After a day of campaign rallies and meetings, JFK attended a DNC/DSC event hosted by Grant at the Waldorf Astoria hotel in New York City. The event was held on October 12th, 1960, less than a month before the Presidential general election. 

The DNC Inaugural Gala was a pre-inaugural ball organized by Frank Sinatra and Peter Lawford at the D.C. Armory on the eve of Inauguration day, January 19, 1961, and is considered as one of the biggest parties ever held in Washington, D.C. Sinatra recruited many Hollywood stars who performed and attended, and went as far as convincing Broadway theatres to suspend their shows for the night to accommodate some of their actors attending the gala. With tickets ranging from $100 per person to $10,000 per group, with funds benefitting the Democratic National Committee. Performances and speeches included Fredric March, Sidney Poitier, Nat King Cole, Ella Fitzgerald, Gene Kelly, Tony Curtis, Janet Leigh, Bill Dana, Milton Berle, Jimmy Durante, Harry Belafonte, and Sinatra himself.

The Inaugural Concert was held at Constitution Hall earlier that evening. The National Symphony Orchestra performed. 

In this picture, Ambassador Stockdale greets Irish troops. 

Evelyn Lincoln served as the personal secretary to John F. Kennedy from his election to the United States Senate in 1953 until his death in 1963. These letters span Kennedy's presidency, from 1961 to 1963, and include mention of the Cuban missile crisis, JFK's visits to Ireland, and his ancestral Irish past. Also of note is the "Project Mercury" stamp used on the Dec. 1962 letter. Project Mercury was the first human spaceflight program of the United States, running from 1958 through 1963. 

After Speaker Sam Rayburn's death in November 1961, McCormack acted as Speaker until winning election to the post in early 1962; he served from January 1962 until retiring from the House in 1971. These cordial letters mention a 5000 ton allotment of sugar from the US to Ireland as well as their mutual friend, Florida Senator George Smathers.  

Upon invitation from Grant, President Kennedy attended the 1963 Orange Bowl in Miami, Florida. Pictured in the the left of the photograph is an Alabama cheerleader who was overcome with emotion after meeting the President. President Kennedy is seen laughing after the encounter. 

Only a day after President Kennedy was assassinated in Dallas, Grant received this telegram from JFK's brother Robert, inviting him to the wake for President Kennedy. 

Pictured here (from left to right) is Bob Hope, Ambassador Stockdale, and Bing Crosby together. The three were on the set of the movie,  On The Road to Hong Kong. 

The 1960 Democratic National Convention was held in Los Angeles, California, on July 11–July 15, 1960. It nominated Senator John F. Kennedy of Massachusetts for President and Senator Lyndon B. Johnson of Texas for Vice President. Kennedy's brother, Robert, was his campaign manager. Grant was a delegate from Florida.

These letters from President Kennedy to Ambassador Stockdale in Ireland span from 1961 to 1962.

This letter was sent from First Lady Jackie Kennedy to Grant in August of 1960. In the letter, Jackie thanks Grant for the gifts he had sent them, namely a thin Omega wristwatch. President Kennedy would go on to wear this watch during his inaugural address. 

These letters from then Senator Jack Kennedy to Grant range from 1957 to 1959. 

This invitation was sent to Mr. and Mrs. Grant Stockdale in August of 1953. The wedding included more than 800 guests and was held in Newport, Rhode Island. 

On Memorial Day in 1963, Grant joined President Kennedy at a ceremony held at the Tomb of the Unknown soldier in Arlington National Cemetary. 

After attending a ceremony with President Kennedy on Memorial Day in 1963, Grant is seen here with President Kennedy and his son, John Jr. in the President's Outer Office in the White House. 

This correspondence with Indian Ambassador to Ireland, Vijaya Pandit, took place in July of 1961 while Grant was serving as US Ambassador to Ireland. 

This poem was written by Grant's wife, Alice Boyd Stockdale, and was sent to President Kennedy. 

These letters between Ambassador Stockdale and Senate Majority Leader Mike Mansfield spanned the year of 1961.

This letter was sent from Robert F. Kennedy to Grant in June of 1960.

In this letter, President Kennedy praises Grant after his resignation from his ambassadorship. 

These letters were exchanged between Grant and Senator Ted Kennedy from 1961 to 1963. 

These letters, sent by Senator Ted Kennedy to Grant's wife, Alice Boyd, span three years, from 1964 to 1967. 

This telegram was sent from President Kennedy to Ambassador Stockdale in regards to the President of Ireland's visit to the US Embassy. 

This letter was written by Grant in 1959 to "Jack," or Senator John F. Kennedy. 

This letter was written by President Kennedy to Ambassador Stockdale in May of 1961. The letter provides background and context for Stockdale's role as Ambassador, as well as commenting on the state of relations in Ireland. 

Grant sent this to Evelyn Lincoln, President Kennedy's personal secretary. It includes the bills he passed while serving in the Florida House of Representatives.