By September, it seemed like things couldn’t possibly get worse at 7500 South South Shore Drive.
A little-known real estate investor from Wisconsin named Trinity Flood bought the Chicago apartment building in 2020. As an out-of-state-investor, it’s not clear how much she knew about South Shore, the building’s neighborhood, which skirts Lake Michigan and extends west to I-90. Transportation access, unique 1920s apartment buildings, side streets lined with single-family homes and the forthcoming Obama Presidential Library all lend to South Shore’s appeal.
But it’s farther south than buzzier South Side neighborhoods like Bronzeville and Hyde Park and the neighborhood still struggles with the remnants of decades of redlining and disinvestment. As of October, South Shore had the highest number of homicides in the city over the past 12 months, according to neighborhood-level data compiled by a local ABC affiliate. Both Hyde Park and Kenwood, immediately north of the neighborhood, have had zero homicides in the past year. To successfully invest in Chicago, in other words, landlords need to know neighborhood and even block-level nuances.
At 7500 South Shore, it soon became apparent that Flood was not prepared.
Since 2020, the property’s conditions have deteriorated significantly. Elevators are broken, sewage gases are leaking through the building and the city’s legal department recently documented “armed occupants along with alleged criminal activity and shootings at the property.”
Wells Fargo, on behalf of CMBS bond holders, filed a $27 million foreclosure lawsuit in April for delinquent payments on a loan backed by the South Side property as well as several others in Chicago, Georgia and Arizona.
Rather than quietly admitting defeat and handing her keys back to the lender, Flood responded by clinging to the properties via extensive litigation. Recent filings hone in on Flood’s inability to find an insurer for the building and struggling with the costs of a lender-placed policy.
Now, her attempts to hang onto control of the apartments as long as possible have snowballed into a worst-case scenario few could have imagined five years ago.
On the night of Sept. 30, hundreds of federal agents raided Flood’s South Shore Drive building in an event that yielded national attention.
Videos taken by neighbors show agents descending on the five-story brick building in helicopters, while trucks and the inconspicuous vehicles favored by Immigration and Customs Enforcement ferry in hundreds of others. ICE Chief Gregory Bovino charged in, tailed by a News Nation camera crew invited to follow the operation. Many tenants were reportedly detained outside for hours, before being released back into the building.
The operation, a combined undertaking of the FBI, ATF and Customs and Border Protection, yielded 37 arrests. Some arrested were “believed to be involved in drug trafficking and distribution, weapons crimes, and immigration violators,” according to The Department of Homeland Security.
“This raid was really unlike anything that I have witnessed, either as a lawyer or as a law professor,” Hugh Mundy, a law professor at The University of Illinois Chicago who specializes in criminal procedure, said.
Making the building’s downfall even more stunning, 7500 South Shore had undergone a multimillion-dollar renovation shortly before Flood purchased it and was, according to brokers, nearly 100 percent occupied at the time.
Though most multifamily purchases won’t end up this poorly maintained or the target of a federal raid, 7500 South Shore’s undoing still serves as a cautionary tale of how neglect can lead to financial distress, especially when a property ends up in the crosshairs of President Donald Trump’s ramp-up of federal policing powers.
In that sense, Flood’s property is far from the only one facing precarious circumstances. As of October, lenders in the U.S. have already 50 percent more multifamily foreclosures than they did in all of 2020, according to data from ATTOM Real Estate Solutions.
Buyer beware
In January 2018, New York-based Dax Real estate paid just under $11.5 million for three complexes with 208 combined units at 7500 South South Shore Drive, 6916 South Clyde Avenue and 7038 South Chappel Avenue, according to Cook County property records.
The South Shore Drive property was “very rundown and substantially vacant,” managing partner Daniel Hedaya told The Real Deal in 2019. DAX spent several million dollars on renovations to the building, he said.
In the spring of 2019, DAX went to sell the properties for $20 million, marketing the area as “one of the most appreciating pockets of the South Side,” according to Aaron Sklar, one of the Kiser Group brokers who had the listing. Flood closed in early 2020, paying 60 percent more than DAX had spent two years earlier.
But she was unsatisfied with her purchase.
Shortly after buying the apartments, Flood filed a lawsuit alleging Hedaya and his brokers, Sklar and Noah Birk of Kiser, had improperly inflated the properties’ values.
Squatters began to take up residence in the building, and city inspectors reported that the property manager was no longer able to “re-assert control over the building.”
The building needed around-the-clock, on-site security that cost $15,000 monthly, she said. The seller had not made 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.
But in a legal response, Hedaya’s attorney noted that Flood had assigned an intermediary to review details of the purchase and wanted to close quickly because she was trying to execute a 1031 exchange.
“[Flood] seek[s] only to complain about the outcome of [her] own actions — committing to a deal before undertaking the expansive due diligence to which they were entitled,” the response reads.
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. Sklar and Birk declined to comment.
In August 2021, about a year and a half after Flood purchased the portfolio, a fire broke out at her Clyde Avenue property, one of the other South Side buildings in her portfolio. The blaze injured four tenants and a firefighter. The city began monitoring it for code violations, and inspectors also tracked similar problems at 7500 South Shore.
Since then, the buildings racked up dozens of code violations, most associated with the South Shore Drive building.
The slow deterioration soon accelerated.
In 2022, under a rental assistance program established by the state of Illinois, some migrants moved into the property, though it’s unclear how many. Tenants generally didn’t report concerns with them besides an increase in trash in the hallways, according to Jonah Karsh, an organizer with the Metropolitan Tenants Organization who had helped form a tenants union at the building in 2024.
