Taylor Gee is an editorial researcher at Politico.

On Saturday evening, when the New York Times released its explosive report that Donald Trump had claimed a $915 million loss on his 1995 taxes and possibly hadn’t paid federal taxes in the 18 years that followed, it was a clear sign that the election had entered a new phase. Though the revelation itself was astounding, the timing was anything but: Less than a day into the new month, 2016’s first “October surprise” had arrived.

Political history is littered with the charred remains of such late-in the-election bombshells that scramble political calculus just as the stakes are at their highest. An “October surprise” can be happenstance or deliberately orchestrated; international (e.g. the outbreak of war) or domestic (e.g. a massive economic rally). Sometimes it’s personal, with a long-hidden skeleton spilling out from a candidate’s closet. It can save a political campaign as quickly as it can wreck one. And occasionally, it can even decide an election and set the course of the nation.


With four weeks left in the October and one surprise down already, it’s quite possible that there will be shockers yet to come—with Russian hackers, Donald Trump’s penchant for controversy, Julian Assange on the prowl, Hillary Clinton’s missing emails and a precarious scenario in the Middle East, it is anyone’s guess.

And when the next October surprise is revealed, it will join a rich history of last-minute revelations. Some wreaked havoc on elections and upended races, others reinforced the inevitable. Some were manufactured and expertly timed, others were the product of happenstance. But hearing them is enough to sober up even the most confident election observer: an election isn’t over until it’s over.

1840: Just Another Electoral Fraud

Late into his campaign for reelection, President Martin Van Buren had a trick up his sleeve that he thought would secure him a second term in office: Federal prosecutors planned to charge top Whig politicians in New York with a “most stupendous and atrocious fraud” in which they paid Pennsylvanians to travel to New York and fraudulently vote multiple times in the state’s 1838 elections. The prosecutors, members of Van Buren’s Democratic party, did not announce the charges until mid-October, aiming to maximize the indictment’s electoral impact. Democratic newspapers jumped on the story, running sensationalist headlines like, “A Gigantic Plot to Elect Harrison By Fraud” and “Sound the Alarm. Your Liberties Are In Danger.”

At first, the Whigs denied the accusation, but then one of the voter-fraud scheme’s organizers admitted to the charges. The electorate's reaction, however, was not as explosive as Van Buren hoped: They simply assumed that the Democrats were up to the same shenanigans, even though the Whigs were the only ones prosecuted. Van Buren lost the election by six points.

1880: A Forged Letter

On October 20, 1880, the New York Truth published a three-sentence letter purportedly written by Republican nominee James A. Garfield. The note, addressed to an H.L. Morey of Lynn, Massachusetts, voiced support for Chinese immigration to the U.S., and expressed the opinion that employers had the right “to buy labor where they can get it the cheapest.”

Chinese quarter of San Francisco, California, c.1880s. | Getty Images

The published letter came in the context of widespread xenophobia among white Americans, and both the Democratic and Republican platforms—as well as Garfield himself—had endorsed restrictions on Chinese immigration. The Morey letter threatened to paint Garfield as duplicitous and jeopardized his support in western states whose white citizens were particularly fearful they would lose their jobs to Chinese immigrants.

While Democratic operatives quickly distributed half-million copies of the Morey letter, Garfield was slow to defend himself—due, in part, to the fact that he was initially unsure whether or not he had authored the letter. Penmanship experts began scrutinizing the correspondence to determine its authenticity, and reporters made their way to Massachusetts to track down the addressee, an unknown H.L. Morey of Lynn. Reporters never found Mr. Morey, and after examining the letter himself, Garfield felt confident it was not his handwriting and publicly announced that it was a fake.

Even with Garfield's eventual denial, the scandal hurt him politically. What was supposed to be a clear Republic victory became a close race. Garfield beat his opponent by only .02 percentage points in the popular vote, and he lost California, the state most affected by Chinese immigration. After the election, the letter's author was revealed to be Kenward Phillip, a New York Truth journalist who was later arrested and indicted for fraud.

1884: “Rum, Romanism and Rebellion”

In 1884, James G. Blaine, the Republican presidential nominee from Maine, attended a GOP meeting in October when a Presbyterian minister named Dr. Samuel Buchard accused the Democrats of representing “rum, Romanism, and rebellion” — that is, alcohol, Catholics, and the Confederacy.

