The brick building at 161 Duane Street was originally constructed in 1843 as a private house. From 1860 until 1920 the structure housed a whalebone cutting business (as can be inferred by the painted sign on the facade). The workers here created hoops for horse whips, women's skirts, corset stays, collar stiffeners, and umbrella ribs out of whalebone, but by the early 20th century, fashion, material technology, and a significant decline in American whaling rendered this business largely obsolete. In the 1890s the whalebone work moved to the top floors, while the Ye Olde Tavern (seen here in 1902) moved into the ground floor. When the firm's final owner, a man named George Massmann, retired in 1920, he had worked in this building since 1866 (under both of the previous owners).

Later in the 20th century, the building was home to a shoe company and likely dozens of other unknown businesses. During that time the facade and its Whalebone sign were painted white, and the older faded sign attached above the second floor was removed.

In 2002 architect and developer Joseph Pell Lombardi purchased this building and its neighbor at the corner (at left). Known as the Mohawk Building—it was once the home to the Mohawk Electric Company— the 1891 corner structure was built for a confectioner. Pell combined the two interiors for residential condos while restoring both facades and repainting the building's eponymous signage.