Glenstar Halloran eye $100M-Plus Loop Office Tower Purchase

A duo known for purchasing distressed office properties is circling another Loop office tower.

Chicago-based Glenstar and Minnesota investor Patrick Halloran are under contract to acquire the 46-story, 966,000-square-foot building at 500 West Monroe Street for just over $100 million, according to people familiar with the deal, first reported by CoStar.

The price is expected to be between $100 million and $110 million, a sharp haircut from the $270 million loan tied to the property, according to the outlet. That lower price would put the tower at about $104 per square foot, nearly 63 percent below the loan value, and 76 percent below the $412 million Spear Street paid for the tower in 2019.

The pending sale stems from distress at the top of the capital stack. Current owner Spear Street Capital failed to pay off the loan at maturity in January 2025, triggering a workout process, according to the publication. Lender JPMorgan Chase subsequently tapped JLL to market the debt, with a buyer expected to take control via a deed-in-lieu of foreclosure from the San Francisco-based firm.

The transaction isn’t finalized and could still fall apart as office sales remain difficult to execute. JLL brokers Tom Hall, Bruce Miller, Jaime Fink and Sam DiFrancesca are marketing the building.

If it closes, the deal would extend Glenstar and Halloran’s emerging strategy of scooping up large, well located but underperforming office buildings at steep discounts and plow capital into leasing and upgrades, according to the outlet.

The partners kicked off their run in October 2024 with the $62.1 million purchase of the two-building Presidents Plaza complex near O’Hare International Airport, where they earmarked $16 million for move-in-ready suites. They followed that in January 2025 with a $68 million acquisition of the 40-story tower at 200 South Wacker Drive, alongside plans for a $30 million revamp that includes new amenity space.

The plan for the tower at 500 West Monroe Street is expected to mirror those efforts, according to the outlet. The building was about 75 percent leased when it hit the market, with a weighted average lease term under five years.

— Eric Weilbacher