Blaine didn’t object, a silence he later claimed was because either couldn’t hear the comment or wasn't paying attention. But that didn't matter: the public furor that followed cost Blaine thousands of votes from anti-prohibitionists, Roman Catholic immigrants, and southerners. The comment energized Irish voters in New York to vote against Blaine in droves, likely costing him the state—and with it, the election.

1912: A Bottomless Ticket

President William Howard Taft’s doomed 1912 reelection campaign faced difficulties from the beginning: not only did Democratic New Jersey Governor Woodrow Wilson represent an electoral threat, but Theodore Roosevelt, Taft’s Republican predecessor, split off from the GOP to run on the Bull-Moose ticket, splitting the allegiances of Republican voters nationwide.

One week before Election Day that November, Taft endured a final blow: His vice president, James S. Sherman, died of Bright's disease while at home in Utica, New York. More than three million Americans ultimately voted for the deceased vice president, although it was decided beforehand that Nicholas Murray Butler, the president of Columbia University, would receive the votes in Sherman’s place. In the end, it didn’t matter: The Taft-Sherman campaign would receive a mere eight electoral votes, finishing far behind both Wilson, the victor, and Roosevelt.

1920: Black Warren G. Harding and FDR's Investigation Into Homosexuality

Weeks before the 1920 campaign, a racist professor from Ohio started the rumor that Warren Harding was partly African American. | Getty Images

It seemed inevitable that Warren G. Harding would be elected president, but in the weeks before the election, his campaign was dismayed by the spread of a rumor that Harding had “Negro blood.” When Mrs. Harding heard about the rumor, she reportedly wept until she was red-eyed. The charge came from William E. Chancellor, a famously racist professor at Wooster College. Harding's advisers were worried the falsehood would hurt their candidate among white racists in southern states, and went to great lengths to prove Harding’s European ancestry. It was, in a sense, the 1920 version of the modern “birther” conspiracy theory.

While the Harding campaign was busy trying to prove their white credentials, the Democratic ticket was embroiled in its own scandal. Before accepting the vice presidential nomination that year, Franklin Roosevelt was the assistant secretary of the Navy. In that capacity, Roosevelt had authorized an investigation of homosexuality at a naval facility in Newport, Rhode Island. The investigative unit, which directly reported to Roosevelt, told its members to participate in homosexual acts in order to gain firsthand evidence that would stand up in court.

When Roosevelt learned of the investigative unit’s methods, he canceled the operation, but when the operation’s details went public, Roosevelt came under fire as the official who authorized the unit’s mission. John Rathom, a prominent newspaper editor from Providence, led the charge against FDR, and in October, Rathom additionally alleged that Roosevelt had allowed 83 seamen convicted of “unnatural acts” to return to duty. The accusation proved baseless, but the incident did little to help the Democrats stop Harding from taking the White House in November.

1940: FDR Loses the Black Vote, Then Wins it Back

In 1940, President Franklin Roosevelt was worried about holding onto the black vote as he competed for an unprecedented third term in office. As Europe descended into war, FDR came under criticism from African-American leaders for enabling the military's continued segregation. He was facing a general-election opponent, Wendell Willkie, with a strong civil rights platform. To cap it off, less than a month before the election, an FDR press aide named Stephen Early kneed a black police officer in the groin outside of Madison Square Garden in New York City, a move seen as both an attack on a black professional and an example of the double-standard treatment afforded to Washington insiders.

FDR announced the creation of the Tuskegee Airmen, an African American aerial fighting unit, shortly before the 1940 election in which he faced an opponent with a strong civil rights platform. | AP Images

To mitigate the political damage, Roosevelt responded with an October surprise of his own: Days before the election, Roosevelt promoted Colonel Benjamin O. Davis Jr. to brigadier general — the first African American to reach that rank – and announced the creation of the Tuskegee Airmen, World War II’s famous group of African-American military pilots.

The ploy largely worked, and Roosevelt won with 55 percent of the popular vote, losing only in white-collar, Protestant communities.

