Mr. Freedman, Mr. Kupperman, Ms. Tinsley and another associate, Garrett Marquis, were affiliated with a Bolton-chaired nonprofit group, the Foundation for American Security and Freedom, which aired ads in 2015 opposing the Iran nuclear deal, from which Mr. Trump withdrew last week.
Ms. Tinsley, Mr. Marquis and Christine Samuelian, a longtime assistant to Mr. Bolton who has joined him as an aide at the N.S.C., also helped run a pair of political action committees fronted by Mr. Bolton that have raised more than $24 million since 2013 — including $5 million from the hedge fund magnate Robert Mercer — to support hawkish candidates.
Campaign finance reports filed Sunday show that the committees paid nearly $16,000 in payroll to Ms. Tinsley, who first worked with Mr. Bolton at the United States Agency for International Development, and nearly $8,700 to Ms. Samuelian last month after Mr. Bolton assumed his office at the N.S.C., though the PACs had already largely suspended operations and the payments were likely postdated.
Mr. Bolton also is close to the Republican megadonor Sheldon Adelson, an influential hawk and supporter of Israel from whom Mr. Bolton has sought assistance for his political ventures. Mr. Adelson, a casino billionaire, urged the Trump administration to hire Mr. Bolton for a senior post, according to someone familiar with the relationship, and also urged Mr. Trump to withdraw from the Iran deal. The day after Mr. Trump announced he was doing just that, Mr. Adelson attended a private meeting at the White House with Mr. Trump, Vice President Mike Pence, Treasury Secretary Steven Mnuchin and Mr. Bolton, though someone familiar with the meeting said it had been long planned and was unrelated to the announcement.
After Mr. Bolton was named national security adviser, Ms. Tinsley worked with him to wind down the political groups, while Mr. Marquis, a communications consultant who is a partner in a firm that has lobbied on behalf of foreign companies and one country, Japan, helped Mr. Bolton with public relations, reaching out to reporters to push back on critical stories and social media posts.
Mr. Marquis, 35, and Ms. Tinsley, 64, declined to comment. So did Mr. Freedman, Mr. Fleitz, 56, a former chief of staff to Mr. Bolton when he was under secretary for arms control in President George W. Bush’s administration, and Mr. Wurmser, 56, who served as a special assistant to Mr. Bolton in the Bush State Department and also as an aide to former Vice President Dick Cheney.
Mr. Palladino stressed that the overwhelming majority of N.S.C. staff are career government employees detailed from the military, foreign service, Civil Service and intelligence agencies, and he said there has been relatively little turnover in those positions.