PHILLY SPECIAL — When former President Donald Trump and Vice President Kamala Harris take the stage in Philadelphia this evening, they’ll each have as much to prove — and almost as much to lose — as in any debate in modern history. With the race resting on a razor thin margin and less than two months left in the campaign, any misstep could take on exaggerated importance. Both candidates, though, also need to confront their weaknesses — Trump needs to do his best to cut into Harris’ historic lead with female voters, while Harris must complete her introduction to the American public. A New York Times poll published on Sunday that had Trump and Harris virtually tied nationally (and sent Democrats into a minor panic) showed that 31 percent of respondents said they need to learn more about Harris, compared to only 12 percent who would like to learn more about Trump. That suggests her range of outcomes is larger than Trump’s — a strong debate could expand her support, while a weak performance could halt her momentum in its tracks. It’s been four years since her last debate, when she performed well against former Vice President Mike Pence (with the help of a well placed fly). Prior to that, Harris participated in five debates across the 2020 Democratic primary — her most successful and memorable moment of her disappointing showing came when she attacked her future boss President Joe Biden on the issue of school busing. But she’s never gone up against Trump head to head and her carefully managed press schedule to date has heightened concerns about her readiness for Trump’s onslaught. For Trump, tonight marks his second debate of the presidential campaign but it might be his only chance on stage with Harris. His June performance was barely discussed given how much Biden’s flailing on stage blotted out any other narrative. Now, Trump faces a rival close to 20 years younger in a race that’s a virtual dead heat. He’s tasked with more than simply protecting a polling lead. Harris will aim to bait Trump into a personal, ugly confrontation — a possibility that even Trump’s Republican allies fear. He gets into more trouble when he reflexively and relentlessly attacks — in their first 2020 debate, Biden notched his most memorable moment when he asked Trump “will you shut up, man” after his constant interruptions. Yet Trump also has a preternatural ability to throw his opponents off their gameplan with his wild and unfounded claims and the force of his personal attacks. There’s probably no more fitting venue for a political spectacle of this magnitude. In the two decades since the National Constitution Center opened its doors, it’s proved to be much more than just a temple to one of our founding documents. It’s been the scene of numerous presidential campaign town halls, election rallies and debates. It’s the site where during the 2008 primary season Barack Obama delivered his famed “A More Perfect Union” speech — better known as his “speech on race” — and it’s the stage President Joe Biden turned to in 2021 to defend the integrity of the 2020 presidential election, where he called the fight against restrictive voting laws the “most significant test of our democracy since the Civil War.” As a campaign backdrop, you’d be hard-pressed to find one more dramatic than Philadelphia. It’s not just the birthplace of American democracy, it’s the biggest city in the most important state of the 2024 election — with 19 electoral votes, Pennsylvania is the largest prize among the seven swing states. The winner of Pennsylvania is likely the next occupant of the White House. Philadelphia has played a uniquely adversarial role during the Trump era. Trump has openly expressed his disdain for Philly, framing the Democratic stronghold as a bottomless pit of electoral fraud. As far back as his first debate with Joe Biden in 2020, Trump tossed out a falsehood about poll watchers being blocked from observing the first day of in-person early voting in Philadelphia. “Bad things happen in Philadelphia, bad things,” he said. Earlier this summer, Trump took a different tack, characterizing the city instead as a place “ravaged by bloodshed and crime.” His animus toward the city is rooted in the political complexion of Pennsylvania. Trump’s considerable support is concentrated in central and western Pennsylvania. The City of Brotherly Love and its populous suburbs, however, anchor the southeastern corner of the state — the region that has twice delivered big margins against Trump, enough to wipe out his advantage in the rest of the state. Philadelphia served as home to the Biden campaign’s headquarters in 2020, and also the locus of some of the lowest moments in Trump’s failed reelection campaign. With the world watching, city election officials painstakingly counted the final votes that put Biden over the top in Pennsylvania, delivering the crowning blow to Trump’s defeat. That moment was followed by a press conference that will live in infamy — you may remember it from the Philadelphia parking lot where it was held, Four Seasons Total Landscaping. Recognizing the space Philadelphia occupies in Trump’s head, in advance of the debate mysterious counterfeit ads appeared on bus shelters across the city last week claiming that Harris had been endorsed by the Philadelphia Eagles — creating a flap that forced the team to disavow the ads and clarify that they were not sanctioned by the NFL franchise that the city obsesses over. It wasn’t the first time the Birds were caught in the MAGA crossfire. In 2018, Trump publicly rescinded an invitation to host the then-Super Bowl champion Eagles at the White House because so many players declined to attend. Then, two years later, it was Rudy Giuliani’s turn to disparage the city. At a press conference disputing the election results, Giuliani singled out Philadelphia as a particularly “corrupt city,” one where election fraud is “as frequent as getting beaten up at a Philadelphia Eagles football game.” Welcome to POLITICO Nightly. Reach out with news, tips and ideas at nightly@politico.com. Or contact tonight’s authors at cmahtesian@politico.com and cmchugh@politico.com or on X (formerly known as Twitter) at @PoliticoCharlie or @calder_mchugh.
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