‘He should be doing better’: Even some Trump allies see him veering off course

Donald Trump was meeting privately in mid-September with one of his oldest friends, Steve Wynn, when the casino mogul and Republican mega-donor delivered the former president a blunt warning: You’re off message, and it isn’t helping.

Trump had been distracted, in Wynn’s view. The former president at the time was promoting a conspiracy theory that Haitian immigrants were eating people’s cats and dogs in Ohio, among other things. To drive home his point, Wynn showed Trump polling and suggested the former president would be better off focusing on policy issues where Republicans see his opponent, Kamala Harris, as vulnerable, according to two people briefed on the meeting and granted anonymity to describe it.

The meeting underscored a key point of tension inside the Trump campaign. While polls show the race is incredibly close, some of Trump’s allies are concerned that his impulses and coarse approach to campaigning are undermining him against Harris, a rival who has proved far stronger than his previous opponent, Joe Biden.

In interviews, more than a dozen Trump allies described the former president as reaching a crossroads — faced with the choice of continuing with the missteps that have overtaken the past several weeks of his campaign or embracing a more calculated approach aimed at appealing to a small subset of undecided voters who are likely to sway the outcome of the election. In recent weeks, he has brought into his fold destabilizing forces like social media provocateur Laura Loomer and his controversial former campaign manager Corey Lewandowski, plugged commemorative Trump coins, and asserted that if he loses, Jews would be partly to blame.

“It’s not that he’s going backwards,” said one Trump ally granted anonymity to speak freely. “But he should be doing better.”

Wynn, in a text message, said the description of the meeting was “inaccurate,” though he did not respond to further requests for comment.

For all the tumult of the last few months, Republicans are cautiously optimistic about Trump’s prospects. Public polling shows a close race in key battleground states that will determine the outcome. On Monday morning, a New York Times/Siena College poll showed signs of strength for Trump in Georgia and Arizona — two states Biden won in 2020 — and a slight lead in North Carolina.

The National Republican Senatorial Committee’s executive director, Jason Thielman, told donors at a retreat in Sea Island, Georgia, over the weekend that Trump was out-performing his poll numbers compared to similar points in the 2020 and 2016 election cycles, according to an attendee.

“It’s a close race but today President Trump would decisively win,” said John McLaughlin, a pollster for the Trump campaign. “Having worked for Trump in 2016 and 2020 we’re in a better position than we were in past elections.”

Still, with the race entering its final stretch, there is concern about Trump within the party’s top ranks. The former president had steamrolled his Republican primary opponents and established a stable lead over Biden. But over the past several months — one of the most turbulent periods in American political history, in which Trump was targeted in two apparent assassination attempts and Biden withdrew from the race — Trump has veered off course.

Some allies said that after opening a lead on Biden, and with a return to the White House seemingly close, the reality of now facing a tougher opponent in Harris has been disorienting to the former president. He has repeatedly expressed anger in private over the Biden-to-Harris switch.

In response, Trump has returned to his comfort zone of lightning-rod associates, conspiracy theories and vitriol and has opened the door to outside voices who embrace a more freewheeling approach. In mid-August, Trump told his advisers he wanted to bring in Lewandowski, who in 2021 had been removed from a top position in a pro-Trump super PAC after he was accused by the wife of a donor of making unwanted sexual advances toward her at a charity dinner in Las Vegas.

But Lewandowski, the year after Trump took office, had also co-authored a book entitled “Let Trump be Trump.” Lewandowski has done little to push back on Trump’s impulses, according to one person familiar with the dynamic.

The move has proven to be disruptive for an operation that until that point had been the most functional of Trump’s three presidential campaigns. According to three people briefed on the discussions, Trump had said privately he wanted to get Lewandowski involved as a surrogate. But since joining, they said, Lewandowski has begun to refer to himself as the campaign’s chair while trying to exert control over the campaign’s operations — roles that he had not been given.

As Trump began preparing for the Sept. 10 debate, he worked with his team to develop “pivots” — lines that could be used to turn a question into a more favored topic. Those familiar with the preparations, which included Florida Rep. Matt Gaetz and former Hawaii Rep. Tulsi Gabbard, said the sessions went well. But when Trump took the stage at the National Constitution Center in Philadelphia, Trump was thrown off balance by Harris’ efforts to get under his skin, especially her assertion that his supporters were bailing on his rallies. Many of the pivots did not end up being employed.

