The New York Life Building, built over a 10-year period that included the turn of the 20th Century, is one of two remaining office buildings designed by architect William LeBaron Jenny, known as "father of the skyscraper." Built in 1929, the West Town State Bank Building is a mid-rise office building not commonly found in the city's outlying neighborhoods.

The 14-story, 210,000-sf New York Life Building would appear to be a prime redevelopment project, according to its most recent property tax assessment. The Cook County Assessor's office places 89% of the property's value in the 0.4-acre site.

The nine-story, 46,000-sf building at Madison Street and Western Avenue sold for $125,000 in 1995, according to property records, with an adjoining parcel acquired by Wolverine Investments two years later for $145,000. Besides offering banking services to the West Side neighborhood, the property was home to radio stations that targeted the African-American community.