J
onathan Holtzman is facing another high-stakes foreclosure lawsuit over a Chicago apartment deal gone wrong. This time, his Michigan-based company City Club Apartments and other investors are at risk of losing a 190-unit property in the Loop to lender Prime Finance, which filed a $69 million foreclosure lawsuit this week. The complaint alleges that the ownership group missed its June loan maturity date on a $66 million loan taken out in 2022 using the property as collateral.

    This case joins another high-profile multifamily foreclosure suit against Holtzman's company, which was resolved earlier this year when lender Ares seized a South Michigan Avenue property worth $80 million. It's also at least the second Chicago multifamily foreclosure suit faced by a Holtzman-led venture in two years. In March, Old National Bank sued Holtzman over a defaulted $25 million debt on a Gold Coast property.

    Holtzman and his firm have not commented on the latest lawsuit, nor has Prime Finance or co-owner Wayne Moretti of Lexington Homes. The city's multifamily market is experiencing distress, with several large apartment deals showing concerning performances in recent months. Holtzman's own Fisher Building City Apartments are struggling to meet debt service obligations, with debt costs outpacing revenues.

    Holtzman has a long history with the 190-unit property at 63 East Lake Street, which was originally built in 1927 and converted into housing in 2006. He had a falling out with a previous partner over the building's value in 2017, when he bought out their interest for nearly $70 million. Given recent interest rate hikes and the ownership's inability to sell or refinance, it's likely that the property has lost significant value since then.