4 Books That Explore The Kennedy Family Legacy

Books about the Kennedy Legacy November. Credit: Terri Schlichenmeyer for New Jersey Urban News

Books about the Kennedy Legacy by various authors

c.2026, various publishers $29.99 – $35.00 various page counts

You remember exactly where you were, that end of November, 63 years ago.

Or maybe you don’t. Maybe you were too young, or not yet born, or a long way from being alive then, but you want to know what really happened. So reach for these four great books on John F. Kennedy and the Kennedy legacy….

For the reader who considers the Royal Family and American royalty as two sides of a coin, take a look at “The Kennedys & the Windsors: The Story of Two Dynasties, One Born, One Made” by Caroline Hallemann (Putnam, $35.00). The parallels are there, princesses, kings, queens of commerce and country. Hallemann did her research to show that the Kennedys were considered like homegrown nobility here, back in the day – with just one rival: that of the Royal Family in England. It’s a fascinating look that begs the question: are we still in the midst of royalty that’s similar today?  Find out in this book.

Read that, then don’t miss “Kennedy’s Only Hero: How JFK’s Obsession with Winston Churchill Defined His Presidency” by Joel Nelson (PublicAffairs, $32.00). On one hand, there was Churchill, a lion in Great Britain for decades. But, says Nelson,  few Americans today are unaware of the sway he held over John Kennedy  in America. Through his research, Nelson discovered that, as a young man, JFK devoured all of Churchill’s writing, and those works shaped the man Kennedy became. That’s fascinating stuff, and a great companion to the Hallemann book.

So much has been said about JFK’s politics, but if you can’t get enough about his personal life, then you’ll want “Ladies’ Man: The Careless Heart of John F. Kennedy” by Laurence Leamer (Putnam, $32.00). Leamer’s name may be familiar to readers of Kennedyana; he’s written several books about the family and here, he looks at the many loves of the former president – some known, some unknown. JFK was careful with his love life then – but maybe not careful enough, since we know about his trysts today. But, had he lived, what would those indiscretions have meant today?  Leamer tells… well, if not all, most.

And finally, if you remember the day JFK, Jr. died, then you’ll want to read “The Last Flight: The Untold Story of the Search for JFK Jr. and the Race Against the Atlantic” by Captain W. Russell “Russ” Webster, USCG (Ret.) and Theresa Mitchell Webster (Harper Select, $29.99), a book that takes the Kennedy legacy a few steps farther. 

For five days in 1999, America waited to learn what happened to the late President’s son. This book tells the story in heart-pounding words, in part by the very man who was front-and-center and instrumental at the recovery.

If these books aren’t enough for your history reading, be sure to ask at your favorite library or bookstore. The staffs there can help you find exactly what you want about John Kennedy, Jacqueline or JFK, Jr., or anyone in the family, or any president. 

Because you’re never too young to understand history.