How Multifamily Missteps Shaped South Side Immigration Raid

Warning signs that Trinity Flood’s Chicago real estate portfolio could land in trouble quickly piled up after the little-known Wisconsin-based investor bought a trio of apartment complexes in 2020.

Although it may not have been obvious five years ago that one of Flood’s South Side buildings would become the site of a massive federal immigration raid and the subject of national controversy, the property’s chaotic backstory illustrates how a transaction gone wrong can devolve into a precarious situation for an entire neighborhood.

Various legal filings reveal that opportunities to address disarray at the property came and went without action from the landlord or Cook County’s court system.

The consequences of that inaction culminated last week when residents woke up in the middle of the night to hundreds of federal agents descending on the building from trucks and helicopters. They arrested dozens and reportedly detained many more tenants, including children, during the operation.

In the aftermath of the raid, local and state officials criticized the tactics and Illinois Governor J.B. Pritzker called on state agencies to investigate if federal agents used excessive force against minors.

The first signal of trouble at the property came from Flood over five years ago, shortly after she purchased the building and two others nearby for $18 million total.

Buyer’s remorse

A few months after buying the apartments in 2020 as part of a 1031 exchange, Flood filed a lawsuit against the seller and brokers involved in the purchase.

Such 1031 deals allow investors to defer taxes on the sale of real estate if they reinvest the proceeds into a new property transaction within certain timelines. So Flood had to move fast.

She purchased the South Shore Drive building as a part of a portfolio that also included 6916 South Clyde Avenue and 7038 South Chappel Avenue.

A few months after buying the properties, Flood accused seller Daniel Hedaya of DAX Real Estate and his brokers, Aaron Sklar and Noah Birk of Chicago-based Kiser Group, of improperly inflating the property values.

Flood called out the conditions of the South Shore Drive property, where the unsettling raid would later take place, including the need for around-the-clock, on-site security that cost $15,000 monthly. She claimed the prior owner didn’t make her aware of the security requirements, and its brokers prevented her from touring more than two of the 130 units in the complex because the building was almost entirely occupied.

Flood pointed out the portfolio had last sold for $11 million in 2017 prior to DAX’s renovations. She alleged the brokers told her the jump in value was due to the improvements and increase in occupancy at the buildings. Hedaya told The Real Deal in 2019 that his firm spent “several million dollars” on the projects.

But at 7500 South Shore, Flood claimed she had been told that all units in the building were renovated when in reality, 21 had been left untouched. She further alleged that the scope of the renovations throughout the building had been exaggerated or misstated.

The parties reached a confidential settlement in October 2023, but by then Flood was racking up significant city code violations on at least two of her three Chicago buildings. Kiser Group’s Sklar declined to comment and Birk didn’t return a request for comment.

City’s suspicions

In August 2021, about a year-and-a-half after Flood purchased the portfolio, a fire broke out at the 6916 Clyde Avenue building, injuring four tenants and a firefighter. As the city began monitoring the building for code violations, it was also tracking similar problems at 7500 South Shore.

Since 2021, the buildings have racked up dozens of code violations, most of which are associated with the South Shore Drive building.

While conditions continued to deteriorate, Flood attempted to sell the portfolio last year but never closed a deal.

Issues documented as recently as this summer at the South Shore Drive property include “inoperable elevators, flooding, stench of urine in the stairways, and armed occupants along with alleged criminal activity and shootings at the property,” an email from the city legal department stated.

The email, which was sent in August, went on to note that the city hadn’t conducted a full interior inspection of the property due to security concerns and a shooting that took place on June 23 during an inspection.

When Flood failed to resolve the issues, Chicago officials requested in August that Cook County Circuit Court Judge Leonard Murray appoint a limited receiver for the building to help kickstart work on the property. The request is still pending in court.

Getting a receiver appointed to a building can be a lengthy process, even in cases where a building is in dire condition, said Eric Janssen, a receiver and founder of Chicago Real Estate Resources.

“Sometimes it takes a while for both sides to go back and forth and for a receiver to be ultimately appointed,” Janssen said. “And each judge is different.”

In the meantime, the portfolio began to run into financial trouble, as well.

Lender closes in

As the code violations accumulated, Flood was hit with a $27 million foreclosure lawsuit in April 2025, alleging she was behind on loan payments and had failed to insure the South Shore Drive building.

In addition to the South Side portfolio that Flood bought for $18 million, the investor also purchased three properties in Georgia and one in Arizona with a $25.3 million loan. The loans against all six properties were later packaged up with other real estate debt and sold off to commercial mortgage-backed securities investors. Now, Flood is in danger of losing all 354 units across the nation, including the 208 in Chicago’s South Shore neighborhood.

Rather than forfeit the struggling properties via foreclosure, Flood fought back, seeking to retain her control.

Amid the legal-back-and-forth, Wells Fargo, which was representing the trustees of the debt package, repeatedly requested that a judge appoint a receiver to the South Shore Drive property. Flood successfully delayed such an appointment multiple times.

The debate was raging just days before the raid.

A recent legal filing from Wells Fargo stated that the lender first requested the appointment of a receiver in May. After Flood’s resistance, Wells Fargo went on to state that “now, four months later, the condition of the South Shore Property is worse than before and the appointment of a receiver has become urgent.”

Wells Fargo filed an emergency motion on September 22 requesting, once again, that Cook County Circuit Court Judge Debra Seaton appoint a receiver.

Flood hit back, stating that an ongoing dispute over a lender-placed insurance plan needed to be resolved first.

Eight days later, federal agents stormed the building, ultimately arresting 37 people who were “believed to be involved in drug trafficking and distribution, weapons crimes, and immigration violators,” according to a statement from the U.S. Department of Homeland Security. Further information on the severity of the alleged crimes has been limited so far.

Illinois and Chicago officials have also alleged the agents infringed on the rights of other tenants in the building who were detained outside and who may have suffered from lost or damaged property.

It’s unclear how the property got onto the federal government’s radar but Chicago officials said they didn’t know about the raid ahead of time or collaborate with federal law enforcement agencies on the operation.

The day after the raid, Seaton agreed to appoint a receiver to the property at an Oct. 17 court hearing. She hasn’t yet determined who the receiver will be despite Wells Fargo putting forth several specific options throughout the legal process.