News that Kimberly Guilfoyle contracted the coronavirus had barely surfaced on July 3 before she hopped on a private flight from Mount Rushmore back to New York with her boyfriend, Donald Trump, Jr.
Left behind in her wake after President Donald Trump’s pre-Independence Day address were more than a half-dozen junior campaign staffers whom Guilfoyle oversees as the president’s national finance chair. The aides, who’d been in proximity to Guilfoyle, were forced to quarantine in their Rapid City, S.D., hotel rooms for three days and barred from face-to-face contact with colleagues as they pleaded with the campaign to get them home.
The campaign tried to reassure the staffers, checking in with them and stressing the need to wait a few days to take a coronavirus test. But the aides felt deserted and scared they’d get sick in a city they’d never set foot in before. They were so distraught that weeks later they sought out Stephanie Alexander, the campaign’s chief of staff, to vent about the experience, according to people familiar with the incident.
The episode was the latest example of upheaval within the fundraising unit that Guilfoyle oversees, which is primarily responsible for cultivating networks of donors who cut checks in increments up to $2,800. Interviews with nearly a dozen Republicans familiar with the campaign’s fundraising depict an operation beset by departures, staffers with no prior fundraising experience and accusations of irresponsible spending.
Trump is raking in big money online and has amassed an enormous war chest. But Joe Biden has outraised the president for two consecutive months, and there are growing concerns among senior Republicans about whether the dysfunction within Guilfoyle’s team is translating into money left on the table for what has become an uphill fight for a second term.
Her staff is in upheaval. Last week, several of them requested a meeting with then-campaign manager Brad Parscale to air their grievances. The sit-down never took place — Parscale lost his job before it could happen — but they did meet with Alexander. They described a feeling of confusion and said it felt like they were caught between the competing demands of longtime fundraiser Caroline Wren and Guilfoyle confidant Sergio Gor, who oversee the unit’s day-to-day operations.
Finance staffers privately complain about a pressure-cooker environment in which employees are berated when they’re perceived to not be measuring up. They compare working under Wren and Gor to living with two warring parents; some Republicans argue that staff discontent is less about Guilfoyle than about the pair working directly under her.
The team has seen three full-time staffers leave the past two months, including two with past fundraising experience. The most recent departure came earlier this month. Each transferred to different positions within the campaign after finding the culture of the finance operation untenable.
Particularly concerning to some Republicans is that a few of the new additions have not worked as political fundraisers before. One is a friend of Gor and the child of Don Huffines, a major GOP donor. Another is New York socialite and Guilfoyle friend Somers Farkas. People close to the operation acknowledge that Farkas was an unorthodox hire but pointed out that she had spent years raising money for an array of causes.
There are growing Republican worries that the internal turmoil will hurt the campaign’s fundraising. The task of shepherding midlevel donors demands a high level of organization and staff coordination, with outreach to thousands of people who are neither megadonors with bottomless bank accounts nor smaller contributors being hit up for a few hundred dollars at most.
Those involved with the campaign describe the 51-year-old Guilfoyle, who took on the finance chair role in February, as one of the president’s most tenacious fundraisers. The former Fox News host has taken on the challenging task of developing a traditional donor network, something George W. Bush made famous with his “Pioneer” program, but which the anti-establishment Trump has struggled to create. Her supporters say she has performed in the face of a pandemic that has chilled the fundraising environment by cutting off most in-person donor events.
Campaign officials said the bundling program had raised around $73 million and that she had grown the network from roughly 1,000 in January to 6,500.
Guilfoyle’s unit is part of a massive Trump fundraising apparatus. Her department raises money into Trump Victory, a joint account between the reelection campaign and the Republican National Committee. While Guilfoyle’s team is mainly responsible for gathering $2,800 checks, the committee focuses on collecting donations into the hundreds of thousands of dollars. There is also the Trump Make America Great Again Committee, which vacuums up small-dollar contributions.
“Kimberly is one of the president’s strongest and hardest-working advocates, and he is lucky to have her fighting in his corner,” said Ronna McDaniel, the RNC chair.
House Minority Leader Kevin McCarthy said, “When it comes to raising valuable resources and connecting with voters, Kimberly Guilfoyle is putting on a master class.”
But Guilfoyle has rankled fellow finance staffers by claiming what they consider to be her reluctance to share credit for successes. Trump this week hosted a “virtual” fundraiser that drew $20 million largely from small-dollar donors who gave online, an operation Guilfoyle doesn’t oversee day to day. Guilfoyle hosted the event and interviewed Trump during the broadcast. But in the days after, aides expressed annoyance about a press release issued afterward that quoted Guilfoyle but made no mention of anyone else who helped organize the effort.
While establishing a bundling network was always going to be difficult for Trump after his frontal assault on the party establishment, people involved in the campaign say there’s still an imperative for any incumbent president to maximize donations across the board — and a recognition that, with Biden well ahead in polls, every cent will count.
Some remain irked by a recent pro-Israel-themed Zoom fundraiser. The campaign signed off on plans for tickets to the event, which coincided with the anniversary of Trump’s decision to move the U.S. Embassy from Tel Aviv to Jerusalem, to be made available to donors for $1,000. But Guilfoyle’s team then began circulating tickets to some donors for $150, leading to confusion.
People familiar with Guilfoyle’s decision say she wanted the fundraiser to be a lower-cost grassroots event, allowing more people to participate. But others expressed concern that the event raised less money than it could have and worried about the perception that some donors were asked to pay more than others to participate.
There are also questions about spending. In March, two staffers chose not to fly commercial and instead took the private jet of a major Trump donor to the president’s Mar-a-Lago resort for a finance event. The campaign had to reimburse the roughly $25,000 cost.
Trump campaign officials were galled when they realized they’d be footing the bill for the flight. Staffers on the reelection effort are typically expected to book travel on an internal office database and use low-cost commercial flights.
Guilfoyle herself has used private planes to travel to and from fundraisers. But people close to her argued that it amounted to a small sum given that the events often net millions of dollars. The logistics of traveling to multiple fundraisers in such a short amount of time, they added, often make commercial travel unrealistic.
Those close to Guilfoyle say that while her style isn’t for everyone, she is well liked by her staff.
In response to inquiries for this story, the campaign provided statements from finance team members who lavished praise on Guilfoyle. Maggie Mulvaney, director of finance operations, said the group is “united behind Kimberly Guilfoyle’s leadership. We are a team and we have a singular purpose of victory for President Trump.”
CORRECTION: An earlier version of this story misstated the city Guilfoyle flew back to from Mt. Rushmore.