John F. Kennedy personally owned gray felt Henry the Hatter fedora, custom made in Detroit and retaining its original black grosgrain ribbon. The interior sweatband is gold-stamped “JFK,” identifying the hat as having been specially produced for the President.

John F. Kennedy custom engraved sterling silver cigarette box presented to Benjamin A. Smith II as a wedding gift from President Kennedy and the four fellow ushers in Smith’s wedding to Barbara (“Sis”) Mechem.

Jacqueline Kennedy Onassis heartfelt two-page autograph letter signed (“Jackie”) to Barbara Smith, widow of Benjamin A. Smith II, written from her residence at 1040 Fifth Avenue and dated October 6, 1991

Jacqueline Kennedy and her mother, Janet Lee Auchincloss, autographed First Day Cover honoring President John F. Kennedy and the issuance of the 1964 JFK Memorial postage stamp

John F. Kennedy’s personally owned Duofold Style 622 thermal long johns, a remarkable surviving article of the President’s wardrobe that offers a rare and deeply personal connection to the hidden medical struggles that defined much of his adult life. Manufactured by Duofold Inc. of Mohawk, New York, the garment is constructed in the company’s distinctive two-layer cotton and wool design and exhibits extensive wear consistent with prolonged personal use.

John F. Kennedy’s personally owned white Brioni Roma dress shirt from the wardrobe of the 35th President of the United States, accompanied by exceptional provenance tracing its ownership to Mary B. Gallagher, President Kennedy’s longtime personal secretary and executive assistant.

Cecil W. Stoughton’s Air Force One passenger manifest from the return flight departing Dallas on November 22, 1963, documenting the occupants aboard the presidential aircraft following the assassination of President John F. Kennedy.

Abraham Zapruder autographed First Day Cover honoring John F. Kennedy, issued May 29, 1964, on the official U.S. Postal Service memorial stamp commemorating the late president. The cover features the black-bordered “In Memoriam” cachet with Kennedy’s portrait, dates 1917–1963, and the quote “Ask not what your country can do for you-ask what you can do for your country,” alongside the First Day of Issue cancellation from Boston, Massachusetts.

Jack Ruby autographed original Carousel Club business card, boldly signed in pencil on the verso with the handwritten inscription, “Admit Party Anynite, Jack Ruby.” The card advertises Ruby’s infamous Dallas nightclub, The Carousel, located adjacent to the Adolphus Hotel, and reflects the club’s late-night floor shows and risqué entertainment that placed Ruby at the center of Dallas nightlife in the early 1960s.

Jack Ruby autographed original pencil sketch featuring a meticulously rendered geometric pattern drawn on one side of a folded measuring 8.5 x 11" (sight, folded) and inscribed on one side, “To W.R. Pennington, To the parents of a wonderful boy "Ray" Sept. 1965, Sincerely, Jack Ruby.”

An original 1960 John F. Kennedy presidential campaign pin accompanied by a signed provenance letter detailing its remarkable history. The gold-tone campaign pin, bearing Kennedy’s iconic “K” campaign design, was reportedly personally gifted by Kennedy to a close friend and fellow PT boat captain, Mr. Stower, who later assisted with Kennedy’s 1960 presidential campaign.

White House Press Release, Washington, D.C., November 22, 1963. Original 8.5 x 11” White House Press Secretary release containing President Lyndon B. Johnson’s brief remarks delivered upon arrival at Andrews Air Force Base following the assassination of President John F. Kennedy earlier that day.

Original period White House press release issued on November 22, 1963, announcing the official funeral and public memorial arrangements for President John F. Kennedy following his assassination in Dallas, Texas. Measuring 8.5 x 14”, the release was distributed by the Office of the White House Press Secretary and details the schedule for Kennedy’s repose in the East Room of the White House, his lying in state beneath the Capitol Rotunda, and the funeral Mass to be held at St. Matthew’s Cathedral in Washington, D.C.





Lot #408:George W. Hickey Jr. & Floyd M. Boring – JFK Secret Service Agents – Signed Agents Membership Card

George W. Hickey Jr. Association of Former Agents of the United States Secret Service membership card, measuring approximately 3.5 x 2.25”, issued in 1974 and signed by Hickey as the member in black ink and by Executive Secretary Floyd M. Boring in blue ink

Lot #429: Jack Ruby – Carousel Nightclub – Original Period Business Card – Dallas, Texas

Estimate: $350-$450
Sold: $550 (*Includes Buyers Premium)
Jack Ruby original Carousel Club period business card, advertising the Dallas nightclub located at 131½ Commerce Street, with Ruby identified as host. The card promotes continuous shows featuring burlesque dancers and late-night hours, reflecting the branding and visual style of Ruby’s club during the early 1960s.

Lot #493:Dave Powers & Kenneth P. O’Donnell – Dual Autographed Johnny, We Hardly Knew Ye – Ex. Benjamin Smith

Dave Powers and Kenneth P. O’Donnell dual autographed first edition of Johnny, We Hardly Knew Ye: Memories of John Fitzgerald Kennedy, additionally inscribed to United States Senator Benjamin A. Smith II, one of President Kennedy’s closest lifelong friends and Harvard roommate. Published by Little, Brown and Company, 1972. First edition, first printing.

Lot #534: George Edward Thomas – Valet to President Kennedy – Autographed JFK Memorial First Day Cover

George Edward Thomas autographed John F. Kennedy memorial First Day of Issue cover honoring the 1964 JFK 5¢ memorial stamp release. The cachet features a portrait of President Kennedy above a memorial inscription and his well-known inaugural quotation, “Ask not what your country can do for you — ask what you can do for your country.” Thomas has autographed the cover in blue ink across the lower right portion.

As we prepare future installments of the Collecting Camelot series, we are actively accepting consignments of John F. Kennedy–related artifacts, collectibles, ephemera, and more, and would be happy to discuss any items you may be considering for auction.