The heart of the clubhouse is the main lounge, a large room with a high, ornate ceiling and large columns and walls lined with fireplaces and portraits of the five Yale-educated United States presidents, all of whom are or were members of the Yale Club: William Howard Taft, Gerald R. Ford, George H. W. Bush, Bill Clinton, and George W.

One of the incorporators was Senator Chauncey Depew, whose 1890 portrait by the Swiss-born American artist Adolfo Müller-Ury hangs in the building.

Designed by architect and Yale alumnus James Gamble Rogers in conjunction with the construction of Grand Central Terminal,[2] it was largely paid for by money raised or contributed by President George C. Ide of Brooklyn (whose portrait by George Burroughs Torrey hangs in the building).

Its location was chosen because it was believed to be where Yale alumnus Nathan Hale was hanged by the British Army for espionage during the American Revolution,[12] although the site of Hale's execution has more recently been disputed.

[13] Today, the dress code remains business casual, except in the athletic facilities.

In the fall of 2012, the club began to allow denim to be worn in the library, the Grill Room, and on the rooftop terrace during the summer, but nowhere else, as long as it is "neat, clean, and in good repair.

Before the two Heisman Trophy ceremonies, the un-awarded trophy itself was displayed in the Yale Club's lobby, flanked by portraits of Yale's two Heisman winners, end Larry Kelley (1936) and halfback Clint Frank (1937).

[17] Bork claimed that his injuries required surgery, immobilized him for months, forced him to use a cane, and left him with a limp.

[19] To be eligible for membership, a candidate must be an alumnus/alumna, faculty member, full-time graduate student of Yale University, or a child of one.

According to a book published for the club's 1997 centennial, members at that time included George H. W. Bush, Hillary Clinton, Bill Clinton, Gerald Ford, John Kerry and George Pataki.

In 1972, Frank Mankiewicz famously described John Lindsay as "the only populist in history who plays squash at the Yale Club.