Joseph Chetrit and Meyer Chetrit

It was a somber start of the year for the Chetrit family. They mourned the loss of one of their four founding executives, who died at the age of 69.

Jacob Chetrit along with his brothers Joseph, Juda and Meyer formed the Chetrit Group in the 1980s when they began purchasing apartment buildings in the outer boroughs before venturing into a stake in an $841 million deal for Chicago’s Willis Tower (then called the Sears Tower) as well as New York’s Standard Oil Building and, eventually, the Chelsea Hotel. Three decades later, Jacob and Juda split off from their siblings Joseph and Meyer to establish their own organization.

Both firms have found success. These days, Joseph and Meyer Chetrit’s Chetrit Group owns 500 Metropolitan Avenue in Williamsburg, Brooklyn; the American Express Building and 1 Whitehall Street in the Financial District; 545 West 37th Street; and a portfolio of more than 10,000 apartments across several states.

But the Chetrits have been grappling with financial challenges lately, after defaulting on $1.6 billion in debts and seeing eight properties sink into foreclosure.

The Chetrit Group tried to revive Brooklyn Heights’ Hotel Bossert after purchasing it for $81 million in 2013 and getting a $112 million loan, but the property went to a foreclosure auction before Beach Point Capital Management picked it up this February.

They also risk losing two Lower Manhattan office buildings, 1 Whitehall Street and 428 Broadway, after defaulting on $200 million worth of loans. And they defaulted on $223 million in mezzanine loans on the Carter Hotel in Times Square as well as an $8 million mezzanine loan for their two-tower, 1,313-unit apartment complex at 265-275 Cherry Street in Manhattan last year. Fortunately, they secured a refinancing plan with Madison Realty Capital to avoid foreclosure on that property.

The durability of the Chetrit brothers, after all, is itself indicative of a certain power in the marketplace. Plus, they’ve had better luck with retail tenants lately. They lured Lincoln Center stalwart Rosa Mexicano to move from 61 Columbus Circle into the second floor of the Empire Hotel at 1889 Broadway with a 15-year lease.