Some Trump Allies Believe He is Veering Off Course

In mid-September, Donald Trump held a private meeting with his long-time ally, Steve Wynn. During their discussion, Wynn, a prominent casino owner and Republican donor, issued a straightforward critique. He told Trump that he was “off message,” suggesting that his recent antics were not benefitting his campaign.

Wynn’s concern stemmed from Trump’s focus on conspiracy theories involving Haitian immigrants, such as bizarre claims about them attacking pets in Ohio. To steer Trump in a more favorable direction, Wynn shared polling data indicating that the former president should pivot towards policy matters where his opponent, Kamala Harris, might be more vulnerable. This meeting highlighted a growing concern among Trump’s supporters, who worry that his erratic campaigning style could jeopardize their chances in an election that is shaping up to be very tight.

More than a dozen individuals close to Trump have noted that he finds himself at a critical juncture. He can either continue down a path filled with missteps or adopt a more calculated strategy to appeal to undecided voters, who are expected to play a pivotal role on Election Day. Lately, Trump has associated with controversial figures such as Laura Loomer and Corey Lewandowski, engaged in promoting collectible Trump coins, and made inflammatory comments, including blaming Jewish voters should he lose.

“It’s not that he’s going backwards,” remarked one ally, who chose to remain anonymous, “but he should be doing better.” Wynn, however, disputed the characterization of their meeting but did not provide further details when asked.

Despite the chaos of recent months, Republicans have begun to express cautious optimism regarding Trump’s election prospects. Ongoing public polls reveal a neck-and-neck race, especially in crucial battleground states that will ultimately decide the outcome. A recent New York Times/Siena College survey indicated promising signs for Trump in previously Democratic-leaning Georgia and Arizona, as well as a slight advantage in North Carolina.

Jason Thielman, executive director of the National Republican Senatorial Committee, informed party donors at a retreat that Trump is currently performing better than he was at this stage during the 2020 and 2016 election cycles. Pollster John McLaughlin, who has previously worked with Trump, echoed this sentiment, asserting that the former president is in a stronger position than in past elections.

Nevertheless, as the campaign enters its final phases, some high-ranking Republicans express unease about Trump. After securing a firm lead among primary contenders and distancing himself from Biden, the emergence of Harris as a formidable opponent has thrown the former president off balance. He has conveyed frustration over the shift from Biden to Harris in private discussions.

In response to this pressure, Trump appears to have reverted to a more chaotic style dominated by conspiracy theories and inflammatory remarks. He sought to bring in figures like Lewandowski, despite past controversies that led to his temporary removal from a pro-Trump super PAC. With Lewandowski’s arrival, his influence has caused some operational disruptions within what had been a well-organized campaign.

As Trump prepared for a debate on September 10, his team attempted to formulate message “pivots” to redirect difficult questions to his preferred topics. The debate preparations included prominent figures such as Congressman Matt Gaetz and former Congresswoman Tulsi Gabbard, and they reportedly went well. However, upon taking the stage, Trump struggled to maintain his focus, particularly when Harris attempted to provoke him with remarks about his diminishing rally attendance.

Trump weakened his own platform on immigration, a critical issue that polls show Harris has vulnerability on, through ill-advised comments regarding Haitians allegedly harming pets. This narrative, which his followers amplified, detracted from a chance to compromise on key issues that resonate with voters.

Republican strategist David Urban stated, “Trump is at his best when discussing what matters most to the electorate: the economy, immigration, crime, and trade. When he veers off course, he does himself a disservice. If we’re not addressing these issues daily, we allow Harris to go unchecked.”

While some Trump aides argue that focusing on the conspiracy theory has kept immigration in public discussion, others admit that the pet-eating story resulted in a missed opportunity to critique Harris effectively. Ohio’s Governor Mike DeWine recently wrote an op-ed that criticized both Trump and Vance for their obsession with the Springfield claims.

The day after the debate, Trump faced more backlash due to his association with Loomer, whom he had invited on his campaign plane. Loomer’s participation became contentious, particularly given her past remarks regarding sensitive topics. After she made offensive comments about Harris’s Indian heritage on social media, even staunch supporters like Rep. Marjorie Taylor Greene condemned her statements, leading to a string of criticisms from several allies.

Amidst the mounting pressure from his circle regarding Loomer’s presence, Trump took to social media to distance himself from her, asserting that she “doesn’t work for the Campaign” and expressing disagreement with her views. However, soon after, Trump surprised many by posting a vitriolic message aimed at pop star Taylor Swift, reflecting his frustration with her endorsement of Harris.

Trump continued his freewheeling style by addressing Jewish voters during a recent event in Washington, stating they would bear some responsibility if he loses while making inflammatory remarks about Senate Majority Leader Chuck Schumer.

The Trump campaign maintains that it is built on a strong foundation. A spokesperson asserted that under Trump’s leadership, they have overcome numerous challenges. Observers remain divided on whether Trump’s recent behavior will significantly shift voter sentiment, as many believe opinions on him are already well-established.

“At this point in the campaign, everyone is busy suggesting strategies,” remarked Urban. While some Republican National Committee representatives cautioned against distractions, others worry that Trump’s erratic conduct could derail momentum as Election Day approaches.

Source: Rebecca Droke/AP