Two iconic dynasties—the Kennedys and the Windsors—whose glamour and ambition defined an era.
** For fans of FX’s new Ryan Murphy limited series Love Story. **
For nearly a century, two families an ocean apart have captured the world’s collective imagination: the British Windsors and the American Kennedys. Much ink has been spilled on their individual trysts, tragedies, and triumphs over the years, but no one has examined their powerful and intertwined legacies. Until now.
In The Kennedys and the Windsors, acclaimed journalist Caroline Hallemann unearths the story of two iconic families whose lives, ambitions, and respective reigns have mirrored each other in surprising ways. Through rich archival research and fresh interviews from insiders on both sides of the Atlantic, Hallemann reveals how an upstart Irish Catholic family with little access into elite New England society came to host dinner parties for a King and Queen, and forge an eventual path to the White House. In the process, she draws out some startling parallels between the two families: the style icons Princess Diana and Carolyn Bessette-Kennedy (both tragically gone too soon), the frustrated “second sisters” Princess Margaret and Lee Radziwill, the scandal-plagued next generation of Robert F. Kennedy Jr. and the man formerly known as Prince Andrew, and the current generation’s shared struggle to figure out what a monarchy (actual or imagined) means in the twenty-first century.
From Queen Elizabeth’s coronation to President Kennedy’s historic London visit, from JFK Jr.’s shocking death to Prince Harry’s decisive break with his family, Hallemann traces the key moments in the lives of these two dynasties through a fresh and fascinating lens, showing how they have intersected over the generations in ways that not only shaped their images and legacies, but history itself.
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Caroline Hallemann is the Digital Director of Town & Country magazine, where she writes about culture, society, entertainment, and the world of the rich and powerful. Her work has often focused on the British monarchy and the closest thing America has to a royal family: the Kennedys. She lives in Nashville, Tennessee.
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Chapter 1
The Kennedys at Court
Joseph P. Kennedy was an unusual choice for ambassador to the Court of St. James's in 1937. An Irish Catholic Bostonian, he and his family had always been on the outskirts of WASPy New England society.
Joe's wife, Rose Fitzgerald Kennedy, once described Boston as being made up of two separate communities. One of them was Protestant and English, essentially constituting the descendants of the original colonists-"proper Bostonians," or Boston Brahmin as they were sometimes called. "With the advantages of inherited wealth and status and close-knit interfamily ties, they controlled the banks, insurance companies, the big law firms, the big shipping and mercantile enterprises, and almost all the usual routes to success, and thus were a self-perpetuating aristocracy," Rose explained in her memoir, Times to Remember. It was a "closed" society.
The other predominant group in Boston was the Irish Catholics, many of whom were the descendants of those who had fled Ireland during the Great Hunger of the mid-1800s. "Between the two groups feelings were, at best, suspicious, and in general amounted to a state of chronic, mutual antagonism," Rose wrote, explaining that this discord had "stemmed from the ancient unhappy relationship between England and Ireland," and had been sustained across not only geography but also generations. Irish Catholic Bostonians often gained clout through politics. At least, that's how it worked for Rose's family. She was the daughter of John "Honey Fitz" Fitzgerald, a colorful "pixielike" man, who rose to prominence as Boston's mayor and, later, used his influence in the local Democratic Party to give his grandson (his namesake, John Fitzgerald Kennedy) a leg up. The Kennedys were already at the center of Boston's Irish community by the early twentieth century. But with Joe's appointment as ambassador, they found themselves navigating the complexities of the English upper class. It was not always easy.
Then, as now, many of the cushiest ambassadorships were given to campaign supporters. Joe's was one such appointment; the position was granted as a thank-you of sorts for his support of President Franklin D. Roosevelt's 1936 reelection campaign, despite his complete lack of relevant diplomatic experience. After attending Harvard University, Joe had built his fortune first as a banker and then as a producer in Hollywood.
