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MICHAEL WOLFF: Why Trump’s top aides tell me they’re now holding their breath – as he ignores their advice and makes one final risky gamble to break this historic election deadlock

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Last week, I asked a top Trump official whether he would be placing a bet on the outcome of the election.’I’m not betting,’ came the reply.I asked the same question of a major Democratic Party donor (far richer than the Trump aide).Their response? ‘I’ll contribute whatever it takes for Kamala to win. But a bet? An actual bet? That’s a different story.’We’re now deep into ‘silly season’ in American politics – during which, as the election draws near, any serious politico or pundit is expected to have a definite view on which way the vote will fall. And yet, very few people I speak to – at any level of expertise or insider standing – are making such an out-front call.With less than four weeks to go, this is the closest-fought presidential election in modern history. All the signs agree: advantage nobody. Last week, I asked a top Trump official whether he would be placing a bet on the outcome of the election. ‘I’m not betting,’ came the reply. With less than four weeks to go, this is the closest-fought presidential election in modern history. All the signs agree: advantage nobody. In a way, this is all part of the Great Political Humbling brought about by the emergence of Donald J. Trump.If you listened to the pollsters in 2016, Trump was a certain loser.In 2020, with Covid, and after four years of Trump chaos, the smart money reasonably counted Trump out. But then he pulled within 44,000 votes of winning – close enough for him, and many others, to dispute the results.Then, in a harsh rebuke, and despite predictions of a looming ‘Red Wave’, many of Trump’s Republican proxies were wiped out in the 2022 midterms.Except, months later, when Trump declared he would be running in 2024, he rose once again in presidential polls and, without hardly ever sacrificing his golf game, flicked away all his Republican challengers with near-effortless ease.What’s more, he’s managed to somehow sidestep every legal hurdle that threatened him along the way.Democrat confidence soon turned into a great foreboding – and it culminated, after the Trump-Biden debate, in such certainty of defeat that the Party ousted its old-man standard bearer, the sitting president.The emergence of Kamala Harris not only confused the race, but confused Trump himself, whose primary talking point had been Joe Biden’s weakness and fragility.The two-year race was suddenly reduced to little more than 90 days, making Trump’s usual strategy of repeating insults until they stick much less effective.But then, even with Harris’s early and meteoric stardom, she has since reverted to the stubborn mean, a relative dead-heat in the polls with Trump. And that’s where things have stayed since late August, with neither Harris’s worshipful convention, strong debate performance, nor anything else managing to move the needle.Steve Bannon, that key architect of Trump’s 2016 victory and perspicacious gadfly, once theorized to me that in close presidential elections – and, indeed, most of this century’s major elections worldwide – little matters except the final two weeks of a campaign and the last impression on the minds of swing voters.It’s all about the so-called ‘October Surprise’ or, at least, an unpredictable change in the autumn wind.And so here we are.Team Trump believes that Trump, the consummate salesman, always knows how to close a deal.In October 2016, he surrendered his phone, and hence his reckless tweets, to his son-in-law and chief advisor, Jared Kushner. His sudden discipline and focus on the grievances of working men and women in Michigan, Wisconsin and Pennsylvania helped bring him his electoral college victory.Likewise, in 2020, he finally hit his stride in late October, with a stronger than expected debate performance, tightening the race. Another week of that ‘on-message Trump’ might actually have swung it for him.A problem, however, with relying on Trump for that strong finish, is that the ‘final impression’ for voters comes down to his volatile mood swings and off-script impulses.Virtually all of Trump’s advisors have urged him to focus on the economy, undoubtedly the most significant issue in this year’s race.But instead, this October, Trump has doubled down on his personal resentment toward Harris – and on the anger he feels that his winning campaign against Biden was ‘stolen’.Even when he does focus on key policy issues in his rambling speeches, he tends to dispense with the economy, turning instead to immigration – the issue he believes won him 2016 and that will bring his supporters home again in 2024.But a byproduct here is that immigration tends to be an emotional hot-button for Trump, sending him careening into rage and often incoherence — not the ideal last impression.Still, his team, while holding its breath, also acknowledges that, in so many past instances, Trump’s ‘instincts’ have worked to his advantage.If he wins, Pennsylvania will likely have been crucial. And if so, his winning flush, the Trump camp is already theorizing, could well have been this past weekend’s ‘Return to Butler’ rally, the scene of the first assassination attempt against him in rural Pennsylvania.Coming back to Butler, recalling that extraordinary moment and focusing his considerable star power on this rural community, where a few thousand votes could hand him the election, was his own reality show brainstorm. If Trump wins, Pennsylvania will likely have been crucial. And if so, his winning flush, the Trump camp is already theorizing, could well have been this past weekend’s ‘Return to Butler’ rally.It is, however, confounding to Team Trump – which has long equated ‘winning’ the news cycle with winning – that the Harris campaign has seemed to shy away from headlines, notably going quiet after the great excitement of the Democratic convention and after her certain debate victory in September.Instead of dominating the news, Harris’s strategy appears to have been to stay measured, tempered and – in the few interviews she has granted – careful to avoid big headlines.Her past week of higher-profile media hits — Howard Stern, 60 Minutes, The View, the podcast ‘Call Her Daddy’ — can then be read in two very different ways: that she is comfortable enough with her lead (the latest New York Times/Siena poll has her 3-points ahead, though yet neck-and-neck in the swing states) to risk greater exposure – or that she is panicking, having suddenly decided she must dramatically change her media strategy.In many ways, both campaigns continue to feel that the other side will be key to victory: Donald Trump and the deep aversion felt by so many Americans is the Democrats’ favored hand; and Kamala Harris and the visceral dislike, and deep suspicion, of her in MAGA-land is the Trumpers’ ace.In the usual dramatic arc of a presidential campaign, such politics of personality are worked out in a final TV debate. But this time, leaving everyone hanging, there won’t be another debate head-to-head – no last look in this election.This historic deadlock may continue to hold. Without an ‘October Surprise’, and with neither side ready to fold, that could mean November, December and January surprises.

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