1964: International Events Trump a Sex Scandal

The term “October Surprise” came into popular use in 1972, but the election of 1964 experienced one of the most surprising Octobers in electoral history. It started out on October 7, when LBJ top aide Walter Jenkins was arrested for disorderly conduct with another man in the Washington D.C. YMCA, which the Toledo Blade later described as “so notorious a gathering place of homosexuals that the District police had long since staked it out with peepholes for surveillance.” Within two days, someone in the FBI had leaked the story to the RNC. “For 24 full hours, Republicans and Democrats alike held their breath to see how the nation would react,” wrote the Toledo Blade, analyzing the election a year later. “And perhaps the most amazing of all events of the campaign of 1964 is that the nation faced the fact fully – and shrugged its shoulders.”

LBJ escaped the sex scandal in part because October wasn’t yet over, and the Jenkins incident would soon be swept aside by even greater surprises—this time on a far more consequential stage. On October 14, one week after Jenkins’ arrest, Soviet Premier Nikita Khrushchev was ousted from power by his hardliner colleagues in the USSR. In the two days that followed, the United Kingdom’s Labour Party won a majority in parliament and the People’s Republic of China conducted its first nuclear weapons test. Amid international tumult, Goldwater’s inflammatory rhetoric seemed even less appealing than it already had. In November, President Johnson won in a landslide.

1968: Nixon Derails LBJ’s Vietnam Peace Talks

William Casey, a Nixon aide later credited with coining the term “October Surprise,” was suspicious that as the 1968 election raged, President Johnson would try to engineer a last-minute peace deal in Vietnam in an attempt to throw the election to Vice President Hubert Humphrey. Casey was right to be suspicious—shortly before the election, LBJ announced a halt to bombing and the start of new peace talks between Saigon and the Viet Cong. In the polls, Humphrey briefly pulled ahead of Richard Nixon.

When Nixon heard of Johnson’s maneuvering, he responded by reaching out to South Vietnam’s president Nguyen Van Thieu through backchannels, encouraging him to not attend peace talks and assuring him that if Nixon won the presidency, South Vietnam could expect stronger support from his administration than it would get from Johnson or Humphrey.

It’s difficult to know if Nixon’s outreach influenced President Thieu’s decision, but Nixon got what he wanted: Three days before the election, the South Vietnamese withdrew from the peace talks, and Humphrey lost his momentum. By that point, LBJ had learned that Nixon was interfering in international affairs and had began wiretapping the Nixon campaign. Humphrey chose not make Nixon’s actions public, however, and lost to his Republican opponent on Election Day.

1972: Nixon (Prematurely) Announces Peace Agreement in Vietnam

Four years later, President Nixon still hadn’t fulfilled his campaign promise to end the Vietnam War. A timely breakthrough came on October 8, when North Vietnamese negotiators in Paris suddenly agreed to U.S. conditions for peace.

Henry Kissinger announces "Peace is at hand" days before Nixon's re-election. | AP Images

National Security Advisor Henry Kissinger rushed from Paris to Washington for a press conference scheduled for October 26. On October 22nd, things began to fall apart: South Vietnam told Kissinger they would not accept the agreement, and North Vietnam subsequently took offense to Kissinger’s request for more time to persuade Saigon and publicly accused the United States of duplicity. None of that stopped Kissinger from attending the scheduled press conference, however, and proclaiming that “peace is at hand.” The announcement pushed Nixon even further ahead in the polls, and won the election with more than 60 percent of the popular vote. The peace negotiations, however, fell apart in December 1972, and the Vietnam war would continue for another two-and-a-half years.

1980: Iran Holds Carter’s Campaign Hostage

In the Carter-Reagan election, October Surprises entered the world of conspiracy theories. As the story goes, Ronald Reagan was worried that a last-minute deal to release the American hostages in Iran would give President Jimmy Carter the support he needed to win reelection. Then, days before U.S. voters cast their ballots, Iran announced that the it would not release the hostages until after the election.

Allegations quickly took root over the cause of Iran’s statement. Jack Anderson of the Washington Post claimed that President Carter had been planning a military operation to save the hostages, hoping it would save him the election. Others alleged that Ronald Reagan had made a secret deal with the Iranians to postpone the hostage release and rob Jimmy Carter of victory.

