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Trump’s Professional Missteps Outshine Harris’ Unlikely Success

Former President Trump found himself undeniably on the losing side of Tuesday night’s debate, widening the financial chasm between himself and VP Kamala Harris, who bizarrely seems to be in favor with donors of all sizes for the eighth consecutive week. Trump’s inability to capitalize on this pivotal event has left key donors and fundraising activists disillusioned and skeptical. Once drunk on the intoxicating overconfidence of the Republican National Convention, elite Trump enthusiasts are now confronting the harsh reality of being crushingly outspent.

A debate, a formative event essential to both high- and low-dollar fundraising, turned into a near disaster as Trump supporters openly voiced dismay over unbefitting debate moderation. Their criticism, while squarely in line with Trump’s own accusations of bias, was also tainted with disappointment in Trump’s handling of the situation. Many believed that regardless of perceived unfairness, Trump shouldn’t have let the evening dissolve into a lost battle.

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The debate, watched with growing concern by prominent Texas fundraiser Doug Deason and his billionaire father, Darwin Deason, turned into a painful spectacle. Deason Senior expressed discontent over Harris and his growing frustration with Trump’s haphazard performance. “Trump just cannot properly discuss policy,” Mr. Deason said, an alarming critique from a long-time associate. He pointed out that Trump had countless opportunities to counter Harris’s questionable claims, but he unfortunately seemed to have failed more often than not.

Keith Rabois, a venture capitalist, and another hefty contributor to pro-Trump causes shared similar sentiments. Friends and acquaintances flooded him with anxious messages expressing concerns over Trump’s performance during the debate. That the debate ended on a strong closing statement, as per Rabois’s opinion, did little to assuage the nagging concern that Trump hadn’t seized significant opportunities to decisively undermine Harris. Many worried that this was far from Trump’s finest hour.

Trump’s vague promises of a comeback seem to rest heavily on Senator JD Vance of Ohio, Trump’s running mate. Rabois is hosting a fundraiser for Vance and is expecting to raise more than $1 million for their campaign. But the question remains whether Vance’s careful execution of anti-Harris debate strategy can overhaul the twisted perception created by Trump’s erratic performance. Only time will answer that.

The world’s wealthiest individual, Elon Musk, who has shown substantial support for Trump, oddly rejoiced in Harris’ performance, which he claimed exceeded most people’s expectations. He did nothing to shield Trump’s lackluster performance from criticism. It seems even Trump’s staunchest financial backers are perplexed by his recent performance.

Trump’s puzzling display comes at a time when his campaign faces a severe financial crunch. After first experiencing funding issues in spring while contesting against President Biden, he passed Biden’s resources by June. However, ever since Harris usurped Biden at the head of the ticket, she’s been on an eight-week fundraising rollercoaster, nearly tripling Trump’s financial figures for August. The debate seems to have only energized her financial base, consisting of both magnates and smaller contributors.

Despite the troubling signs, the Trump campaign remains tight-lipped about its financial standing. The accumulating wealth has enabled Harris to craft a ubiquitous campaign strategy, spending three times as much as Trump’s campaign in July. It is evident from the massive advertising outlay ‘Harris & Co.’ have decided to commit. From now until election day, Harris aims to outrun team Trump on television and radio by a projected $131 million.

Trump’s campaign infrastructure is also considerably smaller than that of Harris. She boasts of over 2000 staffers coordinated with Democratic Party groups. The Trump campaign, on the other hand, largely bank on outsourcing their canvassing work to groups like Turning Point Action, the Faith & Freedom Coalition, and America PAC. This super PAC is expected to be financed mostly by Musk, who seems to be steering it successfully to allure major donors beyond its initial backers.

Even as this occurs, Trump has found it hard to expand his pool of financial supporters since his 2020 presidential run. High-flying Republican donors such as Ken Griffin, the CEO of Citadel who spent over $100 million on the 2022 midterm cycle, is yet to endorse Trump after backing former South Carolina Gov. Nikki Haley during the Republican primary. It looks like this might not change soon. As such, Trump has heavily relied on a select few donors who are keeping him barely relevant in the paid media space.

This group of donors includes billionaires Musk, Timothy Mellon, Miriam Adelson, and Ike Perlmutter, who are supposedly injecting hundreds of millions of dollars into supporting Trump’s campaign. Notwithstanding, the Republican movement is clearly underfinancial pressure, evidenced by Trump’s more frequent appearances at fundraisers to restore his dwindling resources, even in non-competitive states like Utah and California.

Meanwhile, the Vice President seems to be coasting comfortably without any planned finance events except one in Washington, arbitrary perhaps. It appears that the current situation permits her to delegate her fundraising events to popular figures, a luxury she can afford when she’s not as desperate for cash as she is for her time.

As the finish line approaches, grim shadows loom over the Republican financial landscape. Trump continues to travel extensively for fundraisers while Harris leisurely plans her strategies in the comfort of a seemingly unending fund inflow. The disconcerting contrast is evident and underscores the changing dynamics of this campaign.