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Zappos CEO Tony Hsieh went on $50M buying spree in Park City in the months before his death

Zappos’ former CEO Tony Hsieh went on a massive buying spree snapping up at least seven multi-million dollar homes, a private club and a vacant lot in the months leading up to his shocking death, DailyMail.com has discovered

Zappos’ former CEO Tony Hsieh went on a massive buying spree, snapping up at least seven multi-million dollar homes, a private club and a vacant lot in the months leading up to his shocking death, DailyMail.com has discovered.

He spent at least $50 million as part of his plan to relocate to the millionaires’ playground of Park City, Utah.

Impishly, the alcoholic and increasingly drug-addled businessman called the company he used to finance his real estate splurge ‘Pickled Investments.’

But he failed to get the last laugh. His plans ended with his November 27 death following a suspicious fire nine days earlier in his girlfriend Rachael Brown’s home in New London, Connecticut.

Candle-loving Hsieh was locked in a shed at 3.30am when it caught fire. Authorities have ruled the blaze an accident, saying he died from smoke inhalation.

Hsieh, 46, stepped down from Zappos in August after continuing to lead it for a decade after he sold the online shoe-seller to Amazon for $214 million. His estimated wealth at the time of his death was $840 million.

‘He hadn’t finished buying when he died. There were other deals in the works which sadly will never now come off,’ one real estate source told DailyMail.com. 

The jewel of Hsieh’s Park City buying binge is Crescent Ranch, a 17,350 sq. ft. mansion on a private lake. It is believed he paid just under $15 million – far more than the $12.5 million asking price. 

The Wall Street Journal said he fell in love with the 11-bedroom property so much that he asked the owners not to return as he wanted to move in immediately.

The jewel of Hsieh's Park City buying binge is Crescent Ranch, a 17,350 sq. ft. mansion on a private lake. He is understood to have paid roughly $15 million - far more than the $12.5 million asking price

The jewel of Hsieh’s Park City buying binge is Crescent Ranch, a 17,350 sq. ft. mansion on a private lake. He is understood to have paid roughly $15 million – far more than the $12.5 million asking price 

'He hadn't finished buying when he died. There were other deals in the works which sadly will never now come off,' one real estate source told DailyMail.com

‘He hadn’t finished buying when he died. There were other deals in the works which sadly will never now come off,’ one real estate source told DailyMail.com

The Wall Street Journal said he fell in love with the 11-bedroom property so much that he asked the owners not to return as he wanted to move in immediately

The Wall Street Journal said he fell in love with the 11-bedroom property so much that he asked the owners not to return as he wanted to move in immediately

Impishly, the alcoholic and increasingly drug-addled businessman called the company he used to finance his real estate splurge 'Pickled Investments'

Impishly, the alcoholic and increasingly drug-addled businessman called the company he used to finance his real estate splurge ‘Pickled Investments’

Paul Benson, a real estate agent who represented the sellers said he later went to the huge house to retrieve the owners' belongings and discovered 1,000 candles burning inside

Paul Benson, a real estate agent who represented the sellers said he later went to the huge house to retrieve the owners’ belongings and discovered 1,000 candles burning inside

His generosity was well known in his adopted town. 'He saved Park City's butt during the pandemic,' one source said

His generosity was well known in his adopted town. ‘He saved Park City’s butt during the pandemic,’ one source said

Hsieh's generosity was legendary. Scott Roeben, who runs the Vital Vegas website told DailyMail.com that the shoe magnate reputedly visited several Park City restaurants and gave them each $10,000 as a down-payment on meals that his people would eat in the future

Hsieh’s generosity was legendary. Scott Roeben, who runs the Vital Vegas website told DailyMail.com that the shoe magnate reputedly visited several Park City restaurants and gave them each $10,000 as a down-payment on meals that his people would eat in the future

The mansion, complete with a private beach, well-stocked wine cellar, sauna, indoor pool and 13 bathrooms, was a far cry from the tiny Airstream trailer that the eccentric Hsieh called home in Las Vegas

The mansion, complete with a private beach, well-stocked wine cellar, sauna, indoor pool and 13 bathrooms, was a far cry from the tiny Airstream trailer that the eccentric Hsieh called home in Las Vegas

He installed a giant metal sculpture of an octopus alongside the drive

He installed a giant metal sculpture of an octopus alongside the drive

Hsieh also bought a lot abutting his new mansion (pictured) for extra privacy and seven other properties close to the ski slopes, spending at least another $35 million

Hsieh also bought a lot abutting his new mansion (pictured) for extra privacy and seven other properties close to the ski slopes, spending at least another $35 million 

