Trump has notched a list of once-unthinkable ‘firsts.’ Will they prevent him from winning?

Former President Trump stands on the verge of a series of firsts that once would have seemed unthinkable.

Winning a second term as president would make the Republican nominee the first occupant of the White House to be: a convicted felon, an adjudicated sexual offender, a twice-impeached federal office holder and a serial denier of election results that have been certified by the courts and Congress.

Trump has not only weathered those largely self-inflicted wounds, but persuaded somewhere approaching half of Americans to consider putting him back in the White House. For a significant share of Trump supporters it is his opponent, Vice President Kamala Harris, who is too extreme to lead the country.

Many Harris supporters express incredulity that Trump remains a viable candidate. But veteran political analysts said that, for mostly apolitical voters who don’t follow the news closely and who may decide the election, Trump’s repeated departures from political norms may have little practical effect on their daily lives.

The analysts say it is incumbent on Harris to use the closing days of the campaign to explain why Trump’s past failures should matter to them.

“I think for her it is about saying that this is a guy who brings chaos, who is unhinged, who is too out of control,” said Patrick Toomey, a partner in BSG, a Democrat-aligned polling firm. “With that and his crazy vendettas and penchant for retribution, will he ever be focused on delivering help for average Americans?”

A longtime Republican pollster agreed. Greg Strimple of GS Strategy Group said the best possible messengers to make that case to the small group of moderate and wavering voters are the phalanx of Republicans and former Trump administration officials who say Trump is unfit for office.

Former Secretary of Defense Mark Esper, former national security advisor John Bolton, former White House Chief of Staff John F. Kelly and Gen. Mark Milley — the former chair of the Joint Chiefs of Staff — are just a few of a large cadre of those who served during the Trump administration who have since signaled that they believe he is not fit to serve a second term. No other president in modern history has provoked so many high-level defections.

Strimple said those once handpicked by the former president to help him lead the country can deliver a powerful closing argument against Trump: “We saw it from the inside,” they can say. “And it’s worse than you think.”

“Trump right now is doing what he needs to do to be successful, and that’s making it an issues referendum on the last four years of Biden-Harris,” Strimple said. “She really needs to find a pivot to get this back onto a referendum [about] character and the leadership style of Donald Trump.”

The list is long of politicians who foundered after a single misstatement or damning personal revelation. Texas Gov. Rick Perry’s bid for the presidency disintegrated in 2011 after he froze on a debate stage when asked to name the three federal departments he had pledged to eliminate.

Trump’s misstatements became so frequent, and his insistence on spurning corrections so adamant, that much of the U.S. media pushed back harder. It became common for Trump not just to be accused of being wrong, but of intentionally lying.

By the time he left the White House in 2021, the Washington Post had cataloged 30,573 Trump falsehoods during his four years in office. That amounted to 21 erroneous claims a day — what the newspaper called a “tsunami of untruths.”

But Trump not only has transcended the fact-checking, he has turned his battles with the mainstream media, academics and other experts into a cudgel: Only he dared stand up to elites, who he contended did not understand, or care about, average Americans.

His most ardent followers see each ensuing condemnation from the media and the courts not as proof of guilt but as a continuation of a “witch hunt” against their hero. Evangelicals look past personal shortcomings because Trump delivered on his promise to overturn the abortion rights protected in Roe vs. Wade. Business leaders focus on tax cuts and deregulation. Working class Americans remember that prices were lower when Trump was president.

A partial list of some of Trump’s impolitic and scandalous moments and how he responded:

34 felony convictions

• In May, a New York jury found Trump guilty of 34 felony counts, involving his part in a cover-up of hush money payments to keep former adult film star Stormy Daniels from going public about having sex with him.

Trump is scheduled to be sentenced on Nov. 21. He continues to appeal, charging, among other things, that politics motivated prosecutors.

Jan. 6: Impeached and indicted

• On Jan. 6, 2021, having lost his November election against Biden, Trump urged his followers to march to the U.S. Capitol and “fight” as Congress voted to certify the result. His loyalists stormed the Capitol, injuring about 140 police officers, while he watched on TV. It took three hours before Trump said in a Rose Garden video that his followers should “go home now.”

Trump has repeatedly said he did nothing wrong because he told the crowd to march “peacefully and patriotically.” He recently reframed the melee as “a day of love.” But in his hourlong speech on Jan. 6, he invoked the word “fight,” or variations, 20 times, saying at one point: “We fight like hell and if you don’t fight like hell, you’re not going to have a country anymore.”

The House voted to impeach Trump for inciting the insurrection, but the Senate acquitted him of the charges, allowing him to remain in office.

Special counsel Jack Smith led a federal investigation that resulted in Trump being charged with taking part in a scheme to interfere with the peaceful transfer of power. The prosecutor is trying to keep the case alive by showing that many of Trump’s actions fall outside so-called official acts that the U.S. Supreme Court has said should be immune from prosecution.

Trump and his running mate, Sen. JD Vance (R-Ohio), continue to claim that Trump won in 2020 — a claim that dozens of courts and reviews have rejected.

