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Del Valle is one of the first Puerto Ricans to have a conflict with Pierce, accusing him of deception and manipulation. During the beauty pageant, Pierce purchased 80% of the shares of the W Hotel. This transaction is one of his largest investments in Puerto Rico and paved the way for him to seek over 30 million dollars in tax breaks from the local government.
Gracia assisted in this acquisition. Court records show that he represented Pierce in meeting with local officials in Buicks, and found an architect to plan the reopening of the hotel.
However, this partnership was short-lived: In a lawsuit in 2022, Gracia claimed that after the transaction was completed, Pierce excluded him from the project and refused to pay him $790,000 in commission.
Another project on Bocas del Toro faced a similar situation. In 2021, Pierce asked a local naval engineer to help him set up a hotel and museum on a ship docked off the northern coast of the island. The engineer, who requested anonymity to avoid commercial repercussions, arranged meetings with local officials and discussed the project with the mayor, but Pierce suddenly abandoned the plan. In an interview, he claimed that Pierce still owed him $17,000 for the engineering work. (Pierce stated that he did not owe this debt.)
Last year, there were signs that Pierce was in financial trouble. He had asked De la Uz to repair the “Aurora”, his yacht used to ferry friends back and forth along the West Coast. De la Uz recalls that most of the guests were “Americans he tried to persuade for money,” portraying himself as Puerto Rico’s savior.
In a lawsuit in 2023, De la Uz claimed that he and Pierce jointly owned the yacht, and Pierce owed maintenance costs. De la Uz said that while guests were partying on the deck, the yacht was taking on water and slowly sinking into the Caribbean Sea.
Pierce declined to comment on these allegations, saying, “We are actively resolving these issues through the court to reach a fair resolution.”
“I have not done any due diligence”
When Pierce travels on the Aurora, he sometimes brings a newcomer to join the 60th district community, 62-year-old logistics tycoon Lipsey. For a while, Pierce only knew Lipsey’s nickname Jopepi. Pierce thought he was not good at socializing, but he was very likable. “I believe he is a very kind person,” Pierce said.
Pierce only knew the general situation of Lipsey’s arrival in Puerto Rico. In 2017, Lipsey made a lot of money from the relief work after Hurricane Maria through a contract with the US government. However, two years later, a legal scandal exposed his high society life in Aspen, Colorado. A wild New Year’s party hosted by the Lipsey family sparked a police investigation, and he and his wife eventually admitted to providing alcohol to minors and were sentenced to one year of probation.
The Lipsey family sold their house in Aspen and eventually moved to Puerto Rico, settling near Pierce. Soon, the two families became close. Lipsey’s wife and Pierce’s mother became fren. Pierce recalls that after Ms. Calabro passed away in 2022 due to a heart attack, Lipsey said he had promised her: he would always be there for her family.
Pierce and Lipsey have collaborated on various business projects, but the most significant transaction involved the W Hotel. Last October, Lipsey agreed to lend Pierce 10 million dollars, with 4 million dollars for purchasing the remaining 20% stake in the hotel and 6 million dollars for investing in a bankrupt chain of hospitals. These terms posed significant risks for Pierce: he had to complete the hotel transaction within two weeks. As collateral, he had to put up all his shares in the W Hotel. Pierce said he felt uncomfortable with these requirements but agreed nonetheless. “I didn’t do any due diligence,” he recalled.
One month after the protocol was signed, Lipsey accused Pierce of violating the protocol and taking control of the hotel. Lipsey later claimed in legal documents that Pierce did not use the borrowed funds as planned, but spent the money on a private plane and held a 72-hour birthday party spanning San Juan, Miami, and Los Angeles.
As the dispute escalated, Pierce arranged to meet Lipsey at the Hacienda Tamarindo hotel. The small hotel, located in Buques, was bought by Pierce for $3.2 million. Lipsey later told Puerto Rican police that the meeting was akin to a kidnapping. Pierce took his phone and locked the door, with an armed guard patrolling nearby.
In 2021, Pierce acquisitioned the boutique hotel Hacienda Tamarindo for $3.2 million
In court, Pierce denies embezzling borrowed money or kidnapping Lipsey. But one of his advisors, Cassandra Wesselman, recently moved to Puerto Rico and said that his mindset was not good when the W Hotel dispute began. Ms. Wesselman said it was her suggestion to bring armed guards to the Tamarindo estate to protect Pierce from harm by a couple living in another room. She explained that the couple belonged to a cult.
A month after the controversial meeting ended, Pierce sued Lipsey in an attempt to regain control of the W Hotel and accused him of fraud and theft.
The judge rejected Pierce’s injunction request, which should have restored his ownership of the W Hotel during the trial. Pierce and Lipsey have been in contact, discussing possible settlement options. But their friendship has come to an end.