That November, Reagan defeated Carter, and Iran continued to hold 52 Americans hostage, releasing them mere minutes after Ronald Reagan completed his inaugural address in January 1981. Political figures and hostages themselves demanded a probe into the timing of the incident, but Congress didn’t bite until later, when two congressional investigations found no evidence of a conspiracy between Reagan and Iran. Still, a few high-profile figures, including former Iranian President Abulhassan Banisadr, stand by the allegations of a secret Reagan-Iran deal to this day.

1992: A Poorly Timed Iran-Contra Indictment

The Iran-Contra affair, when the Reagan administration illegally sold weapons to Iran and used the money to fund an anti-communist militia in Nicaragua, came to light in 1987, but by the fall of 1992, it was still fresh enough to cause electoral trouble for Republicans.

Just four days before the Bush-Clinton-Perot election, independent counsel Lawrence E. Walsh indicted former Reagan Defense Secretary Caspar Weinberger for lying about his involvement in the Iran-Contra scandal. Republicans fumed, accused Walsh of timing Weinberger’s indictment to damage President Bush’s re-election chances, even though Walsh himself belonged to the Republican Party. In November, Bush lost the election, but before he left the Oval Office, he pardoned Weinberger.

2000: George W. Bush’s DUI

George W. Bush and Al Gore were tied in national polls in the days leading up to the 2000 presidential election, but then Fox News Channel broke the biggest scandal of Bush’s campaign: 24 years earlier, Bush had been arrested for a drunk-driving in Maine.

Though the Bush campaign told reporters that the incident was so long ago that it would do little to change voters’ minds, ten years later, Bush strategist Karl Rove wrote that he believes the scandal cost Bush five states. Though many would question that math—and it’s difficult to argue with a counter-factual—Rove believes that without the DUI news, Bush would have won the popular vote and the mess in Florida would have been avoided.

2004: A New Bin Laden Video Boosts Bush

On October 27, 2004, Osama bin Laden released a video claiming responsibility for the 9/11 attacks and calling President Bush a dictator who repressed freedom by means of the Patriot Act.

On October 30th, 2004, Osama bin Laden released a video finally admitting his involvement in the 9/11 attacks. | Getty Images

The video renewed public interest in national security and aided Bush. By targeting Bush for criticism, Bin Laden cast him in the role of his enemy—a title that Americans would welcome—while reiterating criticisms of the Patriot Act that many of Bush’s domestic political opponents had made.

2008: A Market Crash Causes McCain’s Unforced Errors

In October 2008, the stock market's decline accelerated, joblessness reached a 14-year high, and the global economy teetered on the brink of disaster. Americans were beginning to feel the effects of the Great Recession, driving up Bush’s already-high unpopularity as his tenure in the White House came to an end.

The economic downturn spelled the end of McCain's candidacy. In the months prior, the senator had been struggling to relate to the economic grievances of voters: In an August 2008 interview with POLITICO, McCain couldn't recall how many houses he owned, promising “I’ll have my staff get back to you.” Then in September, he paradoxically declared that “the fundamentals of our economy our strong” while simultaneously recognizing the “tremendous turmoil in our financial markets and Wall Street.” In an effort to appear steady at the helm, he suspended his campaign to return to Washington to focus on the crisis — a move that backfired, making him look ineffective and unable to take on more than one task at a time.

Obama capitalized on the moment and McCain’s gaffes, propelling him through the campaign season's final stretch and to the White House.

2012: A Secret Video Tape

Hurricane Sandy has been falsely labeled an October Surprise during the 2012 election, but it fails to qualify because it was not a human-caused event. The real surprise of that fall 2012 was the September release of a secretly recorded tape of Mitt Romney belittling nearly half of America while speaking to wealthy donors at a closed-door fundraiser.

“There are 47 percent of the people who will vote for the president no matter what. All right, there are 47 percent who are with him, who are dependent upon government, who believe that they are victims, who believe the government has responsibility to care for them,” Romney said at a private, high-dollar fundraising event.

The Obama team quickly made the audio recording the center of a swing-state ad blitz that aired through October. In an interview with David Letterman shortly after the clip surfaced, President Obama quipped, “My expectation is that if you want to be president, you've got to work for everybody, not just for some.”

Not even Romney could deny how bad it was for his campaign. “That hurt,” Romney told Fox News’ Chris Wallace in an interview four months after the election. “There’s no question that hurt and did real damage to my campaign.”