President Donald Trump’s allies are worried that the most damaging of the many recent departures from his White House may be that of Keith Schiller, a little-known former bodyguard who’s one of the President’s closest confidants outside his family.

Schiller is leaving the White House soon to return to the private security business, according to three people familiar with his plans, for a job that will pay far more than his $165,000 government salary. His title, director of Oval Office operations, hardly begins to describe his importance to Trump, who is “crushed” by his planned departure, according to one person close to the President.

Multiple people interviewed described Schiller as an emotional anchor for the President in a White House often marked by turmoil. Schiller has worked for Trump for nearly two decades, and within the West Wing he serves as the President’s protector, gate-keeper and wing man, according to people close to Schiller and Trump. Most of the people requested anonymity to candidly discuss relationships between the President and his aides.

“He’s a confidant and friend,” said Stuart Jolly, a former national field director for Trump’s presidential campaign. Trump “trusts Keith, and Keith trusts him. Trust is a really big deal at that level.”

​Schiller has also acted as Trump’s hatchet-man. It was Schiller who told James Comey that the President had decided to fire him as FBI director. Two weeks ago, after Trump was angered by preparations for a rally in Phoenix, Schiller delivered the message to another longtime aide, George Gigicos, that Trump no longer wanted him to organise such events, according to three people familiar with the matter.

Schiller declined to comment.

Schiller never planned to stay in the position for long because of its lower pay and longer hours, according to two people who know him. But his exit may have been accelerated by the appointment in July of retired Marine general John Kelly as Trump’s Chief of Staff. Since taking the job, Kelly has sought to tighten access to the Oval Office, control information flowing to the President and instal a more formal regime within the White House.

Schiller has told friends that working under Kelly is very different, and that he doesn’t like the job as much. He has said he believes that Kelly doesn’t like Trump personally and is serving as chief of staff predominantly out of a sense of duty to country, according to three people familiar with his views. That has been deeply demoralising for Schiller, who is accustomed to Trump being surrounded by devoted employees, two people said.

​Schiller lost his privilege to walk into the Oval Office at any time when Kelly took over. And he now views his job as somewhat redundant, people close to him said. The President has Secret Service to protect him, valets to fetch what he needs, aides to dial his phone — people to handle every facet of Oval Office operations.

Two people close to Trump said they worry that Schiller’s departure will leave the President and the West Wing off-balance, given the deep relationship the two men share. These people said that Schiller’s exit could put Trump on a collision course with Kelly, who does not understand as well how Trump likes to operate.

Trump’s allies may have more personal concerns. Schiller is a contact for Trump friends who want to reach the President. And campaign staffers knew the best way to get Trump’s ear was to slip a note to Schiller — especially if they wanted to bypass Trump’s first campaign manager, Corey Lewandowski, whom Schiller didn’t always get along with.

On many days, Schiller is the first and last aide Trump sees. During the campaign, Schiller heard nearly every conversation and phone call as he sat in cars by Trump’s side, travelling between rallies, former campaign aides said.

Schiller served in the Navy and as a New York City police officer before becoming a part-time body guard for Trump in 1999. He was named head of security for the Trump Organization in 2004. He knows most employees at the company and shares his opinion of all staffers, inside and outside the White House, with the President.

Discontent among Trump friends and allies outside the White House has grown as Kelly has sought to streamline and professionalise the Oval Office. The new Chief of Staff has imposed new protocols for getting face time or ideas in front of the President — cutting off a cadre of trusted regulars whose advice and conversation Trump relished.

Doors in the building that were once open are now literally closed, including those leading from the West Wing lobby and anterooms and halls to the Oval Office, serving as a symbol of the more limited access to Trump.

“It was like a fraternity house the first six months and now it’s a military compound — it’s a fort,” one former aide said.

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Schiller doesn’t entirely disagree with Kelly’s changes, one ally said. And Trump has remarked that a more regimented schedule has provided him time to think, read and reflect, a White House official said.

Once Schiller leaves, the only comparable loyalists remaining in the West Wing will be Trump’s daughter Ivanka Trump, son-in-law Jared Kushner, communications aide Hope Hicks, and digital aide Dan Scavino. But none currently fills the role of peer and friend that Schiller holds.