In a tumultuous period for Chicago’s multifamily market, marked by rising interest rates and surging foreclosures, one landlord’s ambitious expansion has raised eyebrows.
Yissocher “Izzy” Rotenberg, a real estate investor from Brooklyn’s Borough Park neighborhood, entered a popular online real estate investing forum in January 2023, expressing a keen interest in acquiring more apartment buildings in Chicago’s far south side.
By the end of 2023, Rotenberg, along with his deal partners including Naftalie Berger, had managed to accumulate around 500 apartment units across the Windy City within just two years.
Public records indicate that the duo invested at least $48 million in 25 properties, securing approximately $40 million in loans along the way.
However, lenders soon began circling Rotenberg, as the majority of his properties fell into foreclosure.
Currently, 14 properties associated with Rotenberg and Berger are embroiled in foreclosure lawsuits.
Receivers appointed by the court to manage some of these distressed properties have reported instances of mismanagement at Rotenberg’s buildings.
Notably, at a 22-unit apartment complex located at 7763 S. South Shore Drive, Rotenberg allegedly failed to provide essential rent rolls to the receiver managing the property.
Additionally, at another of his holdings, the 34-unit building at 1901 West Pryor Avenue, roughly 80 percent of the units are reported vacant, further underscoring the struggles of Rotenberg’s portfolio.
To avoid some foreclosures, Rotenberg has turned to selling distressed properties, with Eliazer Tauber emerging as a buyer.
However, Tauber has been linked to suspicious transactions in Chicago, raising red flags among industry professionals.
Rotenberg’s portfolio troubles are compounded by numerous building code violation complaints from the city of Chicago.
City officials have reportedly expressed growing frustration with Rotenberg’s management of his properties, with some insiders claiming, “The city ran him out of town.”
Despite repeated attempts for comment, Rotenberg and his lenders have not responded, with representatives from both Asset Based Lending and Sharestates declining to comment.
Rotenberg’s rapid rise and subsequent fall as a Chicago real estate figure reflects a broader trend involving external investors from New York and New Jersey.
Since around 2017, these investors have been acquiring thousands of units across Chicago’s South and West Side at bargain prices, often cycling properties among themselves and pushing up prices and loans.
By March 2024, Fannie Mae took notice of these practices, blacklisting at least eight investors on allegations they were neglecting essential property maintenance and engaging in dubious transactions.
Though Rotenberg was not included on Fannie Mae’s blacklist, the trajectory of his acquisitions suggests he may be heading down a similar troubling path.
His buying spree began in 2022, coinciding with rising interest rates and tightening lending conditions.
Rotenberg adopted a strategy involving high-interest loans from hard money lenders, which quickly led him into difficulties.
For instance, in July 2022, he purchased an 11-unit building at 7641 South Saginaw Avenue for $737,000, securing a $757,000 loan from Sharestates, which subsequently initiated foreclosure proceedings less than two years later in June 2024.
Remarkably, this property avoided foreclosure when Rotenberg sold it to Tauber for $2 million—a price significantly inflated from the initial sale, despite being in foreclosure.
This wouldn’t be the last time Tauber acquired Rotenberg’s properties at steep markups, further complicating the narrative surrounding these transactions.
The financial logic behind Tauber’s inflated purchases has raised eyebrows among seasoned real estate investors.
Adding to the controversy, involved parties have raised allegations against Rotenberg, with Shlomo Horowitz suing him over ownership disputes.
Horowitz claimed to possess majority interests in both the Saginaw Avenue property and another at 2814 East 78th Street.
Having originally purchased the 78th Street property for $265,000, Rotenberg later sold it to Tauber for $1.1 million shortly after foreclosure proceedings initiated.
Horowitz alleged he received nothing from these transactions, claiming he owned 75 percent of the stakes in the LLCs that executed the sales.
He ultimately secured a $1.9 million judgment against Rotenberg, who failed to engage legal representation in the case.
The dubious financial rationale underlying these property sales further compounds the sense of chaos surrounding Rotenberg’s real estate dealings.
Tenants have also borne the brunt of the situation, grappling with the repercussions of alleged mismanagement.
At an 11-unit property located at 5449 West Quincy Street, tenants reported being without hot water for more than a month.
The appointed receiver managing the building struggled to determine legitimate tenants from illegal squatters due to a lack of documentation provided by Rotenberg.
In a report regarding the Quincy Street property, the receiver noted, “Unfortunately, the receiver was not provided any information or leases; … no rent has been collected.”
With lenders moving to hire brokers to sell distressed properties linked to Rotenberg, the chaos in his portfolio shows no signs of abating.
At the 22-unit building on South Shore Drive, which has suffered from multiple break-ins and has become a shelter for the homeless, the property is now listed for sale at $1.5 million—significantly below the $2.7 million price Rotenberg initially paid in 2023.
This listing highlights the dire condition of the building, which is described as requiring extensive renovations and boasting over 50 percent vacancy.
image source from：https://therealdeal.com/chicago/2025/04/25/inside-izzy-rotenbergs-crumbling-chicago-multifamily-empire/
