Evolving strategy and inside connections contributed to the freedom of Josh Holt

Jul 23, 2020, 9:43 AM | Updated: Dec 30, 2022, 11:25 am

el helicoide caracas...

From Venezuela to Florida and Texas and then again to Massachusetts, immigrants were promised work in the states. Photo: Getty Images

Editorial note: This is the latest in a series of articles related to the KSL Podcast, “Hope In Darkness.” Find all of our episodes and coverage here

SALT LAKE CITY — The team that eventually succeeded in securing the freedom of Utahn Josh Holt and his Ecuador-born Venezuelan wife wound up shifting its strategy repeatedly over time to figure out what would work best. 

Inside connections to top Venezuelan officials ultimately played a role in the case, as revealed in the latest episode of the podcast, “Hope In Darkness: The Josh Holt Story.” 

“I don’t know when you’ll be freed” 

The first shift in the legal strategy for Josh and Thamy Holt came because of an important conversation with the warden at El Helicoide prison. The couple sought a meeting with the warden after Holt became aware that one of his cellmates intended to kill another inmate in the prison. 

“I, at first, didn’t think anything of it,” Holt said in the podcast. “But as I started talking to my parents, telling my parents what was going on, they started to get really worried. And they told me, they said, ‘Josh, you’ve got to get out of there.'” 

His parents, Laurie and Jason Holt, worried if his cellmate carried out his plans, Josh would be considered guilty by association and it would derail any attempts to free him. Through a friend of Thamy’s, they arranged a meeting with the warden. The warden arranged to have Josh Holt moved to a new cell, waiting a period of days so none of his cellmates would connect the raid on their cell that would expose the plot to Josh directly. But the warden also gave the Holts some troubling insight. 

“He says, ‘You know, you guys were actually going to be released two days ago. But the reason you weren’t released was because of your lawyer and the things that your lawyer was saying about you. And since this lawyer was saying these things about you, people in this government don’t want you freed anymore. I don’t know when you’ll be freed,'” Josh Holt remembered. 

The Holts were stunned. Basically, the warden said the attorney’s strategy, labeling them as political prisoners and comparing them in the news media to well-known opposition activists in Venezuela, had backfired. 

More shifts in strategy for Josh Holt

josh holt legal strategy

Utah immigration attorney Carlos Trujillo, top right, played an important part in shaping strategy for the Holt family. Here, the family celebrated after securing paperwork to allow their daughters to stay in the United States. Clockwise from left: Thamy Holt, Josh Holt, Carlos Trujillo, Marian and Nathalia. Photo courtesy of the Holt family

Carlos Trujillo, the Utah immigration attorney who started working with Holt’s parents just before Josh and Thamy marked one year in prison, immediately got to work. He wanted to shift the strategy to portray Josh and Thamy Holt as two innocent people with no political designs. 

“[We tried] to take the politics out of everything,” Trujillo said. 

Next, he set about replacing the legal team on the ground in Venezuela — in part to help paint that picture, but also to have someone less adversarial to the government involved on their behalf. It would also help to have someone in place who knew the system. 

“To work together with the judicial part of things,” Trujillo said. “So it was having somebody on the inside for government purposes, but it’s also having somebody on the inside who can deal with the judicial system.”

Finally, the legal team looked for connections to the Venezuelan government in another way. The strategy was to find someone on the inside, someone who could reach the highest levels of government officials directly and intercede for Josh Holt. But they didn’t know where to start. 

As it turned out, the inside connections found them. 

The Old Boy Network 

In the United States, the “Old Boy Network” refers to the way powerful businessmen tend to help other powerful businessmen stay in power, through school, work or even political connections.

Perhaps Venezuela business deals weren’t cemented on the golf course, but they needed to figure out where those deals were happening and get an insider involved. They needed to figure out how to tap into Venezuela’s Old Boy Network. 

Far from Utah or Venezuela, Bill Duker picked up a newspaper.

“I had read an article in the New York Times about Josh’s situation and took advantage of the fact that we were meeting in New York with a variety of people connected with Venezuela who I thought might be able to help,” Duker said. 

Duker, a successful venture capitalist who once owned the world’s sixth largest yacht, knows a thing or two about life in prison. He served several years behind bars after he overbilled the government in legal action involving failed savings and loan companies, a situation that also got him disbarred. 

Connecting the dots to Josh Holt

After Duker’s release, he bounced back, making millions by investing in promising up and coming companies. One of those led him to Josh Holt. 

“I have a company that has a software product that could be used for internal investigations, among other things. It’s a document-management company that very quickly indexes and categorizes what’s referred to as unstructured data — emails, Word documents, that sort of stuff,” he said. 

