JFK's Irish tweed hat from Éamon de Valera heads to auction

A Donegal tweed hat presented to President John F. Kennedy by Irish President Éamon de Valera is about to go up for auction, more than 60 years after his emotional homecoming visit to Ireland. The fedora, which Kennedy reportedly found too large and rarely wore, is expected to fetch at least $6,000.

The hat is Lot 91 in RR Auction's Fine Autographs and Artifacts Featuring John F. Kennedy sale, which closes on Nov. 11, 2026. According to the auction house's lot listing, de Valera gave it to Kennedy on June 26, 1963, the day the American president arrived in Ireland.

The fedora is made from pure new wool woven in County Donegal and carries three feathers in its outer band. A label inside, signed by weaver P. J. Carr, wishes "joy and health" to whoever wears it. White strips of felt were later added inside the sweatband to help it sit more snugly on Kennedy's head.

President John F. Kennedy's Donegal tweed fedora.

The story of how the hat came to be preserved comes from Martin E. Underwood, a special assistant to Kennedy. In a notarized statement quoted in the RR Auction listing, Underwood wrote that "Kennedy disliked hats but he accepted the gesture." He added that the hat was too big, so JFK aides placed felt inside it. Underwood said Kennedy aide Kenneth O'Donnell gave him the hat after the trip.

A second handwritten note from Underwood, also cited in the listing, is more colorful. He wrote that the Irish president Éamonn de Valera  "insisted he wear it" and that it "came down over his ears." By his account, the hat was a size 7 1/2, while Kennedy wore a 7 or a 7 1/4.

After leaving Underwood's hands, the hat joined the collection of noted JFK memorabilia collector Robert L. White. It was offered as Lot 30 at Guernsey's in March 1998.

The gift reflected a relationship built on shared heritage and mutual respect, even though the two men belonged to very different generations. De Valera, who was born in New York in 1882, was 80 years old and nearly blind when he welcomed Kennedy as the first sitting American president to visit the Republic of Ireland.

Irish president Éamonn de Valera.

Kennedy, the great-grandson of Irish emigrants and the first Irish Catholic president of the United States, was treated in Ireland as a son returning home. The two men shared the spotlight during a four-day trip that included a speech to the Dáil. When Kennedy was assassinated just five months later, de Valera was among the world leaders who traveled to Washington for the funeral.

President John F. Kennedy welcomed on the streets of Dublin in 1963.

The hat is not the only family treasure in the sale. A separate collection comes from the estate of Ann Gargan King, a first cousin of JFK and the daughter of Rose Kennedy's younger sister, Agnes Fitzgerald Gargan. Born in Boston in 1934, she lost both parents in childhood and spent summers with her relatives at the Kennedy compound in Hyannis Port. She later became a trusted presence in the household of Joseph P. Kennedy Sr. and Rose Kennedy, and after Joseph's stroke in December 1961, she helped manage his correspondence, appointments, and daily care until his death in 1969.

Among her items is a color photograph of President Kennedy, Jacqueline Kennedy, and the Johnsons watching the inaugural parade on Jan. 20, 1961. Kennedy inscribed it to his cousin and thanked her for helping to put him in the White House. Jackie added a humorous line of her own, writing that she was "not so sure it was a good idea," according to the press release from RR Auction.

The collection also includes an original life preserver from the Marlin, the 52-foot motor yacht Joseph Kennedy Sr. acquired in 1952. The white ring, marked "Marlin, Hyannisport," is displayed on a glass-topped table. A dedication from Ted, Eunice, Pat, and Jean Kennedy reads, "To Ann and Tom, who shared happy times on the Marlin with all of us," as quoted in the press release.

Also on offer is a handwritten note from Jackie to her father-in-law about Christmas plans in Palm Beach. In it, she tells him, "Don't you dare go to Palm Springs," and says Caroline had him "slightly confused with Santa Claus," according to RR Auction. Other keepsakes include a birthday card Jackie painted for Joseph Kennedy in 1967 and a White House stationery card signed by Caroline and John Jr.

Elsewhere in the sale, collectors can bid on a Top Secret letter JFK signed three days after the failed Bay of Pigs invasion, ordering a review of the operation. Original NBC Radio recordings from the day of his assassination are also being offered.

Full details are available at www.rrauction.com.