Georgia election interference charges

• In early 2021, as Congress prepared to certify former Vice President Joe Biden’s victory over then-President Trump, he called Georgia Secretary of State Brad Raffensperger, making various claims about ballots being “shredded” and his supporters being denied a chance to vote. Without offering proof of widespread abuses, Trump insisted: “I just want to find 11,780 votes. I need 11,000 votes, give me a break.”

More than two years later, a grand jury in Fulton County, Ga., indicted Trump on charges of racketeering and other crimes, saying the former president had conspired to change the outcome of the 2020 election while participating in a “criminal enterprise.”

A judge later threw out some of the counts against Trump, saying prosecutors failed to provide enough detail about the underlying felony he was accused of committing. Trump contends the prosecution amounted to retaliation by a Democratic prosecutor, Fulton County Dist. Atty. Fani Willis. The case remains unresolved, in part because of the former president’s efforts to disqualify Willis.

Classified documents case

• In June 2023, a special counsel filed dozens of felony counts against Trump, accusing him of illegally hoarding classified documents from his time in the White House. Special counsel Smith contended that Trump kept the documents at his Mar-a-Lago estate in Palm Beach, Fla., and then obstructed the FBI when federal agents tried to get the records back.

He pleaded not guilty and denied doing anything wrong. A federal judge appointed by Trump dismissed the case in July, saying that Smith had been improperly appointed by Atty. Gen. Merrick Garland instead of being confirmed by Congress.

Found liable for sexual abuse

• In May 2023, a New York jury found Trump liable for sexually abusing advice columnist E. Jean Carroll in 1996. She won a $5-million judgment. Earlier this year, a jury awarded an additional $83.3 million after concluding that the former president continued to defame Carroll on social media.

Trump’s lawyers have tried to have the verdicts thrown out, contending the trial court allowed jurors to hear improper and inflammatory evidence.

Ukraine and the first impeachment

• In 2019, Trump called Ukrainian President Volodymyr Zelensky and suggested his government should launch an investigation into former Vice President Biden, his Democratic opponent, and Biden’s son Hunter. The request came at the same time that Trump was withholding crucial military aid to the struggling U.S. ally.

The Democratic-controlled House of Representatives impeached Trump for abuse of power and obstruction of Congress for what House prosecutors said was Trump’s attempt to strong-arm the Ukrainians.

Trump said the House’s investigation and impeachment amounted to “three years of sinister witch hunts, hoaxes, scams,” with Democrats “trying to nullify the ballots of tens of millions of patriotic Americans.” He was acquitted by the Senate.

A $355-million fraud judgment

• In February of this year, a judge ordered the former president to pay $355 million, plus interest, after concluding that Trump lied for years about his wealth on financial statements. Those documents were used to obtain loans to support his real estate empire.

Appellate court judges signaled last month that they may have sympathy for some of Trump’s arguments. They noted that none of the companies he did business with suffered financial harm and questioned whether the trial judge awarded too large a judgment.

Each time the media and other observers have predicted Trump had crossed a threshold he couldn’t survive, he has proved otherwise. It’s a pattern that has been repeated throughout Trump’s life: He has moved ahead, despite reports of marital infidelity, multiple business failures, half a dozen bankruptcies and the airing of a video in which he boasted that he could grab women “by the pussy.”

Trump’s odd behavior lands the same way. He makes speeches with long and sometimes nonsensical digressions. Just in recent days, he stopped a Q&A session near Philadelphia when a couple of people fainted, instead playing music for the crowd for more than half an hour while he swayed along on stage. He used a four-letter word to describe his opponent, Harris. And he ended a long digression about Arnold Palmer with a vulgar aside about the golf great’s anatomy.

But even some who describe themselves as exhausted with Trump’s misbehavior say they are more focused on other things. The two issues mentioned most commonly: Inflation and illegal immigration.

“All of these [Trump failures] should matter. But common-sense arguments, arguments that worked in the past have stopped working,” said Strimple, who recently has completed polling for the Cook Political Report. “Right now, Trump has successfully made it a referendum on the Biden-Harris administration.”

Strimple agreed with Toomey, the Democratic pollster, that Harris needs to put the focus back on Trump’s most outlandish statements and actions.

But to truly be the “change” candidate that she needs to be, Harris also must make much clearer how her presidency would be different from that of Biden, whom she has served with for four years, said Strimple, and Steve Schmidt, a one-time Republican political strategist and ardent Trump opponent.

Harris did serious damage to that effort when she went on “The View” this month and said that “not a thing that comes to mind” when she was asked if there was anything that she would have done differently from President Biden over the last four years, Schmidt said on his podcast, “The Warning.”

Harris later has said she would appoint a Republican to her Cabinet and focus on housing and small business in new ways, trying to distinguish herself from Biden.

But Schmidt urged her to do even more to make her independence clear.

“What people want to know is what she will do differently from Biden,” Schmidt said. “Unless and until you cross that bridge, you’re going to fall short on election day.”