PROPERTIES HSIEH  BOUGHT BEFORE HIS DEATH 

March 27 – $3,995,000: 1422 Empire Avenue, 4,395 sq. ft. 5-bed, 6-bath

July 22 – $4,000,000: 430 Empire Avenue, 3,300 sq. ft. 5-bed, 5.5-bath 

July 27 – $3,995,000: 911 Empire Avenue, 3,251 sq. ft. 4-bed, 5-bath 

July 29 – $ 15,000,000: 2636 Aspen Springs Drive, 17,350 sq. ft. 9-bed, 13-bath

July 29 – $1,300,000: 2630 Aspen Springs Drive, vacant lot 

August 8 – $2,995,000: 1414 Empire Avenue, 3,471 sq. ft. 5-bed, 5.5-bath

August 8 – $4,000,000: 657 Park Avenue, 3,750 sq. ft. 3-bed 3 full, 2 half bath

August 8 – $3,195,000: 973 Woodside Avenue, 3,000 sq. ft. 4-bed, 4-bath

August 8 – $5,575,000: 1207 Lowell Avenue, 2,924 sq. ft. 4-bed, 5-bath  

He installed a giant metal sculpture of an octopus alongside the drive.

Paul Benson, a real estate agent who represented the sellers said he later went to the huge house to retrieve the owners’ belongings and discovered 1,000 candles burning inside.

The mansion, complete with a private beach, well-stocked wine cellar, sauna, indoor pool and 13 bathrooms, was a far cry from the tiny Airstream trailer that the eccentric Hsieh called home in Las Vegas.

Hsieh also bought a lot abutting his new mansion for extra privacy and seven other properties close to the ski slopes, spending at least another $35 million.

The cheapest of the homes was listed at $2,995,000. Others were offered at up to $6 million, but he was so determined he would pay over the asking prices.

DailyMail.com visited all seven properties, which are within a stone’s throw of each other close to Park City’s center and ski resort but did not get a reply at any of the homes. 

Many had no furniture inside. One of them is the now-shuttered Big Moose Yacht Club, a private club and bar.

Hsieh’s generosity was legendary. Scott Roeben, who runs the Vital Vegas  website told DailyMail.com that the shoe magnate reputedly visited several Park City restaurants and gave them each $10,000 as a down-payment on meals that his people would eat in the future.

‘He was very magnanimous,’ Roeben said. ‘But these people were taking advantage of him — they were sycophants and yes men who never told him ‘no.’

His generosity was well known in his adopted town. ‘He saved Park City’s butt during the pandemic,’ one source said. 

‘He would spread the wealth, using different real estate agents for each property and buying expensive meals for his hangers-on at restaurants that have been struggling.’

One of the places he frequented was Café Terigo, renting out the patio area every Thursday night from June through October. 

One waiter there told DailyMail.com: ‘He had several people come in with him who would eat and drink for free. They all seemed professional, business types with their families. But Tony himself…he was weird.’

Stories abound about his strange behavior. Just after buying his mansion he had his employees line up like football players creating a tunnel at the start of a game and he ran through them shirtless waving and high-fiving them.

One story doing the rounds in Park City was how Hsieh’s private chef, Adam Walker — who would not comment — would serve him food as he lay naked in bed.

‘There was nothing sexual about it, just the general strangeness that surrounded everything he did.

‘He wanted his food deconstructed. For example, if he had a pasta dish, he would have the sauce and the noodles separated.’

He spent at least $50 million as part of his plan to relocate to the millionaires' playground of Park City, Utah, including this home estimated at $3M

He spent at least $50 million as part of his plan to relocate to the millionaires’ playground of Park City, Utah, including this home estimated at $3M

DailyMail.com visited all seven properties, which are within a stone's throw of each other close to Park City's center and ski resort but did not get a reply at any of the homes

DailyMail.com visited all seven properties, which are within a stone’s throw of each other close to Park City’s center and ski resort but did not get a reply at any of the homes

His generosity was well known in his adopted town. 'He saved Park City's butt during the pandemic,' one source said

His generosity was well known in his adopted town. ‘He saved Park City’s butt during the pandemic,’ one source said

DailyMail.com visited all seven properties, which are within a stone's throw of each other close to Park City's center and ski resort but did not get a reply at any of the homes. Pictured: This home is worth $5,575,000

DailyMail.com visited all seven properties, which are within a stone’s throw of each other close to Park City’s center and ski resort but did not get a reply at any of the homes. Pictured: This home is worth $5,575,000

Hsieh also bought a lot abutting his new mansion for extra privacy and seven other properties close to the ski slopes, spending at least another $35 million. Pictured: This home is worth just under $4M

The Wall Street Journal said he went on a 26-day alphabetized diet, only eating food beginning with the letter A on the first day, B on the second, and so on. 'The final Z day amounted nearly to fasting,' friend Paul Carr told the publication

The Wall Street Journal said he went on a 26-day alphabetized diet, only eating food beginning with the letter A on the first day, B on the second, and so on. ‘The final Z day amounted nearly to fasting,’ friend Paul Carr told the publication

Before moving to Park City, Hsieh was a regular visitor to the town's Sundance Film Festival, which he regularly attended with actor David Arquette

