LAS VEGAS (KLAS) — “It was madness,” singer and songwriter Jewel Kilcher said about visiting her friend Tony Hsieh in the months before the former Zappos CEO and Las Vegas entrepreneur’s unexpected death in 2020.

Kilcher’s description is included in thousands of pages of new documents, depositions and photos filed as part of an ongoing lawsuit, claiming Hsieh was unable to conduct business during his final months alive.

Hsieh, who founded and then sold the online shoe retailer, died in a house fire in November 2020 in Connecticut. He was 46. Since then, several people have filed creditors’ claims and lawsuits against the estate for payment. Previous court filings estimated his wealth at nearly $850 million.

Lawyers representing Hsieh’s estate filed the documents in a lawsuit from Hsieh’s former lawyer, Puoy Premsrirut. Last month, a Clark County judge ruled in Premsrirut’s favor in her lawsuit over a $2.2 million fixed fee — a contract she signed with Hsieh in August 2020, documents said.

Lawyers for Hsieh’s estate have repeatedly written in court documents that Hsieh did not have the mental capacity to sign off on contracts in the months and years leading up to his death.

Tyler Williams shared this photo of him and Tony Hsieh. (Tyler Williams)

Tyler Williams met Hsieh in 2011.

“I think one of the hardest things for me, outside of losing Tony, was the recognition that money’s a powerful motivator,” Williams said.

William began his career at Zappos in 2011. He would eventually rise to the ranks of director of brand experience.

His real role — friend and right-hand man.

“It was inspirational,” Williams said, “It was, ‘Let’s solve real-world problems. Let’s help make a better place for people to work and live.’”

Tony Hsieh poses after delivering a keynote presentation at the MAGIC clothing industry convention at the Las Vegas Convention Center on February 17, 2010 in Las Vegas, Nevada. (Photo by Ethan Miller/Getty Images)

Williams would work with Hsieh to develop both Zappos and downtown Las Vegas. By late 2019, the methodical multi-millionaire was marching toward disaster.

“In the conversations that I was having with him, it was like, I couldn’t pull him back into reality and it was super scary,” Williams said.

That reality was clouded by ketamine, an anesthetic that when misused can cause hallucinations. Friends said Hsieh began snorting the powder.

As the 8 News Now Investigators have reported, while Hsieh lived in Las Vegas, he purchased more than a dozen multi-million-dollar properties and lived most of the last year of his life in Park City, Utah.

Those in and around Hsieh’s inner circle came to Williams in late 2019 and early 2020 with their concerns.

“And I think generally, most people were concerned about his reputation around that time,” Williams said.

Hsieh was admitted to a rehabilitation program for two weeks in February 2020, documents said. On a medical form, an employee wrote that Hsieh was “manic” and had “grandiose” delusions. “Residential initially presented in a thoughtful and well-stated manner,” the employee wrote about Hsieh. “His premise began to deteriorate as he discussed his ‘research’ into ketamine and how it has expanded his cognitive, physical, and spiritual capabilities, including his ability to grow an additional ‘two inches.’”

Hsieh asked Williams to create a list of his concerning behaviors following his two-week stay.

“When he was saying these things to you, what was going through your mind?” 8 News Now Investigator David Charns asked Williams.

Tony Hsieh was admitted to a rehabilitation program for two weeks in February 2020, documents said. On a medical form, an employee wrote that Hsieh was “manic” and had “grandiose” delusions. (KLAS)

“It’s the compounding effect of one of those things might be, ‘OK, you think you can run a marathon without training,’ but it’s all of those things combined of, ‘I’m transcending human consciousness,’ ‘I can see the Matrix,’ ‘I can grow myself with just my brain,’ ‘I can heal people,’ these types of things he was saying all combined just definitely set off every alarm inside of me that my friend’s not OK,” Williams said.

Hsieh remained isolated in Park City during the first few months of the COVID-19 pandemic. According to friends, he believed he could recycle urine and manifest water.

