J.J. Rendón stands on the balcony of his penthouse in Miami, where he met with a Post reporter on April 10. ( Emma Brown/The Washington Post)

Shortly after she first contemplated selling her story of an affair with Donald Trump, former Playboy model Karen McDougal sought advice from a curious source: a political operative who has helped elect candidates across Latin America.

McDougal and J.J. Rendón spoke for hours over two days in his Miami penthouse in May 2016, talking through whether she should sell her account of a decade-old relationship with the Republican presidential front-runner, they each confirmed after inquiries from The Washington Post. Rendón said the mutual acquaintance who arranged the meeting, Jay Grdina, had asked him to find a buyer.

“He was proposing for me to find people, people inside or outside the United States — it didn’t matter,” Rendón said. “Whoever I may know in the media or in Hollywood or in the documentary sector or politics.”

The $150,000 deal that ­McDougal eventually struck with American Media Inc. (AMI), the publisher of the National Enquirer, drew wide attention in recent weeks as she sued to be released from a non-disclosure agreement with the company and then told all — or almost all — on television. This story of an earlier attempt to sell her account has not been told.

Former Playboy model Karen McDougal, who claims to have had an affair with President Trump in 2006, reached a settlement with American Media to allow her to speak freely about the story. (Reuters)

The people involved connected in an underground marketplace where secrets about the rich and famous are a form of currency, where brokers can be compensated as readily as sellers and where buyers are not necessarily limited to media companies. The story of their effort offers a glimpse into how Trump’s political rise has turned his past into fodder for people seeking to profit in that marketplace.

 Among the central characters: McDougal, a fitness model who was the 1998 Playboy Playmate of the Year; Grdina, an entrepreneur once married to adult-film superstar Jenna Jameson; and Rendón, a student of Zen Buddhism who collects samurai swords and dresses in black to protest the repressive government of his native Venezuela. 

Though little known in the United States, where he lives in a form of exile, Rendón is a polarizing political force in Latin America, a right-leaning strategist often likened to Karl Rove. Critics cast him as a master of campaign dirty tricks. He has been accused of deploying hackers whose strategies resemble those used by Russia in the 2016 U.S. campaign.

Rendón says his tactics are legal and has sued those who suggest otherwise, including journalists, a Mexican gubernatorial candidate and the president of El Salvador. Allies describe him as a pro-democracy freedom fighter and a skilled strategist.

In interviews, including one in his Miami home, Rendón told The Post that he was never interested in buying McDougal’s story and did not shop it around. He said he advised her not to sell it.

McDougal declined requests for interviews but confirmed some details through a lawyer and provided a brief statement through a spokeswoman. McDougal acknowledged seeking advice from Rendón but said she had been unaware of the effort to enlist him to help find a buyer for her story.

Yet his name surfaced during McDougal’s negotiations with AMI, according to Dylan Howard, a senior executive at the tabloid publisher. In an interview, Howard said he was told that McDougal had an offer of $1 million from a political operative named J.J. Rendón. Howard declined to name his source and said he did not confirm that there really was an offer. 

In the statement, McDougal said: “I was never told about a $1 million offer for my story from anyone, let alone a ‘political operative.’ In my experience, J.J. would have been the last person to buy or advise me to sell my story.”

Grdina did not respond to calls and texts from The Post in the past two months, and in April, his wife, model Erin Naas, told a Post reporter to leave their property in Scottsdale, Ariz. Late Thursday, when told what this story would say, Grdina threatened a lawsuit over “falsehoods” he did not specify.

“If u choose to run my name in the story of falsehoods I will have a complaint drafted and filed faster than you could imagine against both you personally as well as the Post,” he wrote. “I would proceed wisely.”

Accusations of playing dirty

Juan José Rendón Delgado grew up in Caracas, the son of pro-democracy activists. He was a well-established political adviser by 2004, when he accused then-President Hugo Chávez of election fraud. Then — fearing retribution — Rendón left the country. 

Now, from the 46th floor of an exclusive high-rise in downtown Miami, he works to topple the Venezuelan regime. Nicolás Maduro, who this month won reelection as president of Venezuela in an election widely criticized as fraudulent, has deemed Rendón “public enemy number one.”

Rendón has notched big wins, helping to elect the current presidents of Mexico and Colombia. But he has also run into a fierce backlash from pundits and political opponents who have dubbed him the “king of black propaganda.”

Mexican presidential candidate Andrés Manuel López Obrador this year accused Rendón of being an “especialista en guerra sucia,” a specialist in dirty war, hired by a “mafia of power” to undermine him.

Rendón said López Obrador’s accusations were unfounded. The attacks on his character and tactics are, in his view, the result of persecution by the Venezuelan government and frustration among his political opponents.

“I don’t deny that I’m capable of doing very strong negative campaigns. That’s legal,” Rendón said. “If you are gay and you vote against gay rights in the Congress, and no one knows about it, and there is an election, and I can show that you contradict yourself, I will do it.”

In March 2016, Bloomberg Businessweek published an exposé accusing Rendón of hacking elections in Latin America. The story is based largely on the account of Andrés Sepúlveda, who claims to have worked for Rendón and who is now in a Bogota prison serving a 10-year sentence for interfering in Colombia’s 2014 presidential election.

