At the party in Ibiza, Alex Sapir looked happy.
It was six months before he and his girlfriend, Leila Ben Khalifa, welcomed their daughter, and they were surrounded by their friends, models and Burning Man enthusiasts in fringe and crowns.
From appearances, the question of his dwindling real estate portfolio was not on Sapir’s mind that night in July of 2023. In a photo since removed from her Instagram carousel, Ben Khalifa is grinning, her head turned toward Sapir. He wears a block-printed cardigan tunic and a smile more mild than hers.
“My heart is full of joy and gratitude remembering this magical night,” Ben Khalifa posted when she shared images of the event a month later.
Sapir had been dealing with problems for years. These included a divorce from his wife, Yanina (initiated three years earlier, and ongoing), as well as tax liabilities and family feuds in the business he inherited from his father, Tamir Sapir, a Georgian immigrant who’d famously gone from driving a cab to owning Manhattan properties like 11 Madison Avenue, 100 Church Street and 50 Murray Street.
But at the time of the party, the scion seemed to be on a new path, living between Paris with Ben Khalifa and Miami, where he had a successful project in Arte Surfside, a luxury boutique condo development. Early comers Ivanka Trump and Jared Kushner had helped draw buyers, and all the units were sold. In New York, he had a long-term tenant at 2 Broadway, an office building his father bought in 1995 that is leased to the Metropolitan Transit Authority until 2048.
Yet issues started mounting again, personally and with the properties. He is now selling off three of his last remaining properties in New York and South Florida, suggesting that under his leadership, the family’s property play may no longer be a generational one.
Sapir declined to be interviewed for this story and only provided a brief statement through a spokesperson. He is still dealing with his contentious divorce, and sources say he split with Ben Khalifa, who has edited her Instagram page in what appears to be an attempt to downplay their relationship: altering captions and removing some images of him.
Two of the properties — the Nomo Soho at 9 Crosby Street and a development site in Miami — are owned by his troubled company, Sapir Corp, which Israeli bondholders are coming after for $155 million in debt. He’s also parted with one valuable asset, 260 Madison Avenue, which had been owned by the 35-year-old family real estate company, Sapir Organization.
So far he is holding onto the nearby office building at 261 Madison, possibly for a condo conversion.
Hospitality play
Sapir Corp’s unraveling has been years in the making, and the story of its collapse runs straight through the ivy-covered entrance of the Nomo Soho hotel.
Sapir and fashion executive Gerard Guez scooped up the 264-key boutique hotel in 2015 for $200 million at a foreclosure sale, paying a premium for a trophy property in a hot submarket. For a while, the bet looked savvy. By 2017, Israeli stock-exchange filings valued the hotel at $246.3 million. A year later, Sapir bought out most of Guez’s stake, bringing Sapir Corp’s ownership to 99 percent. In 2019, Goldman Sachs provided a $115 million refinancing.
Then the bottom fell out.
Covid hammered the hotel, sending occupancy to 1.9 percent in April 2020 and forcing Sapir to pour in his own capital just to keep operations going. He never invested in upgrades, and the hotel’s condition deteriorated. The valuation dipped to $179 million. Sapir took out an $89 million Israeli bond-market loan in 2022 that replaced the Goldman Sachs mortgage.
Meanwhile, debts mounted and the property continued to bleed cash. Sapir Corp cut management fees and quietly shopped the hotel last year, but never found a buyer.
“They actually injected a huge amount in the company and its assets.”
This summer, the company was scrambling for extensions as debt obligations came due. Sapir agreed to inject $14 million of his own capital to postpone the maturity date. But as the initial July 1 payment approached, Sapir informed bondholders he wouldn’t be able to cover it, triggering a default.
Sapir Corp entered insolvency proceedings, telling a Tel Aviv court that it could no longer meet bond payments or cover basic operating costs. All of its directors resigned, and several trustees are now overseeing the wind-down of the firm, which has just two remaining assets: Nomo Soho and the Miami site, a 1.5-acre assemblage in Edgewater, near Wynwood, which Sapir and his partners relisted in July for $41 million, though Sapir said the asking price was closer to $50 million.
