In 1918, the Waterman Pen Company began leasing the property and initially announced plans to renovate the existing building and replace its facade, at an estimated cost of $100,000.^[4][5][6] However, Waterman instead built an entirely new building, at a cost of $225,000.^[3] Designed by Holabird and Roche, it was the first new building to be built in Chicago's Loop following the start of World War I.^[3] The exterior was clad in blue terra cotta and encaustic mosaic panels, while the interior featured black walnut furnishing and fixtures, a vaulted ceiling decorated in silver and gray, and cork tile flooring.^[1][7][8] Waterman moved into the building on May 10, 1920.^[2][9][1][8]

In 1922, the Chicago Business College began leasing the sixth floor of the building.^[10][11] In 1923, the White Star Line began leasing the building's second floor for $10,000 a year.^[12] On October 20, 1938, Three Sisters, a woman's apparel shop, opened its fifth Chicago-area store in the Waterman Building.^[13][14] On February 21, 1952, Mary Jane Shoes opened its store in the building.^[15][16][17]

In the 1960s, the building was home to Stanley Green's, a kosher cafeteria and buffet.^[18] The cafeteria was located on the ground floor, while the lower floor featured the dining room and cocktail lounge.^[18] From 1967 to 2018, the restaurant Beef and Brandy was located on the ground floor, while its bar, the Bar Below, was located on the lower floor.^[19][20] In 2018, the building was sold and Sonder Corp. intended to renovate it and open a 41 room hotel in the top four stories, with retail on the first two floors.^{[21][19][22][23]} However, this plan did not come to fruition, and the building has been again listed for sale.