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This scrapbook, compiled by Kathleen Kennedy, documents her life during the years 1941 to 1942, when she worked at the Washington Times-Herald newspaper in Washington, D.C. The scrapbook contains pre-printed ruled pages with affixed newspaper clippings, greeting cards, calling cards, invitations, telegrams, and other types of printed ephemera. Clippings of note include Kathleen’s review of the Abbott and Costello film, “Ride ‘Em Cowboy”; an article titled, “English Boys Studying in U.S. Think Our Girls Are Wonderful,” written by Kathleen’s brother, Joseph P. Kennedy, Jr.; and two newspaper columns about her brother, John F. Kennedy, written by journalist and Kennedy family friend, Inga Arvad. Also of note are telegrams sent by Kathleen’s father, Joseph P. Kennedy, Sr.; her future husband, William "Billy" Cavendish, Marquess of Hartington; and Washington Times-Herald editor, Frank Waldrop. The scrapbook also contains telegrams from Kennedy family friends, including Anthony “Tony” St. Clair-Erskine, the 6th Earl of Rosslyn; Abbott Widdicombe; Elsie Talbott Mead; Kirk LeMoyne “Lem” Billings; Robert “Bob” Spalding Coleman; Marian Barkley Truitt and Max O’Rell Truitt; Constance “Connie” Shepard and her fiancé, Henry Gaylord “Gay” Dillingham; Charles Alfred "Chuck" Pillsbury; George Houk Mead, Jr.; Viscountess Nancy Astor; Jane "Pill" Pillsbury; and William Warren "Bill" Scranton. The scrapbook contains 58 telegrams, 33 newspaper and magazine clippings, 17 greeting and calling cards, 13 invitations, and 11 other pieces of printed ephemera.

This photograph album, compiled by Kathleen "Kick" Kennedy, documents her life, travels, and social activities from 1939 to 1942. Photographs document time spent at the Kennedy family’s residences in Palm Beach in Florida, Hyannis Port in Massachusetts, and Bronxville in New York; aboard the S.S. Washington en route to New York City, New York, from Europe; at the 1939 New York World’s Fair; in Sainte-Marguerite-du-lac-Masson in Quebec, Canada; at the Maryland Hunt Cup near Reisterstown, Maryland; at the Berkshire Music Festival (now called the Tanglewood Music Festival) in Lenox, Massachusetts; at Bailey’s Beach in Newport, Rhode Island; as a bridesmaid in the wedding of Kennedy family friend, Anne McDonnell, to Henry Ford II, in Southampton, New York; at the Edgartown Regatta on Martha’s Vineyard, Massachusetts; on a camping trip in Wise River, Montana; on a trip to England; at the Beachcomber Lounge in Boston, Massachusetts; at Club Waikiki in New York City; at the Scranton family estate in Scranton, Pennsylvania; on Lake Minnetonka in Minnesota; at the Coleman and Schweppe family estates in Lake Forest, Illinois; and at parties at both Kathleen’s apartment and the apartment of Kennedy family friend Inga Arvad in Washington, D.C. Other locations pictured include Narragansett, Rhode Island; Greenwich, Connecticut; Lexington and Chatham, Massachusetts; Seminole, Florida; Philadelphia, Pennsylvania; and Charleston, South Carolina. Family members pictured in photographs include Kathleen’s parents, Joseph P. Kennedy, Sr., and Rose Fitzgerald Kennedy; her siblings, Joseph P. “Joe” Kennedy, Jr., John F. “Jack” Kennedy, Eunice Kennedy, Patricia “Pat” Kennedy, Robert F. “Bob/Bobbie” [sic] Kennedy; Jean Kennedy, and Edward M. “Ted/Teddy” Kennedy; her grandparents, John F. “Honey Fitz” Fitzgerald and Mary Josephine Hannon Fitzgerald; and cousin, Joseph Francis “Joey” Gargan, Jr. Over one hundred friends and acquaintances also appear in photographs, many of whom are identified in original captions. Those who appear more than once within the album include: Edward E. Moore and Mary Moore; Tom Killefer; Torbert "Torb" Macdonald; Richard J. “Dick” Cotter, Jr.; Nancy Van Vleck; Beverly A. “Bev” Bogert; C. Z. “Cizzie” Cochrane; John “Zeke” Coleman, Jr.; Nancy Tenney; Charlotte McDonnell; Francis Huger “Mac” McAdoo, Jr.; Cynthia “Cynth” McAdoo; Kirk LeMoyne “Lem/Leem” Billings; Thomas Henry “Harry” Dixon; John “Johnny” Pyne; Appie Whitney; Eben Pyne; Alison “Allie/Ally” Pyne; Cammann “Cam” Newberry; Constance “Connie” Shepard; James Ayer “Jim” Rousmaniere; Helen MacDonald; Marie Murray; Cyrus Robinson “Cy” Taylor; Nelson Macy, Jr.; William Fuller “Bill” Borland; George Morris Cheston; William Warren “Bill” Scranton; Abbott Widdicombe; Gaspard d’Andelot “Don” Belin; Harriet Bundy “Hattie” Belin; Stanley Rogers “Stan” Resor; Anne Reed; Charles Alfred “Chuckie/Chucky” Pillsbury; Jane "Pil" Pillsbury; Muriel Macy; Demarest "Demi" Lloyd, Jr.; George Houk Mead, Jr.; Richard R. “Dick” Flood; Elizabeth Wayne “Betty” Coxe; Charles “Chuck” Spalding; Inga Arvad; and Mary Dickey. Also pictured are industrialist Henry Ford, British Prime Minister Winston Churchill, and Clementine Ogilvy Spencer Churchill. Original handwritten captions are written in black ink on many of the leaves. This photograph album contains 636 photographic prints and two photo fragments.