Joseph Chetrit is grappling with health troubles as he and his brother Meyer Chetrit wrestle with financial issues that the developers claim have drained their bank accounts. 

The two brothers, who head the Chetrit Group, were subpoenaed earlier this year, forcing them to discuss their crumbling real estate empire with their lenders' attorneys. The duo once owned nearly $1B in real estate, primarily in New York, according to testimony.

The depositions have been made public in court, but the potential of a trial has been complicated by Joseph Chetrit’s health. 

The 68-year-old was hospitalized in April 2025 after experiencing two strokes, according to three doctors' memos filed in court. In February, he had hip replacement surgery that caused a wound infection, requiring a return to the operating room. He is continuing to recover, according to a March 27 memo. 

In an April 29 deposition, Joseph Chetrit said he was in a coma following the strokes, making it difficult for him to answer questions on his real estate portfolio.

“I have a different priority right now in my life,” Joseph Chetrit said. “My health.” 

Meyer Chetrit testified on March 24 that the Chetrit Group has run out of funds and stopped doing business. He valued the portfolio, which stood at approximately $964M at the end of 2022, at negative $80M. 

When asked how he came up with that value, he said he did the calculation on “a piece of paper, a small piece of paper to myself.”

“When I finish, I put it in the garbage because I don’t want … my wife to be unhappy all day and all night,” Meyer Chetrit said. 

The Chetrit Group has been caught in a flurry of litigation, which mainly revolves around hundreds of millions of dollars in debt defaults. Beyond that, the brothers were indicted by Manhattan District Attorney Alvin Bragg last year and charged with aggravated tenant harassment, a felony.

They were also sued by the city over conditions at the Hotel Carter. The Times Square property had been issued more than 150 violations and was decried by prosecutors as a “public nuisance.” It was scheduled to be sold at auction in May.

The Hotel Carter is also the subject of the lawsuit for which the Chetrits were deposed. The case was filed by lender Mack Real Estate Group in September 2024, alleging that the firm had defaulted on a $31.5M mezzanine loan secured by the hotel at 250 W. 43rd St.

The family's issues seem to have spiraled following the death of their brother Jacob Chetrit in January 2025. He led the Chetrit Organization, a separate company, alongside the fourth brother, Juda Chetrit. 

During the questioning, Meyer Chetrit listed several properties that the firm has lost to foreclosure or sale. Among those in New York City are the Hotel Carter, the former Cabrini Medical Center at 227 E. 19th St., 64-11 Queens Blvd. and 540 W. 38th St. Those in New Jersey include The Pennington and the Fort Lee Executive Park.

“Bye-bye,” he said after naming various addresses. 

He added that his son sold his bitcoin investment and kept the money. Meyer Chetrit bought “one bitcoin” for an estimated $3K, and it sold for as much as $80K. 

Meyer Chetrit was also asked why he continues to go into the office every day, despite not working on any real estate transactions. 

“I cannot stay home with my wife. I prefer to go to sleep,” Meyer said. “I sleep in my office.” 

Meyer was deposed again on April 28, when he explained that his day consists of going into the office, ordering coffee and a piece of cake. It costs him $9.99. An employee — whom he is unable to pay — gives him the money.

“I tell, ‘Tomorrow I give,’ and they know I won’t give it back to them,” he said.

He said that the Chetrit Group is “in the process of being dissolved,” but when asked who is making efforts to dissolve the entity, he replied “Nobody, alone, the air.”

“There is no money, so we stay open for what?” he said.

Even though they haven't been paid for months, he said a handful of employees continue to show up of their own goodwill. 

“God will give me a new life, and I will start to make money,” Meyer Chetrit said.

When asked for comment, attorney Leo Jacobs, who is representing the Chetrits, pointed to his response to Crain’s New York Business. The publication first reported the deposition filings.

Jacobs declined to provide additional statements regarding Joseph Chetrit’s health. 

“When the tide [falls], we will see in real estate who is the last man standing,” Jacobs told Crain’s. “It’s not about being the richest or having the tallest tower. It’s about being the fittest financially.”