Trump long has relied on nondisclosure deals to prevent criticism. That strategy may be unraveling.

Now, in one of the most sweeping efforts by a former associate to undo nondisclosure agreements, the Trump campaign’s former Hispanic outreach director last week filed her latest effort in a class-action suit to void all such campaign contracts. She says they are so broad that they deny individuals their First Amendment right to say anything critical of the president — even as he routinely takes to Twitter to mock and deride his critics.

In a motion for summary judgment in the case, the former campaign worker, Jessica Denson, said the campaign sought a $1.5 million claim against her for violating an NDA. She said that came after she filed a lawsuit alleging sex discrimination by campaign officials. (That separate case is ongoing.)

“These NDAs are representative of the levers of fear that this campaign and administration wield over people,” Denson told The Washington Post. “And if this lever of these NDAs is lifted, it is significant not only for the direct effect it has on people who have signed it, but for a general environment of people who are afraid to speak out.”

Under her agreement, Denson was not allowed to disparage Trump during her time with the campaign “and at all times thereafter,” and she cannot disclose whatever “Mr. Trump insists remain private or confidential,” as defined by him.

Denson’s attorney, David Bowles, said that he and his legal colleagues hope to win the case before Election Day, enabling hundreds of people who may have signed similar agreements to have the contracts voided and emboldening them to speak out about Trump.

“You can’t stop people from criticizing political candidates,” Bowles said. “It is the heart of the Constitution and free speech.”

The Trump campaign has battled Denson for more than two years and paid nearly $1 million to a law firm involved in the case, according to federal election records, although it is not clear how much is related to the lawsuit or other legal advice. A representative of the firm, LaRocca Hornik Rosen & Greenberg, did not respond to a request for comment. The Trump campaign also did not respond to a request for comment.

In its response to Denson’s request for summary judgment, Trump’s legal team said that Denson’s lawsuit is an effort to get out of a “standard business confidentiality agreement” and that the agreement has not stopped Denson from criticizing Trump.

The case is just one of several legal battles in which the campaign or the Justice Department is seeking either to penalize people it says have violated NDAs or to prevent future disclosures. The NDAs typically are part of a private employment contract, and thus it is unknown how many people have signed them directly with Trump, his company, his campaign or other entities with which he is allied.

Trump’s family tried to stop the publication this summer of a tell-all book by his niece Mary Trump. President Trump told Axios that his niece was “not allowed” to write the book, and his lawyer Charles Harder filed briefs on behalf of Trump’s younger brother, Robert, in an effort to block it. Robert Trump said in court papers that Mary Trump was prohibited from publishing such a memoir because she signed a confidentiality agreement in a 2001 inheritance case. Harder did not respond to a request for comment.

Mary Trump said in an interview that she hoped her willingness to speak out against President Trump would encourage people who signed various NDAs to tell their stories.

Donald Trump has long used NDAs, Mary Trump said, as a means of wielding “his power, his position and his money and his apparently endless supply of lawyers to run out the clock. Or just to outspend people who can’t afford it. And I think it’s absolutely being used as a weapon to advance his own agenda.” She said anyone running for president should be required to void any NDAs so that they can be fully vetted.

Her lawyer said the willingness of law firms such as his to defend those who signed confidentiality agreements could be a turning point in encouraging people to speak out.

“Individuals who signed NDAs have seen that there are lawyers and organizations who will come out and protect them and defend their First Amendment rights, and therefore they are less fearful of coming forward and speaking about issues of public concern,” said Theodore Boutrous Jr., who has worked for free for the past two years for Mary Trump.

Earlier this summer, President Trump’s Justice Department tried to stop the publication of a book by his former national security adviser John Bolton, who was subject to an agreement with the federal government not to disclose classified information but did not sign an NDA with Trump.

The government’s lawyers asked a court to block publication, but a federal judge ruled that the book had already leaked and thus the effort was moot.

Last week, the Justice Department filed court papers saying Bolton “never received written authorization” that a review for classified information had been completed, and the government sought to seize Bolton’s earnings from the book. The Justice Department said that Bolton “has been unjustly and materially enriched — to the tune of $2 million dollars — by information he had no right to release.”

Trump appears to have instituted his practice of requiring NDAs shortly after one of his former casino executives, Jack O’Donnell, published an explosive 1991 book titled “Trumped!,” which exposed failings in Trump’s personal and business lives. In a 2016 interview with The Post, Trump said he believed O’Donnell had signed an NDA and promised to provide a copy to a reporter, but he never followed up. O’Donnell said he never signed such a document.

“I know for a fact that shortly after it became public that my book was coming out, he began making all employees at the casino sign NDAs,” O’Donnell said.

Around the same time that O’Donnell’s book was published, Trump divorced his first wife, Ivana. Trump’s lawyer Jay Goldberg said in an interview that he instituted a clause in the settlement that forbade Ivana Trump to disclose details or speak negatively about her former spouse.

