SUDBURY, MA — Three items signed by John F. Kennedy — two while serving as a senator and one while president — are highly anticipated lots at the Summer Estates and Collections sale scheduled for Sunday, September 8 at Tremont Auctions.

Kennedy released Profiles in Courage in December 1955 while serving as a senator from Massachusetts. First elected to the Senate in 1952, by 1954 Kennedy was in such excruciating pain from injuries sustained during his World War II service in the Navy that he was forced to undergo surgery and take a leave of absence. During this time, he penned a collection of short stories looking at the subject of political courage, an element that would come to define his short presidency. Tremont has an inscribed and signed first edition of Profiles in Courage in the sale with an estimate of $2,500-$3,500. The inscription reads To Walter with very best wishes along with his distinctive signature.

Kennedy would release The Strategy of Peace in 1960 in the run-up to the fall presidential election. The book was a collection of speeches on policy made during the campaign. Tremont’s copy is inscribed To Bob with warm regards and very best wishes. Tremont believes ‘Bob’ to be Bob Gore, the inventor of Gore-Tex and a pioneer in the development of polytetrafluoroethylene (PTFE), used in everything from space suits to computer cables. The book is estimated at $3,000-$5,000.

Kennedy’s famous inaugural speech upon assuming the office of president in January 1961 still resonates to this day. His statement “Ask not what your country can do for you, ask what you can do for your country” came to define the politics of the period, as the Kennedy Administration would launch the Gemini space program and many other forward-thinking initiatives. A press-release version of the speech was signed by Kennedy and sent to its recipient, who framed it and the cover letter from Kennedy secretary Evelyn Lincoln. The three-frame set is estimated at $2,500-$3,500.