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From distressed debt to apartments: Envoi locks in $64M Fortress loan for LaSalle office to resi conversion

Former YMCA HQ to be transformed into 207 apartments with ground retail in partnership with Fortress to fast-track residential overhaul

Cory Faulkner and Nate Ernst of Envoi with 19 South LaSalle Street

The team behind the residential conversion at the site of a former YMCA headquarters in downtown Chicago has assembled a $64 million financing stack, greenlighting the construction work ahead of its 2027 timeline.

Chicago-based Envoi Partners snagged a construction loan from Fortress Investment Group in the residential adaptive reuse project of the 16-story Loop building at 19 South LaSalle Street. The financing mix will include senior debt, federal historic tax credits and private capital, Envoi Partners confirmed via email. Further details of the financing breakdown were not immediately available. 

The developers secured financing and building permits and are expected to convert 207,000 square feet of office space into 207 apartments and 6,811 square feet of ground-floor retail in 15 months, according to a statement from the company. The team told The Real Deal  that demolition is nearly complete and structural demolition and interior construction will begin immediately. The retail level will front both LaSalle Street and historic Arcade Alley, the statement added.

A person familiar with the deal told TRD that the developers received a fee waiver for their permit towards the project. 

“Reaching this point — permit in hand, loan closed and construction starting — is the culmination of nearly two years of disciplined work,” said Nate Ernst, founding principal at Envoi.

Envoi, led by Ernst and Cory Faulkner, acquired the building’s loan note for $4.2 million in October 2024 in partnership with Chicago-based investor Igor Gabal. Gabal has since exited the association and Envoi assumed ownership ahead of the apartment rebuild.

Hartshorne Plunkard is the architecture firm, and Power Construction is the general contractor on the project. 

The 132-year-old building was granted a landmark status in December, which will protect the exterior facade designed by William Le Baron Jenney — famed American architect and engineer credited with shaping the city’s skyline. For three decades between the 1920s and 1950s, the building was the headquarters of YMCA’s educational programming. 

Completed in 1893 by Jenney & Mundie and expanded in 1913 by successor firm Jenney, Mundie & Jensen, the Loop structure is an early example of a steel-frame skyscraper built in the aftermath of the Great Chicago Fire in 1871. 

Its design blends late 19th century historicism with the emerging Chicago School emphasis on structural expression and restrained ornamentation.

The building is one of only two remaining Jenney-designed structures in the Loop, alongside the New York Life Building across LaSalle Street. Though altered over time, including changes to storefronts and the removal of its cornice, the property retains much of its original massing, materials and window patterns.

The adaptive reuse project is part of both public and private efforts to revitalize the LaSalle Street corridor. Major projects to that end include Google’s new Midwest headquarters along LaSalle at 100 West Randolph Street in the Thompson Center, where construction is expected to wrap up by 2027.

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