Shai Wolkowicki Faces More Chicago Real Estate Lawsuits

Longtime Chicago real estate investor Shai Wolkowicki is facing two new battlefronts in his sprawling legal war against various ex-partners and lenders, after two new lawsuits were filed over the course of the last week in Cook County court.

South Side multifamily investor Andrew Oshay filed a lawsuit against an entity managed by Wolkowicki and his investment partners, which include Chikoo Patel and Animesh Ravani, who are each involved in back-and-forth finger pointing over the collapse of a portfolio of dozens of Chicago apartment buildings.

Plus, Wolkowicki was already locked in bitter legal fights with his former retail development partner in GW Properties, Mitch Goltz. Now, the ex-duo is now facing an Old National Bank foreclosure lawsuit filed last week for vacant land parcels they’ve been trying to sell in Orland Park and Joliet. That’s where they were once set to build medical office space for Duly Health Care before the would-be tenant backed out, causing a rift between the developers and CBRE brokers, ultimately leading to a lawsuit over a $6 million commission request that got privately settled.

Oshay’s lawsuit against Wolkowicki’s venture reveals more about how a collection of properties in the Jackson Park area near the newly opened Obama Presidential Center got thrust into financial distress, as well as a web of litigation spun by multiple investors. Meanwhile, the $5.8 million foreclosure suit brought by Chicago-based Old National adds another seven-figure debt the bank is trying to collect from a Wolkowicki real estate venture, on top of $16 million it loaned to him and Patel for a Springfield apartment complex that fell into financial trouble.

The new pair of lawsuits paints a clearer picture of the severe financial distress across multiple arms of Wolkowicki’s ventures, adding a fresh chapter of chaos to his ongoing feuds with Patel and, separately, Goltz.

Wolkowicki said the property Old National is targeting for foreclosure at 7420 West 159th Street in Orland Park is being marketed for sale, and his partnership is in the midst of finalizing a recapitalization plan to resolve that lawsuit.

Regarding the South Side multifamily lawsuit brought by Oshay, Wolkowicki said, “I was a passive investor with no operational involvement or oversight responsibilities until the previous manager was removed. There are numerous lawsuits which we filed that remain pending related to these properties. I cannot comment on active litigation. We intend to vigorously defend any lawsuits against me.”

Patel’s attorney declined to comment, as did Oshay’s attorney. Goltz also declined to comment beyond stating he intends to resolve the Old National dispute.

The South Side Siphon

The drama at the South Side apartment portfolio — which includes buildings at 6750 South Merrill Avenue, 6820 South Oglesby Avenue and 6952 South Paxton Avenue — stems from what was originally supposed to be a rescue mission.

According to the complaint, Oshay’s venture GRV Jackson Park Investors LLC, represented by attorney Andrew Porter, brought Wolkowicki and Patel in to save the portfolio from the alleged mismanagement of former property overseer Tyler DeRoo, a figure tied to the notorious EquityBuild scheme. Oshay agreed to dilute his group’s equity down to 50 percent, with the expectation that Wolkowicki, along with partner Animesh Ravani, would inject fresh capital to stabilize the distressed assets.

Instead of using their own cash, however, Wolkowicki’s camp turned to Milwaukee-based F Street, securing a $2.5 million unsecured loan from the firm that was subordinate to $6.3 million of senior debt held by Merchants Bank of Indiana.

Oshay’s lawsuit claims that rather than investing that $2.5 million into the deteriorating properties, Wolkowicki and his partners immediately diverted more than 50 percent of the funds to other LLCs they controlled “for purposes that had no benefit” to the landlord company. The alleged transfers included:

$500,000 to GRV 352-62 E 60th Street LLC;
$350,000 to DL 6811 S Clyde LLC;
$250,000 to DL 6811 S Paxton LLC;
$149,933 to GM Jags LLC;
$95,333 to AKR Law Group, Ltd. (an affiliate of Ravani); and
Tens of thousands more to entities managed by Wolkowicki, including STRG Acquisitions and Salina Investment Partners LLC.

Unsurprisingly, without the needed capital, the buildings fell into decrepit disrepair. The city of Chicago sued the ownership group in April 2025 over code violations at the Paxton property, citing cracked parapet walls, broken stairs and the accumulation of trash. That resulted in a court order to completely vacate the premises. The city filed a similar suit against the Oglesby property in July 2025.

By February this year, Merchants Bank had had enough. The senior lender declared a default, citing multiple boiler failures at buildings within the portfolio that caused ceiling collapses, unpaid real estate taxes and a failure by the borrowers to disclose financial records. Oshay is now demanding the court force Wolkowicki to turn over the accounting books.

While Wolkowicki has sought to blame Patel for the downfall, accusing him of embezzling $10 million away from the properties in a “Ponzi-like scheme” that left investors with empty pockets and properties in blight, Patel has countersued Wolkowicki for allegedly getting misled into signing an “unconscionable” settlement agreement.

Suburban Woes

If the South Side apartment debacle and the Patel countersuit weren’t enough, Wolkowicki is also facing the loss of two suburban land parcels.

On May 20, Old National Bank filed a foreclosure complaint against Chicago-based GW Property Group, LLC-Series 11, naming Wolkowicki and Goltz as personally liable guarantors.

The bank alleges the developers defaulted on two loans when they failed to pay off the balances at their maturity date of February 5 of this year. The properties on the chopping block are:

7420 West 159th Street in Orland Park: The bank is seeking $3,298,906.51 in unpaid principal; and
2000 West Jefferson Street in Joliet: The bank is seeking $2,520,076.24 in unpaid principal.

Both properties were cross-collateralized and cross-defaulted. Old National Bank is asking the court to foreclose on the mortgages, appoint a receiver and hit Wolkowicki and Goltz with personal deficiency judgments.While Wolkowicki is sorting out his legal issues, including a separate lawsuit he brought against Goltz over the handling of proceeds from a $31 million Evanston property sale last year, Goltz has continued to focus on retail development through his new firm GTZ. Goltz has a deal in place that would bring a huge Amazon store to an Oak Brook corporate campus, and would require the demolition of an office park and construction of a Costco-like warehouse for the e-commerce giant’s entry into big-box retail.