Trinity Flood Fighting to Keep Chicago Apartments ICE Raided

Landlord Trinity Flood is fighting to hang onto the South Shore apartment complex federal authorities raided last fall by trying to fend off her lender’s foreclosure, even after a judge appointed a receiver to take over the building and ordered remaining tenants to move out due to dangerous living conditions.

The Wisconsin-based investor’s latest legal maneuvers add to a growing history of tense litigation she has brought in the past eight years against multiple people she has worked alongside and negotiated with in the real estate industry, including her own immediate Flood family members who have decades of investment experience in the mobile homes sector, The Real Deal has learned.

Flood’s 130-unit Chicago property at 7500 South South Shore Drive made international headlines in October when Immigration and Customs Enforcement officers and other federal agencies led a military-style raid on the property, descending from helicopters and emerging from unmarked cars to detain migrants living in the building. Tenants at the time said that agents detained nearly every person in the building, including U.S. citizens, during the raid. Some were released while others were sent to immigration detention.

Legal experts have since questioned whether the raid violated federal search and seizure laws and the state of Illinois opened an investigation into whether or not the Wisconsin-based landlord or the property management company she hired, Chicago-based Strength in Management, tipped off ICE.

The probe centers on claims that Flood or the property management company requested the raid to coerce Black and Hispanic residents — including U.S. citizens — into moving out, which could constitute a violation of state housing discrimination laws. The state opened the investigation last month and it is still ongoing.

Trouble at the South Shore Drive property began escalating in 2024 when Flood stopped hiring security, squatters began occupying empty units and criminal activity ticked up within the building. It’s unclear, however, if any of the crimes that took place at the property can be tied back to the detained migrants specifically. Federal prosecutors haven’t filed any criminal charges against anyone who was arrested during the raid, ProPublica reported last week.

Meanwhile, Flood has been fighting a foreclosure lawsuit filed by Wells Fargo, which is serving as the trustee for bondholders of a $27 million commercial mortgage-backed securities loan tied to 7500 South South Shore Drive as well as two other multifamily properties in Chicago, three in Georgia and one in Arizona. Wells Fargo filed three separate foreclosure lawsuits in each state to address Flood’s default on the loan, which occurred several months before the raid.

The Georgia and Arizona cases are much further along in the foreclosure process. The three Georgia properties were auctioned off in November and are now owned by Wells Fargo entities, CMBS loan tracking service Morningstar Credit reported last month. An auction date for the Arizona property is in the process of being scheduled, according to Morningstar.

But Flood is battling in court to maintain control of her remaining three properties in Chicago. She and her attorney didn’t respond to requests for comment.

In a motion filed in Cook County Circuit Court last week, Flood doubled down on the argument that a lender-placed insurance policy on her three Chicago buildings dramatically increased her operating costs and led her to default on her loan payments.

Flood claims that in 2023, she was paying $93,000 a year to insure the three South Side buildings. In 2024, Wells Fargo’s loan servicer required Flood to take out a new policy that cost over $100,000 per month, resulting in a 977 percent increase to Flood’s insurance costs for the buildings. The plan was based on artificially inflated property values, she claims.

Wells Fargo, however, alleges that the insurance costs are appropriate and that loan servicer K-Star had to issue lender-placed insurance for the properties because Flood had allowed her coverage to lapse and failed to secure a new policy.

Wells Fargo is also pushing to get a receiver appointed to the other two apartment buildings in Flood’s Chicago portfolio at 6916 South Clyde Avenue and 7038 South Chappel Avenue, a new filing submitted last week shows. Representatives of Wells Fargo and its attorney didn’t respond to requests for comment.

The other two Chicago properties haven’t drawn as much scrutiny as the South Shore Drive building but have faced building code violations. A fire at the Clyde Avenue property in 2021 injured four people including a Chicago firefighter.

Flood’s efforts to hang onto the trio of Chicago buildings despite legal headwinds follows a pattern of aggressive tactics she has deployed to establish her career in real estate.

Family drama

Prior to Flood’s purchase of the South Side buildings, people familiar with the deal said she wasn’t well-known among industry insiders in Chicago.

But a 2018 lawsuit filed in Wisconsin lends context to her real estate background.

About a year before Flood bought the Chicago, Georgia and Arizona properties, a Neenah, Wisconsin-based woman with the same name had a contentious falling out with her brother and father, court records show.

Sources familiar with the situation confirmed that the woman who filed the Wisconsin lawsuit is the same person who bought the Chicago, Georgia and Arizona properties. Documents related to the purchase and the family legal dispute both list Trinity Flood as a resident of Neenah, Wisconsin, a town with a population of about 27,000 people, according to the U.S. Census.

Trinity Flood sued her father, Mark Flood, and brother, Eric Flood, in 2018 over a series of business-related disputes tied to their third-generation mobile home business in Wisconsin, called Flood Homes, legal filings show. Mark Flood and Eric Flood as well as their attorneys didn’t respond to requests for comment.

Trinity Flood claimed at the time she was wrongfully terminated from Flood Homes by Mark Flood “without any prior notice,” and that she was told she “cannot have contact with Flood Homes Inc., employees.”

In her lawsuit, Trinity Flood asked a Wisconsin judge to dissolve several LLCs in which she shared ownership with Mark and Eric Flood and to oversee the liquidation of assets held by the shared LLCs. She alleged that under one of the entities, Mark was in default on a commercial loan, which justified the dissolution of the entity.

But attorneys for both Eric Flood and Mark Flood fired back, alleging that Trinity was “asked to avoid interactions with employees of Flood Homes, Inc. as certain employees had complained of [Trinity’s] oppressive and harassing treatment, raising potential liability issues.”

Mark Flood alleged that Trinity Flood filed the lawsuit “in bad faith and for self-interested motives in an attempt to break up the family business which has been in operation for more than 65 years,” and that she is “attempting to force Mark Flood and Eric Flood to sell their personal interests in the business to satisfy her own selfish motives.”

He also claimed that Trinity Flood “has taken steps to secretly market the Flood businesses for sale with brokers, including those in business entities in which she has no controlling interest … and “wrongfully interfered or attempted to interfere with the relationship between Mark and Eric Flood” and third parties, including key lenders and service providers.

In his response, Eric Flood’s attorneys added that he was more qualified to oversee business operations than Trinity Flood, and prior to the lawsuit she had tried to sabotage their shared business efforts by “interfering with lenders and loans” not related to the LLCs named in the lawsuit, and by “intentionally over-leveraging the legal entities with the intentions to depreciate the value.”

“Trinity Flood has refused to make decisions and/or has engaged in actions or inaction that place business operations and business relationships and the personal investments of Mark Flood and Eric Flood at risk,” Eric Flood’s filing stated.

The case was settled with an out-of-court agreement in January 2019.

Other legal strategies

About a year after the dust settled with Eric and Mark Flood, Trinity Flood assembled a portfolio of apartment buildings in Chicago, Georgia and Arizona. A loan backed by the seven properties was packaged together in a $25 million CMBS offering.

Shortly after she bought the Chicago properties, she filed a lawsuit accusing 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’s values. For the three South Side properties, she had paid $18 million.

In the suit, 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 three-building Chicago 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.

By then, Flood was racking up significant city code violations on the South Side buildings. She has been issued fines for Clyde and Chappel Avenue properties and a lis pendens foreclosure that the city filed against Flood regarding code violations at the South Shore Drive property is still pending as the case plays out in court.