The President was so furious at the situation, multiple sources told CNN, that chief of staff John Kelly was forced to navigate between two men who are, at this point, fed up with each other.
Kelly suggested to the President in a nuanced way that if Secretary of State Rex Tillerson left, the retired general's own ability to do his job properly could be at risk, sources familiar with the conversation said.
The discussion between the President and his top aide came as whispers about how long Kelly is going to last are getting louder.
"Every day for John Kelly ends in 'why?' Every day is tense," a source close to the President said, referring to the struggles Kelly faces.
The White House did not respond to a CNN request to comment.
This week's West Wing drama starred Tillerson -- one of Kelly's chief allies within the administration -- who found himself Wednesday on national television publicly proclaiming his loyalty to Trump after reportedly calling him a "moron" in private.
Kelly himself was not pleased when tensions between Trump and Tillerson became public. According to one source with knowledge of the matter, he let it be known "respectfully" that the President needed to "pull back" from his venting about his top diplomat and heed his advice to cool it. They all needed to cool it. Nobody was leaving, except the President to Las Vegas.
Instead of himself going to Las Vegas as he had planned, Kelly stayed behind to "manage" the Tillerson situation and try to control the fallout, according to multiple sources.
In the game of revolving senior aides and Cabinet members that has become Trump's White House, a new question has emerged: How long will Kelly last?
At Friday's White House briefing, press secretary Sarah Sanders was asked for the first time whether the President still has confidence in Kelly.
Her answer was an unequivocal yes. But the retired general who was brought in to control the daily White House chaos has recently found himself drawn into the very turmoil he was hired to quash.
"Theres no question there's friction in how Kelly approaches how the White House should run and how Trump approaches it," said Leon Panetta, White House chief of staff to President Bill Clinton and former defense secretary who worked closely with Kelly during his time at the Pentagon. "It does make sense to me that John Kelly would try to prevent additional disruption from occurring."
When Kelly was brought into the White House to take over for former chief of staff Reince Priebus, headlines blared that Kelly would impose military-style order on a chaotic Trump administration.
He closed the President's open-door Oval Office policy, curated his reading, and limited calls from his longtime outside friends with whom he loves to shoot the breeze. He was organizing, streamlining, controlling.
Since the retired general took the reins, the President has stirred a series of controversies: he rattled the world by warning of "fire and fury" against North Korea; said "both sides are to blame" in violence that included white supremacists; lashed out in a series of tweets at a fellow Republican, Senate Majority Leader Mitch McConnell, in personal terms for failing to repeal Obamacare; seized on and stoked the NFL controversy surrounding black players protesting during the National Anthem; and tweeted a video of himself knocking over Hillary Clinton with a golf ball.
Departures this summer of chief strategist Steve Bannon and short-lived communications director Anthony Scaramucci had Kelly's imprimatur, to be sure, but also had the blessing of a powerful family member whom some inside the White House liken as the real chief of staff: Jared Kushner, the President's son-in-law and senior aide.
When Kelly does get public credit for moves like removing problematic aides from the West Wing, or exerting hierarchical control over underlines, it sometimes doesn't go over well with the boss.
"When he gets credit for being the master, Trump doesn't like that," said one source close to the President. "Trump doesn't like being handed a script."
One person close to the President described the Kelly-Trump dynamic as "formal" as the two men continue to test each other's "trust barriers."
The relationship differs, this source says, from the one Trump had with Priebus, who Trump saw as someone he could control and liked on a personal level even though he never fully trusted him because of his ties to the Republican National Committee.
Some say Kelly's efforts have produced few examples of real change -- and few admirers in the White House. Trump himself sometimes points to the executive orders he enacted during the early days of his administration -- without Kelly in charge -- as evidence of his pre-Kelly productivity, according to a person familiar with the situation.
Kelly has plenty of supporters in Washington
Despite some internal criticism about a President whom some consider now too walled-off, Kelly has earned praise from Capitol Hill to the Cabinet for that very style.
"Reince was more reactionary," said a House Republican, who added the President's activities have taken on a more cogent theme and direction.
"But it's a tough job," the source said. "You're not going to change the President."
Trump finds ways to still talk to his friends, despite Kelly's attempts at limitations. One of those friends tells CNN the President has praised Kelly for bringing "discipline to chaos."
And though it is Trump's opinion that matters most, those who know him well know the President has varying opinions and gives differing descriptions of people depending on the day.
Kelly, says another source close to the President, is not the man in charge.
"Kelly's like the janitor," this source says harshly. "He's just the latest guy brought in to clean up."
This source predicts a tenure that lasts months, not years.
Those who know him say Kelly is intent on ensuring the West Wing can operate in a functional manner, even if the President himself hampers matters.
"I think John Kelly is hoping that he can try to protect the people that are rational in their job and at least have some sense of what the good policy is for the country," Panetta said.