What started as an aggressive South Side apartment play has turned into a slow-motion legal pileup for real estate investors Tyler DeRoo, Andy Oshay, and Stephen Lee. The trio is now entangled in a widening feud as lawsuits, foreclosures, and creditor claims stack up around a cluster of Chicago multifamily buildings. One attorney warned, “The walls are caving in on him,” while disputed ownership, unpaid bills, and liens complicate any attempt to steady the portfolio. At this point, tenants, lenders, and would-be buyers are paying closer attention to court dockets than to construction schedules.
As reported by The Real Deal, the partners have been hit with dozens of lawsuits since 2022 that together seek roughly $38 million, and West Palm Beach investor Oshay has funneled at least $32 million into the group’s South Side acquisitions. The disputes range from foreclosure cases to contractor and supplier claims. In one suit, a court ordered DeRoo’s Catalyst Realty to pay about $194,000 for unpaid construction materials. Oshay’s filings accuse DeRoo and Lee of commingling revenues and diverting money into companies they control, allegations that triggered counterclaims and a wave of mechanics liens.
Receivership Ties And A Lingering Equity Build Settlement
Hovering over all of this is DeRoo’s prior role at EquityBuild, the outfit at the center of a federal SEC receivership. Records in that receivership describe a $325,000 settlement tied to DeRoo, and the court-appointed receiver later pursued unpaid installments and related collections in follow-up filings. For readers who want to dig into the legal backstory, the receiver’s disclosures and supporting materials appear in the court record and the federal case summary on RDAPLaw.net and in the appellate summary on Justia.
How The Partnership Unraveled
Oshay’s Delaware lawsuit and the cases that followed led to a May 2023 settlement that let his Alpine Hill platform cut DeLee Development and Catalyst Realty out of operating key assets, according to earlier reporting. That shake-up, along with later transfers and property sales to outside buyers, set off a run of disputed management moves that creditors say sped up loan defaults and pushed off maintenance. The Real Deal previously detailed the lawsuits, management battles and early court skirmishes that previewed today’s heavier wave of filings.
Foreclosures, Liens And Personal Exposure
Wilmington Trust has filed foreclosure cases tied to loans on properties associated with the group, and reporting shows the bank claimed DeRoo stopped making payments in November 2024 on a $2.1 million mortgage tied to his Bannockburn home. Public records and court filings indicate the Bannockburn property is already burdened with junior mortgages and a small state tax lien, while several South Side buildings linked to the investors have drawn building code violations or landed in receivership. Those layers of debt and oversight make it more likely that creditors will push for sales or additional receivership measures before any partner can attempt a clean operational reset.
Legal Risks And What To Watch…