A private investigator approached Duker to see if the software could help in a potential legal case. The P.I. suspected oil trading companies were devaluing petroleum from Venezuela’s state-run oil company, PDVSA, on purpose, by underbidding. 

“The damages are in the multibillion dollar range, perhaps $25 billion or more,” Duker said. 

In the course of assisting that private investigator, Duker suggested he connect with David Boies, a well-known New York litigator

Boies is the lawyer behind a myriad of high-profile cases, including Bush v. Gore (he represented Al Gore). He helped the

david boies josh holt strategy

In this file photo, David Boies, lawyer for one of the alleged victims, speaks outside the courthouse after billionaire financier Jeffery Epstein appeared for a hearing on July 8, 2019 in New York City. (Photo by Stephanie Keith/Getty Images)

government successfully prosecute Microsoft. More recently, he gained a measure of public notoriety for his connection to disgraced former billionaire Elizabeth Holmes and her company, Theranos. He’s also represented Hollywood movie producer Harvey Weinstein. 

“David has a huge reputation, and a huge capacity, not only for law, but for generosity,” said Duker, “and a spirit that is dedicated to people who need his help.” 

Boies, who was already representing the nephews of Venezuela’s first lady, Cilia Flores, in a drug case in the United States, agreed to represent PDVSA.

Duker went on to help fund the lawsuit and got to know a lot of the players involved. When he read the story about Josh Holt in the newspaper, he decided to ask around and see if someone could help. 

“There was some indication that that might be possible, so we began to talk to other people in Venezuela who had influence down there,” he said. 

That led Duker to Venezuelan shipping tycoon Wilmer Ruperti. 

A shipping tycoon with connections

Ruperti’s name sounded immediate warning bells for Trujillo, the Venezuelan-born Utah immigration attorney. 

“Who was Mr. Ruperti? Okay. The family was approached by the attorneys in New York, but when they mentioned Mr. Ruperti’s name, you know, as a Venezuelan, your alarms go off,” said Trujillo. “Not in a bad way, but you know, you recognize that name.” 

hugo chavez

Venezuelan President Hugo Chavez speaks during a news conference at Miraflores Presidential Palace April 15, 2002 in Caracas, Venezuela. Chavez was ousted and arrested April 12, 2002 by his military high command but returned after a collapsed coup along with a loyalist troops rebellion and protests. (Photo by Oscar Sabetta/Getty Images)

Ruperti, a former oil tanker captain, enjoyed a lot of favor with Venezuelan President Nicolás Maduro. His ties to the regime go back to 2002, when business leaders shut down the oil industry in an attempt to oust Maduro’s predecessor, Hugo Chavez. Ruperti helped keep PDVSA and the Chavez government afloat during the industry shutdown. The attempted coup failed, and Ruperti maintained close ties to government leaders as he became one of the wealthiest men in Venezuela. 

In 2018, Ruperti was also helping fund the legal defense of the nephews of Venezuela’s first lady, Cilia Flores. Through this shared connection to David Boies, Ruperti agreed to help the Holts. But the offer was met with some heartburn on Thamy Holt’s part. 

“Thamy, being Venezuelan, and knowing who Mr. Ruperti represents or who he was — it was quite a conflict on her conscience,” Trujillo said. “[For her] to say, ‘Okay, I don’t feel comfortable with this person being involved.'” 

“Even I do not understand how or why he decided to help us,” Thamy Holt said in Spanish for the Hope In Darkness podcast. “It is still, in my mind, the unknown.”

“You kind of have him up there in a tier where you put Maduro, Hugo Chavez, because they were the people that [were] showing how the corrupt government was benefiting them,” Trujillo said. 

“Judging people by their cover” 

Ruperti was well-connected, not just to political officials, but also to the SEBIN — the Bolivarian National Intelligence Service, which is Venezuela’s secret police. 

“His son’s godfather was the director of SEBIN — he was the director over where I was being held,” Josh Holt said. 

Ruperti’s involvement not only changed the strategy, it directly resulted in improved living conditions for Thamy and Josh Holt in prison. He visited them in person, occasionally bringing gifts. His connections resulted in protection for the Holts inside El Helicoide. 

“He paid so that nothing would happen to us,” Thamy Holt said. 

The experience opened Trujillo’s and Thamy Holt’s eyes. 

“I kind of received a life lesson, that — you know, we shouldn’t be judging people by their cover,” Trujillo said. “Even if he didn’t end up being the key person to make them be free, there were times that were so dire for Josh and Thamy that without him, their lives would have definitely been in greater danger.” 

Hope In Darkness releases new episodes weekly on Wednesdays. Subscribe free on Apple Podcasts, Google Play or wherever you listen to podcasts.

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Evolving strategy and inside connections contributed to the freedom of Josh Holt