“Is it fair to say the Tony Hsieh you were working with at Zappos and the Tony Hsieh you saw in Park City were different people?” Charns asked Williams.

“Completely opposite of each other,” Williams said.

Tony Hsieh asked his friend, Tyler Williams, to create this list of his concerning behaviors following Hsieh’s two-week stay in rehab. The line after item 13 indicates the separation of pre- and post-rehab behaviors, according to Williams. (KLAS)

Williams’ turning point came on a bus trip to Montana that June.

“He walks on the bus in his underwear with like a box of crayons and Post-It notes,” Williams said.

“At what point did you realize, ‘The emperor had no clothes?’” Charns asked.

“That bus trip where he had a complete psychotic break right in front of his friends we all knew in that moment he’s not just not OK, he’s completely out of his mind,” Williams said.

Friends found Hsieh in the bus’s bathroom spreading feces on himself in an attempt to “reabsorb minerals,” documents said. Hsieh turned around once the group reached Park City. Once at home, he flooded the mansion and held two women hostage, prompting officers to take him to the emergency room. There, a doctor diagnosed him with an “altered mental status,” documents said.

In June 2020, Tony Hsieh flooded his mansion and held two women hostage, prompting officers to take him to the emergency room. There, a doctor diagnosed him with an “altered mental status,” documents said. (KLAS)

“This patient was brought in by EMS when some friends found him altered,” the doctor wrote in his or her notes. “They think he may have been doing some illicit substances, including perhaps mushrooms.”

Officers “felt that they needed to bring him directly to the emergency department to get the additional help because they did not feel like he was safe at home taking care of himself and his altered state,” documents said.

“Some people were calling it, ‘He’s in a funk.’ ‘He’s just depressed.’ Or, ‘He needs something that will pull him out of this depression or this self-destructive behavior,’” Williams said. “And you had a new group of people who were forming that were really interested in the financial gains.”

Williams later sent a text message to the person he believed was supplying Hsieh with ketamine in an attempt to stop the flow.

“I said, ‘Hey please don’t — whatever you do, Tony just had a psychotic break, please don’t give him Ketamine,’” Williams said. “’Whatever you do, don’t give him Ketamine.’ And that person showed Tony that text message.”

Hsieh then responded to Williams, cutting him off. When Williams dictated that text message, the reading lasted several minutes.

“That was the very last time I ever had any communication with him,” Williams said. Soon after, Hsieh’s incoherent stream of consciousness was silenced.

“Hundreds of people that used to talk to me, regularly, on a regular basis, when Tony told them that I was no longer to be communicated with, just immediately stopped talking to me,” Williams said. “Immediately.”

Tony Hsieh’s friend, Jewel Kilcher, took this photo outside Tony Hsieh’s Utah home, according to court documents. It shows empty nitrous oxide canisters all over the ground. (KLAS)

Court documents filed by Hsieh’s family in 2021 indicated Hsieh used ketamine and nitrous oxide in the years before his death. According to friends, Hsieh used “as many as 50 cartridges of nitrous oxide a day, often in public, or during ‘meetings’ with people,” documents said. Court documents also said Hsieh’s bedroom was “littered with hundreds of spent nitrous oxide cartridges.”

Lawyers for Hsieh’s estate have claimed millions of dollars of real estate were inflated in cost and at times were based on Tarot cards, they write.

Kilcher and her business partner, Ryan Wolfington, visited Hsieh in Park City in August 2020. In addition to comments about the last time she saw her friend alive, Kilcher describes Hsieh as a quiet, smart man.

“Very laid back. Very consensus building. Very bright. Not overly talkative,” Kilcher said in one deposition described Hsieh before 2020 from September 2021 and released in court documents. “He was probably a little more of an introvert, even though he surrounded himself with so many people.”

Kilcher and Wolfington visited Hsieh as he sat outside on a beach, documents said. Hsieh was working on a “Park City Project,” which would be built as a ranch where visitors would be “centered around the idea of no shoes, no tech, and no obligations,” court documents said. He referred to the park as “Disneyland 2.0” and “County Zero.”