The turning point, Karsh said, was when a new property manager, Strength in Management, took over in early 2024. Soon after, Flood stopped providing security services, and maintenance issues went unaddressed.
Flood and Strength in Management did not respond to requests for comment.
Squatters began to take up residence in the building, and city inspectors reported that the property manager was no longer able to “re-assert control over the building.”
Flood attempted to sell the portfolio around the same time but never closed a deal.
In a code violation case still pending in court, city officials this summer requested that a judge appoint a limited receiver to the property. Wells Fargo also requested that a judge issue a receiver to the property as part of its foreclosure proceedings which kicked off in April.
On Sept. 30, just one day before a judge was scheduled to hear Wells Fargo’s argument for receivership, federal agents swarmed in for the raid.
There is some speculation that Flood or Corey Oliver, who owns Strength in Management, tipped off federal agents about the presence of migrants and illegal activity in the building. Agents carried out the raid with the consent of the owner, according to the New York Times.
A map found at the property shortly after the raid and photographed by a Chicago Sun Times reporter included labels for units with migrants and squatters.
“Whoever tipped off ICE about that level of detail about who’s in what unit in the building has to have had knowledge of that,” Karsh said. “The most obvious answer to that would be Strength in Management or Trinity Flood.”
City officials, who were also familiar with conditions at the property, denied any collaboration with federal authorities ahead of the raid.
For Flood, the aftermath of the raid plunged the reputation of her South Shore Drive property to a new low — but it also meant she had evaded receivership for just a bit longer.
Expect the unexpected
Not long after Flood bought the South Shore Drive building in early 2020, interest rates took a historic plunge, spurring a boom of investment and new development in many U.S. cities.
But when rates rose again soon after, buyers who made risky purchases in 2020 and 2022 found themselves in a losing battle. Inexperienced investors and syndicators have gotten hit with foreclosure filings, and mortgage fraud that took place during the frothy period has begun to threaten the stability of some regional banks.
Since the beginning of the year, lenders have filed 11,300 multifamily foreclosure complaints, compared to 7,500 in all of 2020, ATTOM found.
Whether problems at other struggling properties across the U.S. would make federal raids a serious risk is unclear, especially since the massive operation on South Shore Drive defied long-established norms of search and seizure, legal experts said.
Lenders in the U.S. had 50 percent more multifamily foreclosures in the first nine months of 2025 as they did in all of 2020.
“You would normally expect that kind of force to result in more arrests for more serious crimes,” Mundy, the law professor, said, calling the scale of the raid more fitting for a racketeering investigation.
He added that a warrant typically targets specific units rather than an entire building. TRD requested copies of warrants and arrest records from the federal agencies involved in the raid but has not gotten a response.
Even before the raid, federal agents were challenging conventions of immigration enforcement across the city.
A U.S. district judge in Chicago recently ruled that federal immigration agents illegally arrested 26 people in Chicago without warrants in January, violating a consent decree that dictates how such arrests can be carried out.
Landlord groups like the National Apartment Association have put together guidance on how to respond to subpoenas and raids. Property managers are not required to allow ICE agents to enter a building, they advise, unless they have a criminal warrant signed by a judge. Owners can consult with attorneys before responding to a subpoena for information about tenants.
Once law enforcement agencies enter a property, however, landlords have little influence over how a raid is conducted.
“The bottom line is, there is not much a landlord can do as it relates to police conduct within their building, whether in a common area or a tenant’s apartment,” Monu Bedi, a DePaul University College of Law Professor who specializes in criminal procedure and military law, said. “If there is damage to the building, landlords are able to recover money for the property but that is different than their rights to prevent officers from entering.”
The fallout
When the dust settled in the weeks after the raid, just 35 paying tenants were left living in the 130-unit building, along with about 10 squatters, Oliver, the property manager, told Cook County Circuit Court Judge Debra Seaton Oct. 17.
Karsh estimates that a majority would like to move out if given financial assistance.
The building remains on insecure footing, both in terms of safety and finances.
Inspectors tasked with evaluating electrical systems at the building were alarmed by faulty wiring leading out to the city’s utility poles, noting that lines hang low enough for a live wire to hit the top of a garbage truck, they said at a recent hearing.
They also pointed to fire hazards caused by extension cords and hijacked meters in the building, likely used to provide power to squatters’ units. Only one of the building’s elevators is operating — still. A plumbing inspector noted that the boiler room had a strong odor that could be attributed to a gas leak and stated that raw sewage and sewer gases were leaking into the building.
But Oliver said that since the raid, Flood had invested $100,000 into repairs to the building, including plumbing and electrical repairs. He also said he was told he needed to re-submit a permit for some of the electrical work that needed to be done at the property.
Three armed security guards are another new addition. They now patrol the building from 6 p.m. to 6 a.m. every night.
Oliver asked Judge Debra Seaton what he should tell Flood if the recommended repairs are more costly than she expects. Flood never appeared at the hearing, her attorney attending on her behalf.
“There shouldn’t be an issue if she wants to keep this out of a receivership,” Seaton said. “Your owner could have been present for his hearing today and she is represented by legal counsel.”
Seaton said she will not appoint a receiver until she can evaluate the progress of the work at the property. If the immediate dangers are not resolved quickly, she said she will not only consider appointing a receiver but will also weigh issuing a court order for all the remaining tenants to relocate, likely with relocation assistance.
Things might not turn around so easily, Alderman Greg Mitchell, who represents the area, believes. That worries him.
“My current concern is that I still don’t feel the building is safe,” he said.