Glenstar, Halloran Purchase of Loop Office Tower at Discount

The pairing of Chicago-based Glenstar and Minnesotan investor Patrick Halloran are acquiring another building together at a steep discount, this time it’s 500 West Monroe Street in Downtown Chicago.

While the sale price of the building was not disclosed, Crain’s reported that the distressed $270 million loan on the building was acquired for less than $100 million. San Francisco-based Spear Street Capital, who surrendered the building through deed-in-lieu of foreclosure, bought 500 West Monroe for $412 million in October 2019.

Glenstar and Halloran claim that they’ll be injecting cash to revamp portions of the building with a focus on new amenities, according to the outlet. The venture hopes that a fresh coat of paint will reignite leasing momentum on the property. Last year, when the loan on the tower hit the market, the building was around three-fourths leased. In 2027, GE HealthCare’s lease will expire, and 572,000 square feet will come available.

Spear Street appears to have pivoted after defaulting on the West Monroe property in 2025. In early May, they entered into a contract to buy the 146,000-square-foot property at 1201 West Lake Street in Fulton Market for around $40 million. To complete the Loop exit, they’re in the process of unloading 225 West Wacker Drive for another deep discount.

Across the aisle, Glenstar and Halloran are doubling down. The duo are investing $30 million in a massive renovation of 200 South Wacker Drive, hoping to score tenants with an “amenity blitz.”

While there’s evidence of downtown office momentum, either through redevelopment or bets by high-profile tenants, the market has still seen weakened demand overall, according to the publication. Elevated interest rates and new, hybrid work schedules are still tearing into the value of office space outside of trophy office scenarios, causing developers to look into mixed-use redevelopments.

— Hunter Cooke