Jewel Kilcher took this photo of Tony Hsieh uses nitrous oxide in his Park City, Utah, home in August 2020, according to court documents. (KLAS)

This is how Hsieh described it at a meeting in September 2020: “Ten X-Men because it’s going to be ten times better than — meets Ted talks, meets Ted, meets Burning Man. We’re actually going to have a Burning Man party on Saturday — that we’re planning. Meets MacGyver, meets circus, meets kids’ entrepreneurial education center…”

The ranch, or “cashless theme park” was to require tarot cards for entry. Hsieh believed he could convince four billion people to live around his County Zero ideals, adding he wished to purchase hot air balloons to broadcast to people across the world and tour buses to bring people to his theme park.

“Tony used to always say, ‘If you had a magic wand and anything was possible and regulations and resources weren’t a problem, what would you do?’” Williams said. “So yes, we thought about big ideas. Then those ideas would go into a processing system around him that people who were rational and could tell him that, we looked into this this doesn’t make sense here’s why, none of those people were left.”

As the 8 News Now Investigators previously reported, throughout 2020, lawyers for Hsieh’s estate said, “continued [abuse of] hallucinogenic and dissociative substances, including nitrous oxide, which combined with his delusional thinking, fundamentally destroyed Tony’s ability to exercise reasonable diligence and judgment, and rendered him vulnerable to those seeking to take advantage of him,” they wrote in court documents.

Park City police filed this report after responding to Tony Hsieh’s home for a welfare check in August 2020. (KLAS)

In late August, Park City police responded to Hsieh’s home for a welfare check. Police met him and private security on a front porch.

“He appeared to be in good health from what I can tell,” an officer wrote in documents the 8 News Now Investigators obtained.

“Tony was naked in his underwear,” Kilcher said about seeing Hsieh. “Only wearing his underwear. He was emaciated. He must have lost 40 pounds. He was emaciated. He was not meditating. He was doing Whip-It after Whip-It after Whip-It to the point where there were – they were littered all over where he was.”

The documents include two photos Kilcher took of Hsieh in his bedroom. In the photo, Hsieh is nearly naked and holding a Whip-It canister. Other court documents said Hsieh constantly ran the shower and other bathroom fixtures, flooding the room. Kilcher and Wolfington said the home was covered in feces and dirty, documents said.

“It doesn’t even look like him,” Williams said about the photos.

Court documents filed by Tony Hsieh’s estate include this photo of him with a candle in his lap and writing all over his body. (KLAS)

“I believed he was having a psychotic break,” Kilcher said. “Everything he was saying was unfounded in reality, and he had never spoken like this before. He had a canister that looked like a – an industrial-strength whipped cream shipper that you would screw these nitrous oxide cartridges into, except, obviously, there was no whipped cream in there. And he would just push the level and inhale the nitrous oxide.”

“I remember seeing candles everywhere, wax everywhere,” Wolfington said. “So, candles are everywhere, and then they’re melted down to nothing. And Tony did say, I don’t want those removed, I want nature to decompose them. That was part of his thing.”

“Multiple individuals seized on Tony’s vulnerability to enrich themselves at Tony’s expense,” lawyers for the Hsieh estate write in the documents filed in March. “Dozens of separate and distinct transactions and financial commitments were procured from Tony in his diminished state, resulting in hundreds of millions of dollars of Tony’s money being spent by the time of his death.”

Between March 2020 and October 2020, Hsieh acquired nearly $90 million in Utah real estate assets, documents said.

Transactions went forward on pieces of paper with the wording: “Does Tony approve?” Estate lawyers said the transactions include the purchase of the Zappos Headquarters in downtown Las Vegas for $30 million over its actual value and a $3.5 million payment for a “sham production project” called Freeform, documents said. In her ruling last month, the judge ruled in Premsrirut’s favor, however, other claims from the estate regarding the sale are pending.