Lipsey did not publicly discuss the dispute until July, when he spent two hours discussing it with a New York Times reporter via WhatsApp. Lipsey was smoking a cigarette and virtually touring his Tennessee home, where he spends part of the year. He opened his camera to show off his unusual art collection, including a canvas on the wall with two red paint spots. Lipsey explained that it was a piece by his son’s girlfriend.
Lipsey called Pierce “not a good person”, a terrible businessman. “He didn’t do everything he promised when he moved to Puerto Rico.”
He said the same thing in front of Pierce. Lipsey said that in a heated conversation, he called Pierce “really disappointing your mother”.
Carefree confidence
One morning in June, Pierce strolled through the old town of San Juan, winding along narrow sidewalks, pointing out his favorite spots along the way. Despite the hot weather, he was dressed in black, as he did every day, so he didn’t have to worry about time-consuming outfit choices anymore. ‘Mark Zuckerberg and Steve Jobs, these people wear the same clothes every day,’ Pierce explained.
He stopped outside the Carlyle Bar, a high-end jazz bar run by Puerto Rican pianist Muñoz. Pierce said Muñoz had created a song specifically for him and Ms. Rose. Thinking of this, he couldn’t help but laugh. ‘This song is called ‘Superhero’,’ Pierce said. (The actual name of the song is ‘Superpower’.)
Despite all the setbacks, Pierce remains confident in himself as a force for progress in Puerto Rico. However, his confidence masks the ongoing chaos in his business affairs. The conflict between Pierce and Lipsey has sparked intense speculation among his friends. Robert Anderson, a Cryptocurrency enthusiast living in Puerto Rico, is friendly with both Pierce and Lipsey, and he says their behavior is “like children”.
Pierce’s fren and colleagues said he seemed to be running out of money. Lipsey’s lawyer argued in court that Pierce lacked the ‘funds or resources’ to develop the W hotel. According to documents reviewed by The New York Times, a representative of the Puerto Rican basketball team Mets de Guaynabo sent an email to Pierce this summer, complaining that he had not paid the team’s sponsorship fee of over 25,000 dollars.
Pierce is dressed in black clothes, wearing a black hat, sitting on a chair in a white room.![]()
Pierce also expressed concerns about his personal safety in Puerto Rico. According to two people close to Pierce, he privately discussed plans to build an ammunition depot in Vieques. He said the arsenal would provide a certain level of protection if the locals turned against him.
In a 17-page statement, Pierce denies proposing the establishment of an arsenal and claims he is still wealthy, refuting claims of financial difficulties. He says the complaint from Mets de Guaynabo is a “misunderstanding” stemming from a misinterpretation of sponsorship terms, and he has now agreed to pay the fees.
However, just as The New York Times was finishing its report, a public relations person for Pierce mistakenly sent a message to a group chat including New York Times reporters and Pierce consultant Ms. Wesselman: ‘We haven’t received our pay yet.’ ‘I guess you don’t have the money to pay us, otherwise you would have done so already.’ Wesselman shrugged off the message, saying that the public relations person was ‘just teasing us.’ After learning that a reporter had seen the message, the public relations person stated, ‘Pierce always pays on time.’
Pierce defended his work in Puerto Rico. He said he had made charitable donations, including a six-figure donation, to support Covid relief efforts in the region. “Transformational projects take time,” Pierce said, “while some initiatives face challenges, others have achieved significant success.”
Among his many accomplishments, Pierce mentioned the hospital in Umacao City that he purchased at the end of 2023 - an investment he pitched to Lipsey. He said that he worked with radiologist Josué Vázquez Delgado from Puerto Rico to save the hospital from bankruptcy and retain over 90% of the employees.
However, in an interview, a doctor at the hospital, who did not want to reveal his name, said that Pierce owed him tens of thousands of dollars in wages. The doctor said that the hospital had been withholding payments to suppliers, and some surgical equipment was also insufficient. (Pierce said that his team had already solved these problems and “greatly improved the hospital’s operation”).
Last month, Pierce tried to showcase his success in Puerto Rico by taking a walk in San Juan. He led two New York Times reporters to a building he purchased in 2019, which was simply furnished with a prominent TV screen. He claimed that this building housed the world’s first Non-fungible Token art gallery. ‘You might not think of Puerto Rico as a pioneering place in the tech field,’ he said. The exhibited images include a fluorescent dinosaur living in a vast cactus forest, which Pierce said was designed by his 5-year-old daughter using artificial intelligence tools.
However, what he didn’t mention is that a luxury real estate company has already posted a notice to sell the building and held an open house. Faced with this fact, Pierce admitted that he had recently tried to sell the gallery. He explained that it has never been fully open and he has been trying to make money.