Roswell Leavitt Gilpatric (November 4, 1906 – March 15, 1996) was a New York City corporate attorney and government official who served as Deputy Secretary of Defense from 1961–64, when he played a pivotal role in the high-stake strategies of the Cuban Missile Crisis, advising President John F. Kennedy as well as Robert McNamara and McGeorge Bundy on dealing with the Soviet nuclear missile threat.

His duties as a scholarship boy, which included waiting on tables and cleaning rooms, kept down his participation in extracurricular activities at Hotchkiss, but he was a member of the Cum Laude Society.

Following his graduation, Gilpatric went to work for the New York City law firm of Cravath, Swaine & Moore, where he became a partner and where he practiced when not serving in government.

At one point during the tense standoff of the Cuban Missile Crisis, McGeorge Bundy was arguing for United States bombing of Cuba to eliminate the threat of a Soviet nuclear attack.

It was Gilpatric's intervention that changed the direction of the discussion, according to Harvard professor and former Department of Defense official Graham T. Allison, who authored a book, Essence of Decision, about the crisis.

Proposing the blockade was McNamara and Gilpatric's solution to providing President Kennedy with a strong response – but short of the airstrike that McGeorge Bundy and others were pushing.

In the Eisenhower administration, Gilpatric headed a secret task force charged with "preventing Communist domination of Vietnam."

[13] Gilpatric was also a member of a special task force which hatched "Operation Mongoose", a dirty tricks campaign aimed at destabilizing the government of Fidel Castro in Cuba.

And the President never saw him unless at some ceremonial affair, or where he felt he had to make a record of having listened to LeMay, as he did on the whole question of an air strike against Cuba.

When McNamara met the Brooklyn-born lawyer at Kennedy's suggestion, according to historian Arthur Schlesinger Jr., he found Gilpatric "easy, resourceful and intelligent, and the partnership was immediately sealed."

Gilpatric made himself an "indispensable" figure in the Kennedy administration, wrote longtime JFK aide Ted Sorensen.

[17] Gilpatric sometimes attracted the attention of the press in his personal life, and he was often linked romantically to former First Lady Jackie Kennedy.

[18] A fellow Wall Street attorney offered for sale in the 1970s a trove of personal letters between Gilpatric and the former First Lady.

The controversial airing of his private correspondence with the former First Lady so annoyed Gilpatric that he formally requested that four letters written to him by Jackie Kennedy be withdrawn for sale by the auction house as they had been stolen from his New York City law office at Cravath.

[19] Another strange twist involved Gilpatric after his death, when a 2008 book by former acting director of the FBI L. Patrick Gray alleged that Gilpatric, back in private practice and with Time magazine as a client at the time of the Watergate break-in, learned from sources at the magazine that a senior official at the FBI was leaking to Sandy Smith, one of its reporters.

During the discussion, Nixon suggested that they bring in Felt's accuser: President: Well, why don't you get in the fellow that's made the charge, then.

[26] Gilpatric died of prostate cancer on March 15, 1996, in New York City, and was buried in Somesville, Mount Desert Island, Maine, where he had a summer home.