Between March 2020 and October 2020, Hsieh acquired nearly $90 million in Utah real estate assets, documents say. (KLAS)

“It got this far because instead of his community rallying to try to work together in love to save a friend, the community fractured into different groups of people that had different interests in mind and the group of people that were around him when he was like this didn’t have his best interests at heart,” Williams said.

“I brought up that he wasn’t well and that I was worried people were taking advantage of him and that this whole situation seemed really unhealthy and – and crazy,” Kilcher said about visiting Hsieh. “I was worried that he was secluded and isolated from getting help. I said I was worried he was going to die from malnutrition or drug use.”

Kilcher and Wolfington described how they brought their concerns to others in Hsieh’s inner circle and how Hsieh would sign off on business deals with Post-It notes and notes slipped under his door, documents said.

“This was haphazard,” Kilcher said in her deposition. “It was half-baked. It was ill-conceived ideas on random pieces of paper. It – it was – it was madness.”

“He’s like a mad genius, you know, like he gets — he likes to go into these states because that’s where he gets his creative ideas,” Wolfington said about what one person in the inner circle told him. “And he’s really like in one of the most amazing, giving, creative spaces in his career. I told Jewel, that is the darkest side of humanity that I’ve ever seen. To know I was being bribed literally straight up in such a subtle, but overt way, and the narrative which they had been telling the whole time, which is Tony is just a creative genius and he just wants to help a kid.”

Tony Hsieh accumulated items outside his home in Park City, Utah. Hsieh believed he created a “natural dishwater” and offered a person $1 million to serve as a tour guide on this pond, according to court documents. (KLAS)

By the end of October, Hsieh feared for his safety and believed he was in an artificial intelligence simulation, documents said.

“[He] believed that he could live without oxygen,” Hsieh’s friend said in his deposition. “He believed that he could grow his body to be seven feet tall, in order to run the fastest marathon without training. He believed that he could morph his body into a gazelle. He believed that he could download skills from – like – like you would in ‘The Matrix.’”

“He’s not in a good space at all,” a friend said in a text message sent on Oct. 23, 2020. “He needs help. We don’t have a lot of time to solve this equation. It’s not sustainable.”

“There wasn’t an active plan to take Tony against his will, but there were discussions regarding the possibility,” a doctor said in his tape deposition. “I was asked if – if that were a plan, if I would be willing to participate in it.”

“Given recent events, I would like to halt any new business due to the question of decision making,” Premsrirut emailed on Oct. 25. “Until I am confident about [Tony Hsieh’s] condition and capacity, I do not feel comfortable accepting ‘his word’ or ‘his instruction’ from others.”

A photo of Tony Hsieh from September 2020, weeks before he would die from injuries he sustained in a fire in Connecticut. (KLAS)

That day, a person texted that Hsieh had walked barefoot all over a floor covered in glass, documents said.

Premsrirut later “consulted with a medical doctor to discuss having Tony involuntarily committed,” lawyers said.

“Just weeks before his death Tony was taken to the emergency room after stating that he believed that he was ‘crystalizing,’ that he believed he was in a simulation, that he had been chewing cigarettes, and professing, ‘I just don’t know what’s real and what’s not,’” court documents said.

Before the 2020 fire, Hsieh had retreated to a shed at a Connecticut home after a fight with his girlfriend and was using a propane heater to stay warm before the fire that killed him, the 8 News Now Investigators reported.

Tony Hsieh Photos from scene
The pool shed where Tony Hsieh slept before the November 2020 fire. (KLAS)

According to witness reports, Hsieh was lying in a storage area with a blanket near candles. Part of the blanket and a plastic bag had caught fire earlier in the night, the report said.

“As much as Tony invested into his community and into systems that fostered connection, when he needed his community the most, when he needed society the most, it just wasn’t there,” Williams said.

No person has ever been charged with a crime in connection with the claims or evidence. Attorneys for Premsrirut did not respond to a request for comment. Several lawsuits were underway in the estate’s attempt to unwind Hsieh’s business dealings.