Biggest Chicago Real Estate Foreclosures of 2025

Lenders across the Chicago metro went to court this year to settle troubled loans, bringing major foreclosure lawsuits downtown, in the suburbs and on the South Side.

The distress spread into hospitality, retail and even niche assets such as downtown parking garages, but the city’s office buildings were the major target. Chicago’s office market has struggled to recover from the pandemic-era drop-off, with vacancy rates still twice as high as their pre-pandemic level. In October, the central business district’s vacancy rate hit 28 percent, according to CBRE.

The Real Deal tallied the largest foreclosure lawsuits we saw in 2025. Properties are listed along with the amount lenders are looking to recover.

The list includes only cases where lenders filed foreclosure lawsuits. In some cases, landlords were able to stay out of court by handing over the keys to buildings through deeds-in-lieu of foreclosure. In other instances, lenders and special servicers refused compromise and went to court.

Illinois Center | $260 million

AmTrust’s Jonathan Bennett, LNR Partners’ Arne Shulkin; 111 E Wacker and 233 N Michigan (Linkedin, Loopnet, Getty, starwoodpropertytrust)

In a dispute that spilled into court in 2024 but continued through 2025, AmTrust Realty’s grip on the massive Illinois Center complex slipped after months of trying to stave off distress.

In November 2024, special servicer LNR Partners filed to foreclose on the New York-based landlord’s $260 million loan for the two-tower property at 111 East Wacker Drive and 233 North Michigan Avenue. The trouble started when the U.S. Department of Health & Human Services vacated 170,000 square feet in 2023, leaving a hole in the 2.1 million-square-foot complex.

AmTrust CEO Jonathan Bennett had previously claimed the firm was working toward a resolution, but LNR alleged the landlord stopped paying full debt service in January. Complicating matters, LNR claimed AmTrust never properly updated the loan’s guarantor after the 2016 death of co-founder Michael Karfunkel—a technical default that could pile on massive interest penalties.

1100 South Michigan & 1101 South Wabash | $187 million

Chicago hotelier Sue-Mei Yen, Cassie Yen, ACORE Capital CEO Warren de Haan and with 1100-1101 S. Michigan Avenue (Getty, ACORE Capital, Google Maps, Facebook/Kendall College Capstone)

Su-Mei Yen, a longtime fixture in Chicago’s hospitality scene, faced a double-barreled legal crisis this summer.

San Francisco-based lender ACORE Capital hit Yen and her firm, SB Yen, with a $187 million foreclosure suit targeting two major South Loop hotels: the 172-room Best Western Grant Park and the 30-story Homewood Suites by Hilton. ACORE alleged that Yen’s firm not only defaulted on the loan but also failed to deposit hotel revenues into the required accounts, diverting cash to pay back affiliates instead.

The foreclosure came as Yen battled a separate lawsuit from Chinese EB-5 investors who claim they were defrauded out of over $18 million meant for the projects. The investors allege Yen and her daughter, Cassie Yen, mismanaged funds and intentionally allowed the loans to default, jeopardizing their green card prospects.

ACORE has been coming after debtors elsewhere in Chicago this year. The lender seized a 16-story River North building from landlord JRE Partners in September through a deed-in-lieu. Property records show JRE borrowed $73 million from ACORE to finance the purchase, and the deed in lieu valued the property at nearly $60 million.

Westbrook Corporate Center | $87 million

In the suburbs, CWCapital Asset Management rejected a lowball buyout offer from Group RMC and instead filed an $87 million foreclosure suit against the New York-based landlord.

Group RMC had offered to buy out the note on the five-building Westbrook Corporate Center in Westchester for $52.5 million—roughly half the loan’s original balance—after a major tenant, Follett Higher Education Group, slashed its footprint.

Despite the landlord’s offer to inject $6 million in fresh equity to stabilize the 1.1 million-square-foot campus, CWCapital rejected the proposal and moved to seize the property. It’s a harsh blow for Group RMC, which had spent the last few years aggressively acquiring suburban office campuses across the Midwest, betting on a recovery that has yet to materialize.

Ruben Espinoza’s Southwest Side Portfolio | $68 million

Ruben Espinoza Faces More Lawsuits from Lenders, State Senator — K-Star Asset Management’s Lindsey Wright, Rialto’s Jeff Krassnoff and Senator Robert Martwick Jr. (K-Star Asset Management, Rialto, State Senator Robert Martwick, Getty)

Florida-based investor Ruben Espinoza spent 2025 mired in legal fights, capped by a $68 million foreclosure filed by Wilmington National Trust on two Southwest Side commercial properties.

The unpaid debt is split between two properties: Espinoza allegedly owes $43 million, including interest and fees, on the 661,000-square-foot Chicago Business Center at 2600 West 35th Street, according to Wilmington. He owes another $24 million at a 110,000-square-foot distribution center on South Damen Avenue.

A receiver has already been appointed to take control of the assets, but that was just the start of Espinoza’s legal troubles this year.

Espinoza is facing a lawsuit from a commercial tenant at the South Damen Avenue building Wilmington is foreclosing on. Produce wholesaler Galfresh Produce alleges Espinoza took a deposit and first month’s rent but never allowed them to move into the building.

Espinoza sued business partner Igor Gabal over a $6.2 million insurance payout at a West Adams Street building. Both investors are claiming the other misappropriated funds and trying to shut each other out of shared bank accounts. In October, a judge ordered Espinoza to pay $631,000 in a separate case where state Sen. Robert F. Martwick Jr. accused Espinoza of not paying Martwick’s law firm.

Elsewhere, Espinoza is batting a lender who is moving to foreclose on a $9.6 million loan tied to a River North loft portfolio. Rialto Capital filed a foreclosure in March, but Espinoza is disputing the foreclosure.

The Poetry Garage | $33 million

Richard Kaplan and John Hammerschlag with the Poetry Garage at 201 West Madison — Richard Kaplan and
John Hammerschlag with the Poetry Garage at 201 West Madison (Getty, Syndicated Equities, Hammerschlag & Co., Inc., Google Maps)

In a dispute over a downtown parking garage, lender Swiss Re wasn’t satisfied with taking back the troubled building. It came after the investors too.

Lender Swiss Re moved to foreclose over a $33 million loan on the literary-themed Poetry Garage at 201 West Madison Street. The investor group led by Richard Kaplan of Syndicated Equities and John Hammerschlag of Hammerschlag & Co. defaulted on the loan in March, reinsurance giant Swiss Re said in court.

Swiss Re gained control of the property with a $21.5 million credit bid this fall, and later secured a $9.6 million deficiency judgment against the owner group to cover the rest of the loan balance.

The investors had struggled with the parking structure since the pandemic decimated Loop office occupancy, securing multiple loan modifications before finally defaulting on the $33.2 million debt when it matured this spring.