Before moving to Park City, Hsieh was a regular visitor to the town’s Sundance Film Festival, which he regularly attended with actor David Arquette

DailyMail.com visited all seven properties, which are within a stone's throw of each other close to Park City's center and ski resort but did not get a reply at any of the homes. Pictured: A five-bed, five and a half bathroom home worth $4 million that Hsieh snapped up

DailyMail.com visited all seven properties, which are within a stone’s throw of each other close to Park City’s center and ski resort but did not get a reply at any of the homes. Pictured: A five-bed, five and a half bathroom home worth $4 million that Hsieh snapped up

One of them is the now-shuttered Big Moose Yacht Club, a private club and bar, worth $4M

One of them is the now-shuttered Big Moose Yacht Club, a private club and bar, worth $4M

Many of the homes had no furniture inside. Pictured: One of Hsieh's properties, listed at just under $4M

Many of the homes had no furniture inside. Pictured: One of Hsieh’s properties, listed at just under $4M 

The Wall Street Journal said he went on a 26-day alphabetized diet, only eating food beginning with the letter A on the first day, B on the second, and so on. ‘The final Z day amounted nearly to fasting,’ friend Paul Carr told the publication.

He was also pushing himself harder and harder, sleeping just four hours a night and climbing the three highest peaks in Southern California in a single day.

Before moving to Park City, Hsieh was a regular visitor to the town’s Sundance Film Festival, which he regularly attended with actor David Arquette. 

Every year he would rent out the Blind Dog Sushi restaurant on the Saturday night and insist all guests be handed a glass of the Italian aperitif fernet at the door.

‘Along with Grey Goose vodka, it was his favorite drink, but hardly anyone else would touch it. But he would personally drink bottles of the stuff,’ said one regular at the parties.

Hsieh’s drug use had increased massively since he left Zappos, numerous publications have reported. 

He inhaled nitrous oxide — laughing gas — using ‘whippets’ straight from the cartridge of a whipped cream dispenser. 

He also had become increasingly dependent on the date-rape drug ketamine, although it is not suggested that he used it on others.

The Wall Street Journal said he had begun experimenting with mushrooms and ecstasy.

Hsieh's drug use had increased massively since he left Zappos, numerous publications have reported. He inhaled nitrous oxide ¿ laughing gas ¿ using 'whippets' straight from the cartridge of a whipped cream dispenser

Hsieh’s drug use had increased massively since he left Zappos, numerous publications have reported. He inhaled nitrous oxide — laughing gas — using ‘whippets’ straight from the cartridge of a whipped cream dispenser 

Candle-loving Hsieh was locked in a shed at 3.30am when it caught fire. Authorities have ruled the blaze an accident, saying he died from smoke inhalation

Candle-loving Hsieh was locked in a shed at 3.30am when it caught fire. Authorities have ruled the blaze an accident, saying he died from smoke inhalation 

Pictured: TV personality Mario Lopez (second from left) with Zappos.com CEO Tony Hsieh (center) with Rachael Brown (second from right)

Pictured: TV personality Mario Lopez (second from left) with Zappos.com CEO Tony Hsieh (center) with Rachael Brown (second from right)

And though it only took firefighters minutes to force their way in and drag him out, it was too late to save him. 'One victim being pulled from the fire now ¿ unresponsive,' a firefighter says just eight and a half minutes into the call. The fire was reported as under control moments later

And though it only took firefighters minutes to force their way in and drag him out, it was too late to save him. ‘One victim being pulled from the fire now — unresponsive,’ a firefighter says just eight and a half minutes into the call. The fire was reported as under control moments later

The fire broke out around 3:30 am on November 18 at a $1.3 million waterfront home in New London, Connecticut, where Hsieh, former CEO of the giant Zappos empire and his brother had been staying

The fire broke out around 3:30 am on November 18 at a $1.3 million waterfront home in New London, Connecticut, where Hsieh, former CEO of the giant Zappos empire and his brother had been staying 

He also started to starve himself and his weight had plummeted to below 100 lb.

Scott Roeben told DailyMail.com, Hsieh’s life in his final months was a cross between Howard Hughes and a cult leader. 

‘He went down the same rabbit hole as Hughes and truly lost his way,’ he said.

‘His life changed over the years. When he started his drinking and drug use were perceived as fun and upbeat, but that all changed when he moved to Utah where it got much darker.

‘But he had built a cult around him — he paid people to be around him and there was no incentive to tell him to stop because he would put people on time-out and ice them out of his life. So the gravy train would come to an end for anyone who tried to stop him.

‘Some of them deserve to be on the hook for what happened to him, because they had a vested interest in keeping it going,’ added Roeben. 

‘They were probably concerned when he was alive, but more than that they were self-interested.

‘Now they have to grapple with the fact that they have uprooted their lives and gone to live in Utah and now they have no money coming in.’


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