WASHINGTON — Kimberly Guilfoyle’s popularity with major donors caught the attention of President Trump last year, as she traveled the country appearing at fund-raisers for his re-election campaign with her boyfriend, Donald Trump Jr.
Ms. Guilfoyle, a former Fox News host, had been hired by the campaign as a senior adviser, but in December, the president personally asked her to lead the fund-raising effort of Trump Victory, his campaign’s main committee for major donors.
She accepted, and was tasked with developing a network of mid-tier supporters who are seen as pivotal to Mr. Trump’s chances of winning a second term, and with whom he never formed a deep bond in 2016.
Ms. Guilfoyle made inroads with some of the donors who had rejected calls from others on Mr. Trump’s team. Yet Trump supporters inside and outside the campaign now say the operation she has built hasn’t lived up to the expectations of some Trump fund-raisers, and that her management style and that of some of her aides have alienated others.
Some of the problems have been attributed to the inability to conduct in-person fund-raising since the coronavirus pandemic began shutting down Mr. Trump’s donor events in March. Midlevel donors tend to give more when they can see and speak with the president.
But in interviews with The New York Times, Ms. Guilfoyle’s critics said that she had devoted a disproportionate amount of attention to glitzier, high-dollar fund-raising, and that they believed she used her position — and the fact that she’s seen as a de facto member of the Trump family — to support her public image and lifestyle. Most of those interviewed insisted on anonymity because they were not authorized to discuss the issue publicly.
“I think she likes the spotlight a little too much,” said Dan Eberhart, an oil executive and a donor to Mr. Trump. He called Ms. Guilfoyle a voluble supporter of the president, but said that when she was previously working for the pro-Trump super PAC America First Action, she often talked about her own media presence.
At least two staff members asked to be taken off her team, in part because they disliked working with other members, according to people familiar with the circumstances behind moves. And a lavish birthday party for Ms. Guilfoyle at Mr. Trump’s Palm Beach club in March was partly funded by some campaign donors, which raised eyebrows.
More concerning to some donors and campaign aides has been private plane use by Ms. Guilfoyle and her team, which has caught the eye of several staff members. In January, as requests started coming in for private flights, the campaign had to work out a plan for approving such trips, which must be listed as in-kind contributions or reimbursed by the campaign in order to comply with campaign finance laws.
Ms. Guilfoyle’s private flights did not violate those laws, although in one case, two of her aides, without seeking prior approval, took a private flight to a fund-raising event in March. The campaign then had to reimburse for the trip at a cost of tens of thousands of dollars, according to two people familiar with the trip.
Tim Murtaugh, a campaign spokesman, said that flights categorized as in-kind contributions to the campaign are funded by the donors directly. Aides said such planes had allowed for maximum attendance by top officials at multiple events per day. “In any event,” Mr. Murtaugh said, “the cost of flights and the efficiencies they provide are investments in fund-raising events that raise millions of dollars for the president’s re-election.”
Through the campaign, Ms. Guilfoyle declined to be interviewed. The Trump campaign provided statements praising Ms. Guilfoyle and the campaign’s fund-raising effort from the Republican National Committee’s chairwoman, Ronna McDaniel; Jeff Miller, a veteran Republican fund-raiser; Representative Kevin McCarthy of California, the House Republican leader; and two members of the finance team.
Ms. McDaniel called Ms. Guilfoyle one of Mr. Trump’s “strongest and hardest-working advocates.”
The complaints about Ms. Guilfoyle’s fund-raising numbers reflect some of the harsh realities of Mr. Trump’s re-election prospects, particularly in the era of the coronavirus. A businessman who trusts almost no one, Mr. Trump has often turned to a small circle of family and friends for critical aspects of his re-election, regardless of their previous experience. That is what happened with Ms. Guilfoyle, people familiar with the situation said.
And his campaign’s fund-raising, once seen as an overwhelming advantage, has lagged in the last two months behind that of his Democratic opponent, Joseph R. Biden Jr.
The mid-tier donors that Ms. Guilfoyle has been tasked with developing are seen by campaign insiders as a key to closing the fund-raising gap. These donors give their own money, but also are dispatched to collect — or “bundle” — potentially significant sums from their associates.
