CNN  — 

President Donald Trump’s relationship with his chief of staff John Kelly was beyond repair when he announced last December that Kelly would be stepping down.

So before Kelly could leave, Trump asked the retired four-star general the question that often consumes him when a top aide leaves his side on bad terms: Did he plan to write a tell-all book about his time in the White House?

Kelly assured Trump in one of their final Oval Office meetings that while he did plan to eventually write about his tumultuous tenure in the White House for history’s sake, he wouldn’t publish a book until after Trump was gone, two sources briefed on the conversation said. But the former general’s guarantee came in terms more reminiscent of a military ceasefire than an employee separation agreement: Kelly told Trump he would hold his fire as long as Trump didn’t attack him first.

A source close to Kelly said the exchange was amicable and not contentious. Neither Kelly nor the White House responded to CNN’s request for comment.

Eight months later, the non-aggression pact has largely held up, but the stream of jilted aides filtering out of the White House has not abated. Now Trump is facing the departure of yet another official whose proximity to power and messy departure brings the threat of a damning tell-all account.

The abrupt exit of Madeleine Westerhout, who sat outside the Oval Office for two-and-a-half years as executive assistant to the President until last week, once again sent Trump and his advisers into damage control mode as book agents and publishers began circling the waters, floating a possible six- or seven-figure book advance.

“While Madeleine Westerhout has a fully enforceable confidentiality agreement, she is a very good person and I don’t think there would ever be a reason to use it,” Trump tweeted. “She called me yesterday to apologize, had a bad night. I fully understood and forgave her!”

But Trump, who was fuming after reports that Westerhout had bad-mouthed him and his family, only accepted the phone call and apology after several aides encouraged him to allow Westerhout to make amends, a senior Trump adviser said.

“Do we really want her as an enemy? No, we don’t,” the adviser said.

Soft landings

Trump aides said an effort was now underway to find a soft landing for Westerhout, who also served as director of Oval Office operations. It was not yet clear where she would land, but the effort fit a pattern by White House officials, campaign aides and others in Trump’s orbit to ensure that senior White House officials and others close to the President are taken care of after they leave the building.

However, one former administration official marveled at how poorly the Trump White House handles the ouster of employees by firing and embarrassing them before trying to find them a cushy job on the outside. The official said in other administrations an employee who could be a liability was kept in the fold by moving them into another attractive role in the administration to prevent unseemly disclosures.

Trump’s first director of Oval Office operations, Trump’s longtime bodyguard Keith Schiller, and his personal aide John McEntee, quickly found their way onto the Republican National Committee and Trump campaign payrolls, respectively.

Omarosa Manigault-Newman was offered a job on the Trump campaign after her messy departure from the White House in what she described as an attempt to buy her silence.

“It sounds a little like, obviously, that there are some things you’ve got in the back pocket to pull out,” Trump’s daughter-in-law Lara Trump, a senior adviser on the campaign, told Manigault-Newman in a recorded phone call Manigault-Newman later released. “I think we can work something out where we keep you right along those lines.”

Former White House deputy chief of staff for communications Bill Shine was announced as a senior adviser to the Trump campaign after his sudden resignation, to the surprise of most campaign officials. Several aides said they have not spotted him at the campaign’s Virginia headquarters.

Legal threats

But if soft landings and fence-mendings are the carrots employed by Trump and his aides, non-disclosure agreements and the threat of Trump’s wrath are the stick.

The dual strategy is evident in the second half of Trump’s two-part tweet on Westerhout, where he warned that he is “currently suing various people for violating their confidentiality agreements.”

None of those lawsuits, though, have been successful and most legal experts believe that the non-disclosure agreements that Trump has forced dozens of White House officials to sign are unenforceable because they are government employees.

Trump pushed his first White House counsel to come up with a “souped up NDA” that would bar White House staffers from dishing on him and his family, but former White House counsel Don McGahn pushed back, warning Trump that the agreement would not be enforceable, a source familiar with the matter said.

The White House Counsel’s Office ultimately authored a more diluted version of the NDA Trump had hoped for, focusing more on confidential national security information, which the source called “semi-enforceable.”

Trump has long used non-disclosure agreements in his business and private life before becoming president, which sources said stem from Trump’s longstanding paranoia about people gaining access to his inner circle only to betray him by inking books that would undercut the self-image he has long sought to portray to the public.

Twitter fire

Beyond the threat of lawsuits, Trump aides looking to tell all must also prepare to incur Trump’s wrath on Twitter, where he frequently attacks and disparages his critics.

When former White House aide Cliff Sims’ book was published, Trump slammed him as “a low level staffer” and “gofer” who “wrote another boring book based on made up stories and fiction.” Sims is now suing Trump in his official capacity as President for attempting to “silence” him.

Trump aides’ attention has now turned to other projects by former top officials.

Former Defense Secretary Jim Mattis’ book initially was not a cause for concern at the White House, but White House aides now believe that Trump will start going after Mattis – who is promoting the book – for his veiled criticism of Trump.

Former White House national security adviser H.R. McMaster, former UN Ambassador Nikki Haley and former director of the National Economic Council Gary Cohn also both have books in the works, sources said. Aides view those as potentially more damaging than Mattis’, since at least two of them worked inside the White House at some of its more chaotic moments and frequently clashed with Trump.

It’s not clear if any of them are prepared to divulge the inner workings of Trump’s West Wing, but they all witnessed some of the most turbulent moments of Trump’s presidency, which Trump would consider embarrassing and a breach of loyalty. But one source familiar with the matter said their books are more policy focused for now and that they’ll likely wait until after the election to share more about their time in the White House.

CORRECTION: This story has been updated to accurately reflect the White House roles of Keith Schiller and John McEntee.