“They actually injected a huge amount in the company and its assets,” Alon Binyamini, one of the trustees overseeing the liquidation, said. “It’s not a typical insolvent company where we see that the controlling shareholder took money from the company. I don’t think this is the case. They were the opposite.”
Sapir Corp placed Nomo Soho into bankruptcy and will run a court-supervised auction of the hotel to pay down the company’s remaining $155 million in debt across two Israeli bond series. It has lined up Israeli hospitality chain Dan Hotels to purchase the property for $125 million. If no higher bidder emerges, Dan will be the new owner of a property once seen as the crown jewel of Sapir’s portfolio.
“Facing the ongoing challenges in the market and slow recovery from two years of Covid, during which the operation was supported with significant equity, we chose to support a process that is the most likely to result in the full payment of the debt to the bond holders,” a Sapir spokesperson said.
The liquidation may not be the end of the saga. The bondholders can still go after Sapir personally for the $14 million he promised them.
Twin trophies
A few blocks south of Grand Central, 260 and 261 Madison Avenue flank the street like walls of a glass-and-metal canyon. The pair of 1950s-era buildings were trophy holdings of the Sapir empire for nearly three decades, though the company struggled on and off with its 1 million square feet of office space.
Alex is now parting ways with half the pair. Tamir bought both in 1997.
The Sapir Organization in October struck a deal to sell the 22-story, 570,000-square-foot 260 Madison Avenue to Jonathan Bennett’s AmTrustRE for $270 million.
Sapir will hold onto 261 Madison — the taller of the two, with a more pronounced, set-back tower section.
At 261, a strap lifting a heavy heating and air conditioning unit in 2015 snapped and damaged the building, which caused the property’s CMBS loan to be watchlisted by its servicer. The loan was flagged again in 2019 due to increasing operating expenses caused by climbing real estate taxes and repair-and-maintenance costs.
It was watchlisted one last time in 2022 ahead of its June maturity date. Sapir refinanced the properties at the end of the year with a $326 million loan from JPMorgan Chase and Mack Real Estate Group.
The law firm McLaughlin & Stern and the executive Solomon-Page Group lease 260 Madison, and 261 is where the Sapir Organization has its office.
But there have been challenges with other tenants.
The short-term office provider Knotel (which Sapir had invested in as part of a $70 million funding round in 2018) took 45,000 square feet at 261 Madison Avenue through a management deal that year. But Knotel filed for bankruptcy in 2021, and it’s not clear what’s come of the space.
WeWork also signed a lease in the building for 44,000 square feet in 2012, but by 2021 Sapir claimed the company stopped paying its rent. Sapir sued the co-working firm and its controversial co-founder Adam Neumann for $17 million, saying he only learned that WeWork planned to walk away from its lease when he read about it in The Real Deal.
The 261 Madison location was one of the leases WeWork rejected when it went through its own bankruptcy in 2023, and the two sides settled their lawsuit this past September. The space is now occupied by Industrious.
The building, 28 stories and 384,000 square feet, is the one sources said the company may convert into residential condos, although no plans have been finalized. Sapir Organization notes on its website that it expects to expand the Arte brand he launched in Surfside, with potential projects in the U.S., Europe and the Middle East, per the company website.
The resort-style, oceanfront Surfside development, a 12-story, 16-unit building where the Trump-Kushners rented an apartment, sold out for a combined $225 million in 2023. While the project was seen as a success, Sapir is still dealing with a lawsuit brought by billionaire buyer Ramzi Musallam alleging construction defects in his penthouse. A trial is set for next summer.
Sapir doesn’t appear to have plans for another Miami project.
Rags and riches
Tamir Sapir was the classic American rags-to-riches story.
