Designed by architecture firm Tracy and Swartwout in the Beaux-Arts style, the building opened in 1901 as the Yale Club of New York City's clubhouse.

The building contained offices for the United States Maritime Service during World War II, and it housed the Organized Reserve after 1948.

[12] Prior to the development of 30 West 44th Street, the neighborhood contained a slaughterhouse, stables for stagecoach horses, and a train yard for the elevated Sixth Avenue Line.

[24] The lowest portion of the facade contains a water table of granite, above which the first two stories are clad with rusticated limestone blocks.

On the third story, the two center bays contain decorative panels on either side, and there is a balcony with ornate brackets directly above these windows.

[28] The colonial-style grill room measured 40 by 47 ft (12 by 14 m) and contained wooden walls, white floor tiles,[28] and a large fireplace donated by the class of 1867.

This space contains oak floors, gilded fixtures, lighting sconces, and chandeliers similar to those in the original Yale Club.

[31] The Grill Room is accessed by a spiral marble staircase beneath the foyer; it contains a mahogany bar, a recreation of the Old King Cole mural, and other furnishings.

[24][5] To accommodate the growing membership, the Yale Club unsuccessfully attempted to acquire an existing building in midtown Manhattan, ultimately deciding to develop a new structure.

[5][6] The Yale Club had hired Evarts Tracy and Egerton Swartwout to design an 11-story clubhouse on the 50 by 100 ft (15 by 30 m) site.

[25][24] The building's facade was to be made of red brick and white stone, while the interior would contain various club rooms, restrooms, and bedrooms.

[42] The Yale Building Company was formed to oversee the clubhouse's development, obtaining a mortgage loan to fund the project.

[24][39] The option on the land was initially supposed to expire at the end of February 1900, but this deadline was later extended by a month to allow the club to raise money for the acquisition.

[24] The architects filed plans with the New York City Department of Buildings in July 1900,[45][46] at which point the Yale Club began soliciting bids from general contractors.

[53][56] Yale alumnus James Gamble Rogers designed a 22-story clubhouse on the site at 50 Vanderbilt Avenue, and construction began in 1913.

[57][58] The Vanderbilt Avenue clubhouse opened in June 1915, and the Yale Club vacated its old headquarters at 30 West 44th Street.

[57][59] The clubhouse's main entrance was slightly truncated, and a recessed areaway in front of the building was removed,[17] when the New York City government widened 44th Street in 1916.

[61] A holding company, operated by Delta Kappa Epsilon (DKE) fraternity, bought 30 West 44th Street in July 1916.

The ground-floor and basement entrances were modified, and Oswald C. Hering and Douglas Fitch designed a penthouse with locker rooms and squash courts.

[64] The clubhouse hosted events such as fundraisers,[67] the fraternity's 75th-anniversary celebration,[68] and a dinner for former Cuban president Mario García Menocal.

[70][71] The Army and Navy Club had been forced to relocate from its previous clubhouse at 112 West 59th Street, which had been sold to a developer that February.

[80][81] Following a $136,000 deficiency judgment against the Army and Navy Club, United States Trust deeded the property to the Thirty West Forty-fourth Street Corporation in December 1933.

[64] A client of William H. Whiting acquired the building in August 1939, with plans to spend $250,000 converting the structure into apartments.

[64][88] The New York Herald Tribune reported in September 1942 that the building had been sold, although the United States Trust Company denied the news.

[96] The government of the United States announced in December 1947 that it would convert 30 West 44th Street to offices for the Organized Reserve, which was to relocate from various locations in Manhattan.

[96][99] The General Services Administration (GSA) managed 30 West 44th Street along with other federally owned buildings in New York City.

[104] The training center at 44th Street quickly became one of the largest such schools operated by the United States Army,[105] with 700 students in 1953.

[96] The 301st Logistical Command trained at 30 West 44th Street,[102] and the 306th Special Services Company, an entertainment unit of the U.S. Army, also used the building as its headquarters.

Columbia University and City College of New York both expressed interest in acquiring 30 West 44th Street and using it as an office.

[124] Penn's alumni magazine The Pennsylvania Gazette wrote that the clubhouse hosted events such as "monthly wine tastings, business gatherings, happy hours, and speaker series", as well as parties.