiry was completed and no prosecution was warranted. This infuriated Republicans, who summoned him for a browbeating at the House Judiciary Committee just before decamping for the campaign trail, where he was pressed to remain amenable to reopening the investigation.

“We would certainly look at any new and substantial information,” Comey promised.

And exactly a month later, 11 days before the election, he told Hill leaders that potentially pertinent emails had been discovered in an unrelated investigation — into whether former Rep. Anthony Weiner of New York, the estranged husband of top Clinton aide Huma Abedin, had been sexting an underage girl.

Former Justice Department officials of both parties labeled the move unwarranted, unfair and against longstanding polices for preventing the FBI from tipping the electoral scales. And having “email, “Clinton” and “FBI” newly strung together in headlines proved the most problematic “October surprise” for her campaign. But Comey’s vow to lawmakers boxed him in: He would have been open to career-ending accusations of politicization by the Republicans if word of the new emails had gotten out while the FBI was keeping its inquiry under wraps.

The same vow, however, also committed the director to entering the heart of the political system just two days before Election Day — telling Congress “never mind” as soon as his agents finished their around-the-clock scouring of the Weiner-Abedin laptop and finding nothing there.

Oct. 9, 2016

Trump flatly denied ever acting sexually inappropriately, behavior he’d bragged about on an “Access Hollywood” outtake — prompting at least 13 women to begin coming forward to say they’d been kissed or groped against their will.

“No, I have not,” he declared in the opening moments of the second presidential debate, when asked if he had ever done any of the things the country had heard him boasting of two days before. That was when a 2005 videotape became public in which he described to the TV host Billy Bush kissing women and grabbing their genitals without permission and getting away with because “when you’re a star, they let you do it. You can do anything.”

Trump repeatedly dismissed his comments as regrettable “locker room talk.”

But during the following two weeks, a diverse collection of women described encounters with Trump, from the 1980s until a decade ago, very similar to what he’d first described and then denied. The roster included several businesswomen, several beauty pageant contestants, a makeup artist, a journalist, a receptionist, a pornographic film actress and a contestant on his “Apprentice” show.

They alleged Trump had made unwanted contact on a cross-country flight, at nightclubs, at a California golf resort, in his New York office, at the U.S. Open tennis tournament, backstage at the David Letterman show, in pageant dressing rooms and several times at his Mar-a-Lago complex in Florida.

Trump has categorically denied all their allegations, in some cases asserting he’d never met the women and sometimes suggesting they were not attractive enough to merit his attentions.

And, while none of the instances has been proved or disproved, collectively they kept alive the fall’s most damaging story involving Trump until the close of a campaign in which the relative breadth of his electoral “gender gap” could prove decisive.

Recent Stories

Former Justice Sandra Day O’Connor, first woman on the Supreme Court, dies at 93

Members want $26 billion for programs the Pentagon didn’t seek

Expelling bee — Congressional Hits and Misses

Appeals court rejects Trump push to dismiss Jan. 6 suits from lawmakers, police

Photos of the week ending December 1, 2023

House expels Rep. George Santos