A refugee from the former Soviet republic of Georgia, he immigrated to New York in 1976 and scratched out a living as a yellow cab driver before he parlayed his Soviet contacts into lucrative fertilizer and oil contracts and, eventually, invested in real estate.
In 2003 he bought the 30-story Art Deco office tower at 11 Madison Avenue for $675 million, followed by the Duke Semans Mansion on the Upper East Side for $44 million in 2006.
His net worth peaked at $2 billion in 2007. By 2010, when Forbes profiled him, he had fallen off their billionaire’s list and was worth about $700 million, or perhaps less. Alex was already at the helm, and in a lawsuit brought by a Las Vegas partner, he claimed the firm was $250 million in debt.
Tamir seemed to indicate he had stepped back.
“My son is doing the business,” Tamir said in court, per Forbes. “‘Papa, give me money,’ and that’s it. I am the money man. Why am I expected to know so much?”
When Tamir died in 2014, his family was left with a huge tax bill.
Tamir was survived by his first wife, Bella, and their three children, Alex, Ruth and Zina. With his second wife, Elana, he had a daughter, Zita, and a son, Eli, who was born after his death.
The estate paid the Internal Revenue Service $153 million in 2015 and 2018, but late last year Alex filed a lawsuit in federal court seeking a $92 million refund on those payments.
Alex said in the lawsuit that the estate had been unable to claim deductions for several pending claims against it. One of those was a $102 million claim bought by Rotem Rosen, who was married to Zina for 12 years before they divorced in 2019.
Rosen said he was owed money for his role in selling 11 Madison Avenue and Tribeca House, at 50 Murray Street and 53 Park Place.
Sapir and Rosen settled their suit in 2022, and in court papers Alex wrote that the rest of the claims were settled in 2024.
He said the estate had filed for a refund claim in April, but heard nothing from the IRS.
“The Estate is being strained with maturities of its term debt and other cash flow requirements which cannot be addressed until the refund is received,” he wrote. “This imposes a severe hardship on the estate and is causing it financial injury and injury to its reputation and credit rating as a result of the IRS’s unexcused delay.”
“The injuries are increasing daily.”
The case is ongoing. Between the bills, suits, sales and remaining holdings, it is difficult to get an overall financial picture of Sapir Organization.
Life of parties
Throughout, Sapir seemed to find some separation from the drama in the courts and the buildings. He got into hospitality ventures with Rosen; both were part of a group that brought Zuma, a restaurant hotspot in 261 Madison, and the viral “Salt Bae” steakhouse to New York.
He also seemed in his element at Burning Man, where he was affiliated with a group called Monkey Camp. Photos from its account show him there with his wife in 2020. Later, he went with Ben Khalifa, and he’s pictured in a pair of elaborately patterned harem pants, two braids in his beard. He’s often seen wearing layers of necklaces including one that holds his vape.
During the past two years with Ben Khalifa, a model and businesswoman, he attended splashier events: the Met Gala, Cannes Film Festival and Art Basel.
He continues to shed properties. Sapir’s divorce from Yanina is still pending more than three years after she filed, and the estranged couple has one major asset left to sell: their waterfront Venetian Islands estate in Miami Beach, which is asking $38 million.Earlier this year, they sold their adjacent waterfront home on the Venetians to Shark Tank investor Rohan Oza for $9.8 million. The 60,000-square-foot home on 8 acres on the waterfront in Great Neck’s King Point owned by his father has also been on the market, listed for as high as $100 million, though more recently for $45 million.
Partying and personal trouble don’t disqualify anyone from real estate, and without Sapir’s responses, it’s hard to know where his luck ran out and where his skill, or drive, didn’t pick up.
But according to his spokesperson, the family business — Sapir Organization — isn’t going away, despite the troubles with Sapir Corp.
“Given that Sapir Corp was focused on a few assets for some of the Sapir family members and never owned by the Sapir Organization or part of its legal structure, Sapir Organization will continue operations as it always has for 3.5 decades,” the Sapir spokesperson said.
