In late summer 2017, after eight months at the White House with Trump, Schiller was ready to move to Florida, make more money and get outside the Beltway, according to former White House aides. Inside the West Wing, Schiller also reportedly chafed under the newly imposed, top-down leadership style of then-chief of staff Gen. John Kelly.
At the same time, on Capitol Hill, the Republican National Committee was coming under pressure from Trump allies who wanted it to use its specially designated legal fund to help pay personal attorney fees for the president and his eldest son, Donald Jr., who were caught up in the early stages of the special counsel's Russia probe.
As former Trump campaign aide Michael Caputo told CNN at the time, "I think it's a responsibility of everyone in the Republican Party to take care of the president and his family first. They didn't sign up for this bogus investigation and it's our responsibility to protect him as much as we can."
The RNC agreed to tap the fund. In August and September 2017, it spent more than $427,000 on lawyers for both men. But an uproar ensued when the RNC later reported the payments on its mandatory monthly campaign filings.
Even within the RNC, many staffers reportedly believed that the legal fund, originally created to pay for things like vote recounts, was never intended to pay anyone's personal legal bills related to a criminal proceeding.
The last legal bill the committee paid for the Trumps was on Sept. 18, 2017, for Don Jr. Yet within days, the RNC quietly started paying three other Trump-related expenses, according to committee filings with the Federal Election Commission.
The first was a salary for John Pence, nephew of Vice President Mike Pence, who was earning around $12,000 a month from Trump's re-election campaign.
Next came $37,500 a month in rent payable to the Trump Organization for office space in Trump Tower, which was used by the president's re-election campaign.
Schiller officially left his job at the White House on Sept. 20. But unlike McEntee, he did not immediately return to the Trump campaign, where his most recent job outside of government had been. Instead, he landed at the RNC.
On October 4, 2017, one week after the Trump Tower rent payments started, the RNC cut its first check for $15,000 to Schiller's KS Global Group for what it called "security services."
The expense was disclosed by the committee on its next campaign filing in October, as required by law. But it went unnoticed by reporters for another three months.
One month after he was retained by the RNC, Schiller sat for an interview with the House Intelligence Committee, which had launched its own investigation of Russian meddling in the 2016 election.
There, on November 7, 2017, Schiller reportedly denied a salacious allegation that Trump interacted with prostitutes during a 2013 trip to Moscow, on which Schiller had accompanied him.
At the time of Schiller's testimony, records show that KS Global Group had already collected $30,000 in fees from the RNC. Schiller had also moved to Boca Raton, Florida, full time, according to Florida state corporation filings. One week before he testified on Capitol Hill, Schiller had registered KS Global Group in Florida, and listed his home address as an apartment in Boca Raton.
The RNC wasn't the only pro-Trump group helping Schiller to make ends meet, however. Also not yet reported at the time was the fact that Schiller's lawyers were being paid, at least in part, by the Trump campaign. Between January and April 2018, the campaign paid more than $94,500 to Schiller's attorney's law firm, according to campaign finance reports.