Ivana Trump said in a brief telephone conversation, “I don’t talk about my ex-husband.”

During the 2016 campaign, adult-film actress Stormy Daniels signed an NDA in exchange for a $130,000 payment, a deal arranged by Michael Cohen, who was then Donald Trump’s personal attorney. Trump at one point said he knew nothing about the agreement, which The Post’s Fact Checker declared was “a lie.” Cohen later said in court that he was reimbursed by the Trump Organization for the payment to Daniels and that Trump knew about it.

Trump was so enamored of NDAs that, as he sought the presidency four years ago, he told The Post that he planned to require anyone who worked for him in the White House to sign similar agreements.

“When people are chosen by a man to go into government at high levels and then they leave government and they write a book about a man and say a lot of things that were really guarded and personal, I don’t like that,” he said.

Several versions of an NDA for White House officials were drafted, including one that imposed a $10 million penalty, The Post has reported. But, unlike in the campaign, where everyone was expected to sign such a contract, it is not clear how many people agreed to them in the White House, especially after the early days of the administration.

When Trump would bring up the issue, top aides told him that NDAs wouldn’t be viable in the federal government, which already imposed restrictions on the release of classified information, according to a former senior White House official.

The former White House official, speaking on the condition of anonymity to discuss internal deliberations, said that Trump “talked about nondisclosure statements all the time. He would talk about the power of these NDAs in the civilian world. He never could quite adjust to the fact that he couldn’t terrorize people with these NDAs.” The official said he never signed one and did not know anyone who did.

The White House did not respond to a request for comment.

Mark Zaid, a Washington lawyer who offered to represent for free anyone who signed an NDA in the White House and now wants to void it, said no one has taken him up on the offer. But in those cases in which a former White House official had previously signed an NDA with the campaign or a Trump-related business, the campaign sometimes has taken legal action against them.

For example, when Cliff Sims, former White House director of message strategy, wrote a book called “Team of Vipers,” Trump tweeted that Sims was “a low level staffer” who “signed a non-disclosure agreement. He is a mess!”

The campaign filed an arbitration claim against Sims for violating his NDA. In turn, Sims sued Trump to void the NDA, arguing that he wrote about information he learned as a federal official. Sims’s lawyer was Zaid, who said a settlement was reached that he is not allowed to discuss. Sims did not respond to a request for comment.

One of the bitterest cases revolved around the 2018 publication of a book by Omarosa Manigault Newman, a former contestant on Trump’s reality television show who was director of African American outreach in the campaign and a communications official at the White House. After resigning from her government job, Manigault Newman published her book, “Unhinged,” which described the president as a racist and said that “his mental decline could not be denied.”

In response, Trump tweeted that “Wacky Omarosa already has a fully signed Non-Disclosure Agreement!” and that she was a “dog” and a “crazed, crying lowlife.”

The Trump campaign then sued Manigault Newman for allegedly violating an NDA, which includes a non-disparagement clause.

Manigault Newman’s attorney, John M. Phillips of Jacksonville, Fla., said the campaign lawsuit is designed “to tie up Omarosa” and send a message to anyone who signed an NDA and is considering whether to speak out against the president. He said his firm has done legal work for Manigault Newman worth $750,000, underscoring the difficulty faced by anyone in a similar position.

Phillips noted that Trump tweeted that he is responsible for suing people who he says violated their agreements. “Yes, I am currently suing various people for violating their confidentiality agreements,” Trump tweeted in August 2019. “Disgusting and foul mouthed Omarosa is one.”

Phillips said that is an admission by the president that “this is his lawsuit and they need it washed through the campaign.” Phillips said Trump’s comment opened him to being deposed in the case.

The campaign lawsuit was filed by Trump’s attorney Harder, who is involved in several nondisclosure cases. Federal election records show that the campaign has paid Harder’s firm at least $3.1 million, although they don’t say how much of that is related to the Manigault Newman case.

In an arbitration hearing on the case, Harder said that even if Trump “misspoke and was referring to the campaign,” the president is “not a party to this case” and should not be subject to a deposition.

The next battle over a book is likely to center on Cohen, Trump’s former personal attorney. He is writing a book about Trump that is slated to be published in September.

In his February 2019 testimony before Congress, Cohen agreed with a congressman’s assertion that Trump used NDAs “to prevent people from coming forward with wrongdoing.”

Cohen’s book is tentatively titled “Disloyal: The True Story of Michael Cohen, Former Personal Attorney to President Donald J. Trump.” He has said it “will contain my first-hand experiences and observations based on my decade-long employment and relationship with Mr. Trump and his family, both before and after he was elected President of the United States.”

Trump’s attorney Harder sent Cohen a letter warning that such a book would violate Cohen’s NDA with Trump, Cohen said in court papers. But Cohen could have the last word. He said, “I do not believe that I ever signed such an NDA.” 

Alice Crites contributed to this report.