Mr. Trump’s untraditional 2016 campaign did not have an organized program devoted to bundling, which requires endless rounds of phone calls; it is usually left to lower-profile finance staff and consultants, rather than big-name campaign surrogates with close ties to the Oval Office like Ms. Guilfoyle, the ex-wife of Gov. Gavin Newsom of California, a Democrat.
Ms. Guilfoyle left Fox News in 2018 and took a position at America First Action. That year, she and the president’s son revealed they were a couple.
At fund-raising events, donors responded to her Fox News celebrity and would line up to meet her, according to America First aides. But they said Ms. Guilfoyle was mostly used as a surrogate and did not have any staff reporting to her. They said she left the super PAC to maintain a legally mandated firewall between it and the campaign, which often deployed the younger Mr. Trump as a surrogate.
At the campaign, she initially served as a senior adviser when it was run by Brad Parscale, before accepting the title of national chair of the Trump Victory finance committee. Mr. Parscale has paid Ms. Guilfoyle since she came to the campaign, routing the payments through his private company.
Ms. Guilfoyle’s defenders say that she is being targeted by junior staff members on the campaign who don’t like what they view as her blunt style. They say she works nearly around the clock, sometimes making calls past midnight to lock in donations.
“Kimberly has amazing energy and brought a lot of new people into the campaign and made them feel empowered and important,” said Jack Oliver, a veteran Republican fund-raiser. “Her relationship with the family makes people understand that the president cares about the work the volunteers are doing.”
Her defenders also say she has made the best of a tricky situation, throwing herself into virtual donor cultivation, participating in bundler conference calls and phone banks, and presiding over an increase in activity by some donors and bundlers, despite having scaled-back activity because of the coronavirus.
They insist her deputies, Caroline Wren, a veteran Republican fund-raiser, and Sergio Gor, a former aide to Senator Rand Paul, Republican of Kentucky, are effective.
Still, under Ms. Guilfoyle’s stewardship, mid-tier donors have not contributed as much as hoped by some Trump allies involved in fund-raising for Trump Victory, which comprises Mr. Trump’s campaign committee and the R.N.C.
Bundling figures are fungible and, with the exception of the amounts bundled by lobbyists, which are subject to mandatory disclosure to the Federal Election Commission, there is no way to fact check them. The people critical of Ms. Guilfoyle said the tallies attributed to her initiatives are sometimes padded to make them appear more successful. Sometimes bundlers are retroactively credited as having raised funds that were not initially attributed to them, they said.
The campaign said that the funds credited to the bundling program were tracked using identification numbers affiliated with individual supporters.
The Trump campaign said it raised more than $20 million this week from a virtual fund-raiser organized by Ms. Guilfoyle. But according to internal tallies, more than half of those funds came from small donors who paid $45 or more to participate, while $6 million came from major donors who were treated to a video chat with Mr. Trump that was moderated by Ms. Guilfoyle.
That means less than $4 million came from donors who gave in the middle-tier of roughly $2,800 each, the category Ms. Guilfoyle is responsible for, despite the fact that donors in that range were offered access to a separate program featuring appearances by top Republican officials.
Overall, the campaign said that the bundler program accounted for $73 million of the $91 million raised by Trump Victory since the beginning of this year, though there is no way to independently corroborate this figure. And it said that since Ms. Guilfoyle took the helm of the program in mid-January, it increased the ranks of bundlers from 1,000 to 6,500.
After Ms. Guilfoyle tested positive for the coronavirus during a trip to Mount Rushmore for an official White House event celebrating the Fourth of July, people close to her said that she and Donald Trump Jr. would drive back to the East Coast.
But they flew aboard a private flight instead, leaving behind Trump Victory aides to Ms. Guilfoyle, who were told to self-quarantine in their hotel for several days, according to a Politico report on Thursday.
A campaign aide said that it was not Ms. Guilfoyle, but other campaign officials, who had instructed the staff to remain in South Dakota, and that the change in her plans came because it was deemed less of a security risk than driving across the country with Mr. Trump’s son, who requires Secret Service protection.
Annie Karni contributed reporting from Washington.