During the course of planning, Wolkoff had corresponded with Ivanka about the cost of using the Trump Hotel for events leading up to the swearing-in ceremony. On December 10, 2016, a Trump Organization employee sent an estimate for a ballroom rental and food and beverage minimum to use the Trump Hotel space for eight days. The price she quoted was $3.6 million, according to an e-mail. A week later, Gates e-mailed Ivanka about the cost. In this exchange, first published this past December by ProPublica and WNYC, Wolkoff flagged her concern. “These events are in PE’s [the president-elect’s] honor at his hotel and one of them is for family and close friends. Please take into consideration that when this is audited it will become public knowledge,” she wrote. (Peter Mirijanian, a spokesperson for Ivanka’s counsel Abbe Lowell, said in a statement: “When contacted by someone working on the inauguration, Ms. Trump passed the inquiry on to a hotel official and said only that any resulting discussions should be at a ‘fair market rate.’ Ms. Trump was not involved in any additional discussions.”)

For an event producer used to detailed lists and punctilious itemization, Wolkoff was often caught off guard by the ad-hoc nature of the committee. According to the two people familiar with the matter, Gates approached a couple individuals working on the inauguration and asked if they would be willing to be paid directly for their work by a donor, rather than by the inaugural committee. They had received more donations than they’d initially anticipated, Gates told these people. Skirting the usual payment route could allow the inaugural committee to avoid reporting the full amount raised from donors. (A lawyer for Gates did not respond to a request for comment.)

Wolkoff frequently told Melania about her concerns regarding Gates, these people said. She relayed her concern about the high access level of his security pass within Trump Tower and his closeness with the Trump family. In her view, these people said, he exacerbated a situation already fraught with potential conflicts of interest. Members of the inaugural committee talked about how he frequently worked out of Donald Trump Jr.’s office. He was in constant communication with the adult children in order to keep them in the loop about decisions surrounding the inauguration.

Wolkoff also questioned Gates and Barrack about pricing and budgets across the board, according to the people familiar with the conversations. She started to grow concerned about being left out of meetings, particularly as she raised more red flags. Because part of her responsibilities included reviewing all budgets from her vendors and presenting them to other members of the inaugural committee, she studied the line items in order to be able to explain them. At points, she could not justify the numbers coming in. After circulation of a quote from one of their largest event-production vendors, Hargrove LLC, Wolkoff was shocked that no one in the organization appeared willing to question the figures. She suggested that the quote seemed far beyond what the Obama inaugural committee would have been charged in 2009. She sent an e-mail to her team and Barrack on December 31, 2016. “I am DISGUSTED by [Hargrove’s] lack of transparency and entitlement to [the Presidential Inaugural Committee’s] funding,” she wrote. “I can not approve any budget line items because I do not have a clue what these numbers represent!!” (Hargrove did not immediately respond to a request for comment.)

One of the most concerning aspects to Wolkoff’s team, according to the people familiar with the situation, was the amount of money and attention being spent on Barrack’s chairman dinner, which he hosted on an evening before the swearing-in. A draft guest list for the event from days before the dinner included the likes of retired Lieutenant General Mike Flynn, G.O.P. fund-raiser Elliott Broidy, Michael Cohen, and key officials in the incoming administration. Among the list marked as confirmed were seven people described as “foreign ministers” for Saudi Arabia, one foreign minister from Qatar, and one from the United Arab Emirates. They were the only people on the list who were unnamed. (On Tuesday, ProPublica published a memo that showed Barrack’s investment firm planned to profit from its connections to the Trump administration. A spokesperson called it “an outline of a proposed potential business plan which was never acted upon or implemented.”)