“Beware the Ides of August,” warned David Wade, a former longtime aide to Secretary of State John Kerry. “Now it is a definitional period.”

No matter how much Trump insists voters won’t make up their minds until after Labor Day, strategists of both stripes warn that late summer is when negative narratives of a candidate can be indelibly impressed upon the electorate.

WASHINGTON — Donald Trump, take heed. While the waning days of summer may be when many Americans trade loafers for flip-flops, the lulling August waters are traditionally treacherous for aspiring presidents — especially ones already running behind.

Just ask Kerry, the 2004 Democratic nominee. He was famously videotaped windsurfing off the coast of Nantucket that summer, providing Republicans fodder for a political ad about his views shifting “whichever way the wind blows.”


John Kerry, then the Democratic presidential candidate, windsurfed off Nantucket in 2004. The Republican Party used windsurfing footage of Kerry to create an ad labeling the then-senator as a flip-flopper. Laura Rauch/Associated Press/File

Or former governor of Massachusetts Mitt Romney, the 2012 Republican nominee, whose off-the-cuff statements casting doubt on London’s readiness to host the summer Olympics overshadowed a European tour that was supposed to boost his foreign policy credentials.

Or Senator John McCain, who in August 2008 told a reporter that he could not recall how many houses he owned. (The answer: eight, at the time.) Instead, the Republican nominee said, “I’ll have my staff get to you,” prompting Democratic rival Barack Obama to brand the Arizona senator as out of touch with everyday Americans.

“The dog days of August could end up dogging a presidential campaign well beyond August because of how it impacts the story lines,” said Chris Lehane, a veteran Democratic political strategist. “Most of these candidates have just one moment during the summer. Donald Trump has one on a daily basis, which is a deep, dark, dank, unspinnable place to be in.”

To win in November, Trump, who has fallen perilously behind in polls following a string of self-inflicted wounds, must overcome historically daunting odds.


He trails Democratic challenger Hillary Clinton in national polls by nearly seven points, according to the average calculated by Real Clear Politics. If he bounces back, he will be a rarity. Candidates who were ahead in the polls following the political conventions won the popular vote in the last 16 elections, according to Christopher Wlezien, a government professor at the University of Texas at Austin.

Trump’s poll numbers plummeted following his nominating convention in Cleveland, once he attacked the Muslim parents of an Army captain who died in combat. His rocky summer worsened with a series of comments that were seen as irresponsible or outrageous: He suggested that gun owners take action against Clinton if she’s elected, and falsely accused President Obama and Clinton of literally founding the Islamic State terrorist organization.

In the first case, Trump said he was “obviously” referring to the political power of Second Amendment advocates; and in the second, he said he was just being sarcastic. In both cases, he blamed the media for misconstruing his words.

There are signs Trump is trying to dig his way out of his summer swoon. He shook up his campaign leadership this week, the second time in two months. But even that move leaves a negative impression on voters.

“Since Trump locked up the nomination, through this entire summer, what he’s done is validated a lot of people’s greatest worries about him with one mistake after another that will feed this really negative narrative about his candidacy for the next few months,” said Kevin Madden, a Republican strategist who worked for Romney in 2012 and for the 2004 George W. Bush campaign.

August has a history of sinking candidates, Madden noted, speaking gleefully of the Kerry windsurfing windfall that the George W. Bush campaign used to cement the then-Massachusetts senator’s image as a “flip-flopper” on issues from the Iraq War to education reform.


“Every single day, in every single way, we made the Kerry campaign pay for the windsurfing debacle,” Madden said.

Trump and his forces say they are undaunted by his current standing in the polls, which show him sliding behind Clinton by double digits in some swing states. They are optimistic about making up the deficit as they transition to building a ground game in those battleground states, having already fallen months behind Clinton in opening field offices, hiring staff, organizing volunteers, and airing ads.

“It is August when people are probably more interested in why the water is green in the swimming pool in Brazil right now,” said Bob Paduchik, Trump’s Ohio director. “That attention is going to shift around Labor Day.”

Trump opened his first wave of field offices in Ohio just last week. In Florida, where his campaign huddled last Friday with Republican National Committee officials to plot a path forward, Trump will belatedly open two dozen offices by Labor Day. He plans to start airing his first television ads on Friday.

But is it already too late?

“Right now, I don’t see a ground game or an air game in the most important battleground state that is a must win,” said Al Cardenas, former chairman of the Florida Republican Party. “At this window in time, Florida looks like an elusive target.”

Trump supporters caution against underestimating voter enthusiasm for the outsider during an unprecedented campaign cycle in which the New York real estate mogul has broken virtually all political norms and expectations. But many Republicans doubt the effectiveness of a strategy that hinges on the candidate’s cult of personality, massive rallies, and sheer will to dominate the news cycle, for better or for worse.


“The guy has been further trapped in the summer time,” said John Kingston, a former Romney donation bundler from Winchester who is funding a third-party effort to defeat Trump. “Barring any unforced errors by Secretary Clinton, there is no chance for him to redeem his image.”

But there’s always September.

Lest anyone think Clinton will be on safer ground past Labor Day, consider 1988. Then-Massachusetts Governor Michael Dukakis, the Democratic nominee, emerged from his convention with a 17-point lead in the polls over then-Vice President George H.W. Bush, the Republican nominee.

While Bush later received his own post-convention bounce, Dukakis cemented his campaign’s demise shortly after Labor Day by trying to appear tough by donning a helmet and riding in a tank.

Bush won that November — in a landslide.

Then-Massachusetts Governor Michael Dukakis cemented his political demise in 1988 by trying to appear tough by donning a helmet and riding in a tank. Michael E. Samojeden/Associated Press/File/1988/Associated Press

Tracy Jan can be reached at tracy.jan@globe.com. Follow her on Twitter @TracyJan.