Also problematic was that Trump undercut his efforts to attack Harris on immigration — a centerpiece of his campaign and an area where polling shows Harris is vulnerable — by baselessly asserting that Haitian immigrants in Springfield, Ohio were eating residents' pets. According to two people briefed on the discussions, Trump was aware of the story by coverage in The Federalist, a conservative outlet that published a 911 call from a local resident. Ohio Sen. JD Vance , Trump’s running mate, had also been promoting the story.

“Trump is strongest when he is talking about what people care about the most: the economy, immigration, crime, trade, the Trump core messages,” said Republican strategist David Urban, who ran Trump’s successful 2016 campaign in Pennsylvania, a state that could decide the 2024 election. “When he gets distracted and goes in different directions, it's less helpful. Every day we're not talking about those issues, we're letting Harris go untouched.”

While some Trump aides have said Trump’s ongoing focus on the conspiracy theory has helped the former president by bringing immigration to the fore, others privately conceded that the pet-eating storyline and the former president’s overall combative tone was a missed opportunity to attack Harris. Last week, Ohio Gov. Mike DeWine penned an op-ed in which he criticized Trump and Vance over their ongoing fixation with Springfield, where life has since been upended by the claims.

The next day Trump had a new problem on his hands: Loomer.

Trump has long viewed the bomb-throwing activist as, in the words of one ally, a “fighter” — one of his highest compliments. Shortly before the debate, Trump invited her to fly with him to Philadelphia. The decision proved to be problematic, more so since Loomer also traveled with him the following day to events commemorating the anniversary of 9/11. Critics — some of them Republicans — pounced on the association, given that Loomer had once called 9/11 an “inside job.”

The fallout surrounding Loomer didn’t stop there. After she posted on X racist and offensive cultural stereotypes about Harris and her Indian American identity, Georgia Rep. Marjorie Taylor Greene , a staunch Trump ally, blasted Loomer for what she called her “appalling and extremely racist” rhetoric. Loomer fired back with a post of her own in which she went after Greene. The firestorm would only intensify the following day, when North Carolina Sen. Thom Tillis and South Carolina Sen. Lindsey Graham joined Greene in condemning Loomer.

Trump was behind the scenes fielding calls from allies worried about Loomer’s presence, leading him to finally distance himself from her. On Sept. 13, Trump wrote on X that Loomer “doesn’t work for the Campaign,” and that he “disagree[s] with the statements she made.”

But then on Sept. 15, Trump surprised Republicans again when he weighed in on the recent endorsement of Harris by one of the world’s most popular young female pop stars.

“I HATE TAYLOR SWIFT!” Trump posted to Truth Social.

One ally speculated that Trump’s all-caps message on a Sunday morning was in response to a poll about Swift’s impact on the race that had just been shown on ABC News’ “This Week.” Trump had privately been irritated by the endorsement and decided to put Swift — who is a native of the must-win state of Pennsylvania — on blast to his millions of followers.

And Trump wasn’t done with his freewheeling approach. Four days later, when he traveled to Washington to appear at back-to-back events focused on combating antisemitism, he said that Jewish voters “would have a lot to do with the loss ” if he does not win in November and said that the Senate majority leader, Chuck Schumer , who is Jewish, was “Hamas all the way.”

In a statement, Trump campaign spokesperson Steven Cheung said Trump “has built the most powerful and most professional team in political history and, under his leadership, has overcome every single obstacle in his way.”

Loomer declined to comment, while Lewandowski referred comment to the campaign.

It is unclear how much Trump’s comportment will shift the election. After nearly a decade in the spotlight, many top Republicans say voters simply have made up their minds about the former president — either they like him or they don’t, and there’s not much that can sway them.

"Chins are going to wag no matter what happens, especially this at this point in the campaign,” said Urban. “Everyone is a campaign strategist.”

Still, several Trump allies have expressed concern about his rhetoric — and about a former president who has for several weeks appeared to be off track when the race is incredibly close.

One Republican National Committee person said: “You need to avoid distractions as you're building momentum towards Election Day.”

Lisa Kashinsky contributed to this report.