Troubled South Side Investor Hit by More Foreclosure Suits

Embattled South Side home flipper Chris Urban clapped back against the storm of foreclosures surrounding dozens of his properties in legal filings this month, as more lenders took him to court over unpaid debts.

Urban and his sister, Aneta Urban, have been named in a growing number of foreclosures and lawsuits related to a portfolio of dozens of properties across Chicago’s South Side and south suburbs that started to buckle under the weight of unpaid debts in 2024. The pair borrowed money from fellow investors in a real estate training program run by Andrew Holmes, who is also suing them for fraud.

In filings across several lawsuits in January, the Urbans argued their lenders failed to credit payments received, either directly or indirectly, to reduce the amount the Urbans owed the lenders. The filings argue the amount the Urbans owe should be offset by any money the lenders received from selling any collateral or other payments from the Urbans.

Although the Urbans didn’t provide proof of payments to the lenders, they denied the amount that the lenders claim is owed and demanded “strict proof” of the accounting in the filings.

The argument reflects the precarious financing of the Urbans’ portfolio. As financial troubles mounted in 2024 and 2025, Chris Urban used short sales to give lenders partial payments while using other properties as collateral for unpaid debts, The Real Deal previously reported. In other cases, Urban would sell a home from one LLC to another he operates, satisfying one mortgage while taking out another for the purchase, property records show.

The defense comes as the Urbans are facing foreclosures on more than 80 properties between lender Renovo Financial and a handful of private lenders, amounting to millions in debt. While some lawsuits from early last year have been resolved, foreclosure suits continued to pile up late last year.

Meanwhile, business loan company OnDeck Capital brought a third lawsuit for unpaid debt against one of Urban’s LLCs in November. American Express also filed a lawsuit against the same LLC, and a separate one against Chris Urban personally, alleging he defaulted on debt, in January.

Chris Urban declined to comment, saying he would resolve the disputes “through the courts, not the media.”

New foreclosure

Since mid-October, lenders have brought two more lawsuits against the Urbans for alleged unpaid debts. In both cases, the Urbans filed the same defenses, arguing the lenders did not credit any repayment they had received to the loan balance.

In October, Shirley Pollock, through her LLC Best Funding Solutions, filed to foreclose on five properties in Chicago and Calumet Park where she loaned the Urbans money. Pollock’s lawsuit claims the combined unpaid debt, including late fees, amounts to more than $1 million across the five properties.

At three of those homes, the Urbans took out second mortgages between $50,000 and $65,000 with two other lenders — Homes by MB and Misener Wealth Builder — that are also named as defendants.

It’s the second foreclosure suit from Pollock, following a lawsuit earlier that same month alleging unpaid debts of almost $500,000 across three properties.

She is also named as a defendant in the lawsuit brought by Holmes and his business partner, Mary DeSloover, alleging fraud. That lawsuit argues Pollock aided the Urbans in covering up their financial pitfalls as they took on more debt from other investors. Pollock has denied the charge and said she is also a victim of the Urbans in legal filings.

Pollock did not respond to a request for comment.

Olmos Private Equity

Another lender, Edmund Olmos, is also moving to seize two of Chris Urban’s properties through foreclosure.

Through his LLC, Olmos Private Equity, Olmos issued Urban a $150,000 mortgage for a home on Burley Avenue and $236,000 for a home on 88th street in 2023 and 2024. The lawsuit alleges Urban failed to pay back the loans when they matured, and the balance has grown to more than $468,000.

Urban took out a second mortgage at both those properties, records show. Olmos issued mortgages to the Urbans on more than a dozen properties between 2023 and 2024, often as second mortgages, property records show.

Mitchell Lieberman, an attorney for Olmos Private Equity and other investors foreclosing on the Urbans’ properties, did not respond to a request for comment.