LAS VEGAS (KLAS) — Tony Hsieh’s last weeks alive appear to differ from the year prior, where the late Las Vegas entrepreneur and former Zappos CEO was caught in a downward spiral of alleged drug misuse and bad business transactions, documents the 8 News Now Investigators reviewed Wednesday said.

Hsieh died in a house fire in November 2020 in Connecticut. He was 46. That December, a judge named Tony Hsieh’s father, Richard Hsieh, and brother, Andrew “Andy” Hsieh, as co-administrators of his estate. Andy Hsieh resigned from his position this summer.

Recently filed court documents in the battle over Hsieh’s estate indicate he and a group of friends traveled to Connecticut around Nov. 1, 2020. Hsieh did not bring his security detail with him and traveled to the East Coast via plane, not by bus — bus being his preferred method of travel, documents said.

On Oct. 29, 2020, a few weeks before the fire, Hsieh “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,’” lawyers wrote in court documents. CEO Tony Hsieh poses after delivering a keynote presentation at the MAGIC clothing industry convention at the Las Vegas Convention Center February 17, 2010 in Las Vegas, Nevada. (Photo by Ethan Miller/Getty Images)

Lawyers for Hsieh’s estate have repeatedly written in court documents that he did not have the mental capacity to sign off on contracts in the months and years leading up to his death. Evidence in lawsuits filed for pieces of his wealth includes Hsieh’s reported hope of building a cashless theme park where visitors would pay in seashells.

In November 2019, Hsieh began to experiment with ketamine, which in high doses can lead to hallucinations, his family wrote in court documents. In 2020, Hsieh began using nitrous oxide as a replacement for other drugs he was taking.

Nitrous oxide, or whippets, sometimes also called laughing gas, is sold as cartridges that are inhaled. 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.

In this photo illustration, some of the thousands of empty canisters of nitrous oxide that were collected at the end of a music festival are seen on October 14, 2015 in Bristol, England. (Photo by Matt Cardy/Getty Images)

In a court filing from earlier this year, lawyers for Hsieh’s estate claim “the balance on Tony’s line of credit ballooned to more than $250 million through a series of transactions,” including a $2.2 million fixed-fee for his attorney, a $7.5 million contract for another man to provide “financial consulting services,” a third contract worth $30 million for another man to “operate a boat bar and ice castle” and the purchase of the Zappos headquarters “for nearly $40 million more than its value.”

The recently filed documents indicate Tony’s brother, Andrew, was attempting to wean his brother off nitrous oxide by controlling his brother’s access, particularly during the Connecticut trip.

“Andy Hsieh stepped into the role of supplying nitrous oxide to his brother as a means of monitoring and limiting the amount over time that his brother consumed,” court documents said.

The November trip appeared to mark a behavioral change for Tony.

“Over the next 7 days, Tony was able to significantly curb his use of nitrous oxide,” documents said. “He spent his time enjoying food and movies with his companions. His companions describe seeing Tony beginning to smile and laugh again.”

“Andy Hsieh also worked with and coordinated security to perform drug sweeps of the house and buses whenever traveling and to dispose of drugs. For example, on Tony Hsieh’s first trip to Connecticut, Andy Hsieh and the security team discovered one of the travelers was supplying Tony Hsieh with drugs so that person was escorted off the bus,” documents said.

Firefighters were called to the home at 500 Pequot Ave. around 3:30 a.m. on Nov. 18. The three-story waterfront home contains guest quarters on the basement level. That level opens to a pool area behind the house, records obtained two years ago by the 8 News Now Investigators showed. A storage area, which looks like a shed, is attached to the back of the building on that level.

Hsieh retreated to a shed on the night after a fight with his girlfriend and was using a propane heater to stay warm before the fire that killed him, investigators said. Hsieh was in a storage room with a 20-pound propane tank at the time. Lawyers for his estate said Hsieh had a “growing obsession with candles and fire” at the time.

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. Video footage obtained by investigators shows friends bringing Hsieh whip-its and a whip-it canister, the report said.

Fire officials previously told the 8 News Now Investigators that they had to force their way into the storage area and pull Hsieh out.

Surveillance video shows Hsieh opening the door to the shed as smoke appeared to be coming from it 10 minutes before his friends call 911, investigators said. An employee had been checking on Hsieh every 10 minutes, leaving Post-It Notes and knocking on the shed’s door before the fire, investigators said.

Hsieh was traveling with a nurse and a driver who stayed at a hotel nearby, investigators said in 2021. Hsieh had planned to fly to Hawaii the morning of the fire.

In the weeks before Tony’s death, Andy Hsieh became so concerned about his brother’s health, he asked that “vitamins and protein supplements” be slipped into his food, documents said. Andy Hsieh had been offered a $1 million salary to take care of his brother at the time, previous court records said.

Hsieh led retail giant Zappos for 20 years and retired as CEO back in August 2020. He played a pivotal role in the revitalization of downtown Las Vegas and had an estimated net worth in the hundreds of millions of dollars.

Lawyers for his estate and those who have filed lawsuits and creditor’s claims have repeatedly declined to comment on the ongoing legal matters.