Collection of teenage letters

(Image: RR Auction)

This remarkable collection of personal letters was written by an adolescent Robert Kennedy to his close friend Peter MacLellan, from 1941 until 1945. They provide a fascinating insight into the Kennedy family, Robert's feeling towards his brothers and sister, and their exploits during WWI. Highlights include, in part:

September 26, 1942. "I'm going home this weekend to see my brother Jack who is now going into P. T. boats so I'm getting out to see him because he might be killed any minute."

March 13, 1943. "Jack, the brother whom Jerry McGuire thought had such an easy job behind a desk is now out in the Solomons in a P. T. boat so I'd be very grateful if you'd inform Mr. McGuire of that fact if you see him again. My other brother is still flying and Kick, sister, is going to Africa or England the beginning of April and I spot planes so we all feel quite patriotic."

July 3, 1944. "I am now just sitting around on my big family which is really just what I like. I am now chasing women madly but it looks as if I lack the Kennedy charm as I have yet to find a girl who likes me but then I don't quit easily. Jack just got his back operated on (Did you see the story about his boat in last week's New Yorker) and Joe is flying still in England but is due home home as he has been over there a month more than was necessary now anyway but you know us Kennedys, rough, tough, and always volunteering for the hard jobs."

The collection, comprised of 18 signed letters totalling 49 pages, were sold at an RR Auction sale in 2014 for $31,250.

1956 Adlai Stevenson campaign notes

(Image: Heritage Auctions)

In 1956, Robert Kennedy spent several weeks working as an aide to Adlai Stevenson, following his nomination for president at the Democratic National Convention. RFK had already successfully managed his older brother's 1952 U.S. Senate campaign in Massachusetts, and was looking for experience within a national campaign.

He spent six weeks attending speeches and events, and recorded many of his observations and political conversations during the period in the form of extensive handwritten notes. Amongst these are moments of humour, including a recollection of accidentally eating Stevenson's breakfast:

"Sunday morning after 8:15 Mass went by to see Bill Blair. Asked me for breakfast and as I was hungry ate the Governor's [Stevenson's]. Upon finishing the melon he came in + asked for his. I told him Bill Blair had eaten it + skurried off."

RFK learned a great deal during his six weeks on the Stevenson campaign, although his lack of enthusiasm for the candidate himself led him to vote for the incumbent Dwight D. Eisenhower. However, the experience served him well, and four years later in 1960 he ran the campaign which successfully put his brother in the White House.

This collection of Kennedy's hand-written notes circa 1956, documenting his time with the Stevenson campaign, sold at Heritage Auctions in 2013 for $1,875.

Inscribed James Bond novel

(Image: Bonhams)

In March 1960 author Ian Fleming found himself invited to dinner with the Kennedys, as the guest of his friend Mrs Marion Leiter. The Senator was a huge fan of James Bond novels, and after dinner Fleming entertained the party with his ideas of how to get prevent the Cuban revolution (including convincing locals that Russian radioactivity had poisoned their beards).

From then on he maintained a link to the Kennedy family, regularly sending signed copies of his books to JFK, his brother Robert, and their sister Mrs Eunice Shiver. This copy of Fleming's tenth Bond book The Spy Who Loved Me was inscribed by the author to Robert Kennedy, and sent to him following its publication in 1962. It later ended up in the collection of Paul 'Red' Fay, a close family friend of the Kennedy's and advisor to JFK, and sold at Bonhams in 2010 for $46,360.

Marijuana jail sentence reduction document

(Image: Heritage Auctions)

Dated July 16, 1963, this document bears the signatures of both President John F. Kennedy and his brother, Attorney General Robert F. Kennedy.

The document commutes the sentence of Peter Young, convicted of the illegal importation of marijuana and given a sentence of 50 years in May 1957. Having taken his case to the Circuit Court of Appeals in 1961, Young was later given a reprieve on his sentence by the President himself:

"Now, therefore, be it known, that I, John F. Kennedy, President of the United States of America, in consideration of the premises, divers other good and sufficient reasons me thereunto moving, do hereby commute the sentence of the aforesaid Peter Young to a term of ten years' imprisonment."

The document is one of the few to bear the signatures of both JFK and RFK, and sold at Heritage Auctions in 2006 for $10,755.

1964 Democratic primary press release

(Image: Christie's)

Following his brother's death in November 1963, many Democrats saw Robert Kennedy as his natural successor and clamoured for him to run in the 1964 election. With Lyndon Johnson now in the White House, people saw him as the perfect Vice President.

However, the simple fact was that LBJ and RFK hated the sight of each other and had no desire to run on the same ticket. Johnson said he would rather quit the race than team up with Kennedy, claiming privately "I don't want it that much!", and Kennedy tried to dampen down the campaign to include his name on the ballot during the Democratic primaries.

Prior to the New Hampshire primary, Kennedy released a statement which read, in part: "There have been a number of inquiries about the Attorney general's views on the campaign to write in his name for the Office of Vice President in the primary election in New Hampshire next week. The AG, as he has said, intends to remain with the Justice Dept. thru November and he has not yet decided what he will do after the election."

He then stated he "has not been in touch with anyone in New Hampshire or taken any action to encourage the campaign. In fact he has discouraged in the past and will continue to discourage any efforts on his behalf."

Despite his best efforts, 25,000 people still wrote RFK's name on the ballot. He then decided to run for the vacant New York senate seat, to position himself for a presidential campaign in 1968 following LBJ's victory in 1964. His challenge would force the President to drop out of the race for re-election, but would be tragically cut short when he was shot and killed in June 1968.

This typed copy of Kennedy's press statement regarding the New Hampshire primary ballot, including his own hand-written alterations, sold at Christie's in 2012 for $2,250.