Rendón denies the allegations and is suing Bloomberg for defamation in federal court in Miami. Rendón said Sepúlveda worked for him only briefly and on Web design.

In the United States, where he says he was granted asylum in 2016, Rendón has shown little consistent loyalty to any party.

During the presidential campaign that year, Rendón repeatedly needled Trump, tweeting in Spanish that Trump deserves “repudiation” and “concrete actions against his racist position.” Rendón also was critical of Democratic presidential nominee Hillary Clinton, retweeting a video montage that he wrote showed her “lying for 13 minutes straight.”

Two months after the election, Rendón backed the winner, donating $810 to Trump’s 2020 campaign and $1,013 to the Trump Make America Great Again Committee. He also gave $3,202 to the Republican National Committee.

He flew to Washington for Trump’s inauguration and attended a black-tie dinner at the Library of Congress, photos show, mingling with six-figure donors and prominent Republicans such as future secretary of state Rex Tillerson. On Capitol Hill, he draped a scarf resembling the Venezuelan flag around the neck of Sen. Marco Rubio (R-Fla.).

Rendón said he has mostly stayed away from working in U.S. politics, aside from what he described as an unproductive meeting with Libertarian presidential candidate Gary Johnson during the 2016 campaign.

Meeting in Miami

It was a tweet that set the meeting between Rendón and McDougal in motion.

On May 7, 2016, former Playboy model Carrie Stevens hinted on Twitter that McDougal had had an affair with Trump. McDougal became convinced her story would leak, according to her lawsuit against AMI. A friend, John Crawford, persuaded her to get ahead of it by telling the story on her own terms, the lawsuit says.

Within days, Jay Grdina had set up the meeting in Miami, according to Rendón.

Grdina knew McDougal because she had been married to his brother. Grdina had been introduced to Rendón a few years earlier by a Los Angeles talent agent who thought Rendón might help with international distribution of NOHO, an anti-hangover drink Grdina was marketing.  

And so on May 27, three weeks after the coy tweet about her relationship with Trump, McDougal was sitting in a penthouse apartment, looking out over the Atlantic, preparing to spill a ­decade-old secret to a man she had never met before. 

Rendón said Grdina had told him to also expect Crawford, but only McDougal showed up. 

Rendón said they spent hours that day getting to know each other. It was not until the following day — surrounded by Rendón’s collection of centuries-old Japanese swords and suits of armor — that she recounted what she said was a 10-month consensual affair. (The White House has said the president denies her allegations.)

McDougal sat on one end of a sleek white couch, Rendón on the other, he said. A maid offered coffee, and as the hours passed, they dined on sushi one day and Peruvian cuisine the other, he said.

Rendón, 54, told The Post that he viewed McDougal’s story about a love affair between consenting adults as virtually worthless. He said he warned McDougal that selling her story would bring unrelenting media attention. He also said he’s not in the business of buying, selling or brokering such secrets.

“I don’t do that,” he said.

McDougal, 47, also said Rendón never made an offer. 

“J.J. made it clear to me that he didn’t think I should pursue selling my story, and that he wasn’t interested in it,” she told The Post.

A deal takes shape

Two weeks after the meeting, McDougal hired Keith Davidson, a Los Angeles lawyer who has represented clients with embarrassing stories about celebrities. Davidson arranged for his new client to meet Howard, AMI’s chief content officer, on June 20, according to McDougal’s suit.

McDougal was joined at the law office by Grdina and Crawford, Howard said.

Davidson declined to comment, citing attorney-client privilege.

Crawford did not respond to calls and texts. Reached by phone in April, he declined to comment. 

Howard said that over the next two months, he was told by a person close to McDougal that she was talking to another potential buyer.

“It was brought to my attention at the time that Ms. McDougal was entertaining a million-dollar offer from a person described to me as a political operative who didn’t want Trump elected,” Howard told The Post. “I later was told that was J.J. Rendón.”

Howard’s recollection is corroborated in part by a document McDougal attached to her lawsuit: an undated memo by AMI officials, in response to questions from a New Yorker reporter, naming others said to be interested in buying her story. 

“She claimed she had been offered more than $1 million for the story, and was also in negotiations with ABC,” it said. “She asked AMI to counter for the rights.”

Rendón called the notion he offered a million dollars “delusional.” He said he believes his name may have been used by people close to McDougal as a bargaining chip in negotiations.

Rendón said Grdina contacted him several times over the summer of 2016, once suggesting that the story could fetch between $1.5 million and $2 million.

A deal began to take shape in which AMI — whose chief executive, David Pecker, is a friend of Trump’s — would buy but not publish the story. McDougal would sign the $150,000 deal on Aug. 6.

But before then, Grdina wanted to know whether Rendón had any leads on another buyer. Rendón showed a Post reporter several of what he said were texts from his exchanges with Grdina.

“LMK what’s up. Been dragging on,” Grdina texted July 11. “If u are not interested or ready to close, I think this story will go to a group that will bury it.”

In later texts, Rendón said, Grdina complained that his messages went unanswered. On Aug. 1, Grdina texted that he was close to a deal to bury McDougal’s story.

“That’s the best option for you and HER!!” Rendón replied.

Alice Crites, Mary Jordan, Joshua Partlow and Frances Stead Sellers contributed to this report.