While many have alleged that Joe made millions transporting and selling alcohol during the Prohibition era, a rumor that began during his lifetime, there's no credible evidence of that sort of illicit behavior. But as historian Daniel Okrent put it in his book Last Call: The Rise and Fall of Prohibition, "One cannot prove a negative." And the allegations are rooted in a kernel of truth. As the amendment to repeal Prohibition was gaining popularity in the fall of 1933, Joe traveled to England with James Roosevelt, the son of FDR. While in the UK, they met with the managing directors of the conglomerate Distillers Company, securing the rights to become the sole American importer of Dewar's and Haig & Haig whiskey and Gordon's gin. Joe had already procured a medicinal liquor permit, as well as warehouse space for the alcohol, and so they prudently imported the goods in November, preparing for the day when imbibing alcohol was once again legal in the US. They were ready for the raucous celebrations on December 6, 1933. However, as this story was repeated, the legality of Joe's actions was left out, and so, as Okrent put it, "from such acorns, nourished by a lifetime's accumulation of rumors, enemies, and vast sums of money, arose the widely accepted story of Joseph P. Kennedy, bootlegger."
With another term secured for FDR, Joe had his eye on another post entirely-that of secretary of the treasury-but that simply wasn't an option. "Father was not going to remove Henry Morgenthau from office. Father did not tell Joe in so many words, but in time it became clear to him," James Roosevelt wrote in his memoirs, noting that while the treasury secretary post was off the table, his father did want to give Joe something in return for his loyalty.
"We've got to do something for old Joe, but I don't know what," FDR told his son. "He wants what he can't have, but there must be something we can give him he'll be happy with."
There was one other job Joe would be willing to consider. "I'd like to be ambassador to England," he told James one evening. If status for his family was what he was seeking, he would have been hard-pressed to pick a better position. The list of ambassadors up to that point included many successful politicians, including five future presidents (John Adams, James Monroe, John Quincy Adams, Martin Van Buren, and James Buchanan) as well as numerous notable businessmen.
"He wanted to build as high a platform as possible from which his children could be launched. He wanted them to start out with every possible advantage, advantages that he himself hadn't had," Jack Kennedy's longtime close friend Kirk LeMoyne "Lem" Billings would later say. "I don't think there's any question about it, the post of the American Ambassador to the Court of St. James's couldn't do anything but help build prestige for the Kennedy family."
When James Roosevelt relayed Joe's ambition to his father, FDR allegedly "laughed so hard he almost toppled from his wheelchair." Yet, Joe Kennedy had a way of getting what he wanted. And in this case, Roosevelt was easily convinced. After all, sending Joe across the ocean made it far more difficult for him to interfere in politics at home. Plus, Roosevelt knew that Joe had deep pockets and would be willing to entertain on his own dime. Kennedy biographer Susan Ronald also suggests that the idea of Joe as ambassador "appealed to Roosevelt's mischievous sense of humor, picturing an Irish Catholic in the bastion of Anglicanism." And so, on February 18, 1938, Joe Kennedy was sworn in as the US ambassador to Great Britain by Supreme Court Justice Stanley Reed, as President Roosevelt looked on. A few days later, on February 23, he boarded the SS Manhattan and set forth across the Atlantic.
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From the moment a Kennedy stepped foot in London, the British press was fascinated by the family. Reporters captured Joe’s arrival in Plymouth, and they were there as he saw his new residence in London, a six-story Beaux-Arts-style property just off Hyde Park. He had several American creature comforts sent over to immediately make the fifty-two-room mansion feel more like home: candy from a specific store on Cape Cod, Maxwell House coffee, toiletries including Nivea and Jergens lotions, Cheracol cough syrup, and dozens of cans of New England clam chowder. The cellar was stocked with champagne for hosting, and he had arranged to borrow works of art from William Randolph Hearst’s castle in Wales to adorn the walls. He also took note of how close 14 Prince’s Gate was to “Rotten Row,” a specific area in the park where the upper class were often seen horse riding.
After much conversation about whether or not Joe would wear the customary knee breeches at court (he eventually opted for long trousers, bucking British tradition in something of a faux pas), he became a "full fledged" ambassador by presenting his letter of credence to King George VI on March 8, 1938. "The coaches, with their scarlet-coated drivers and footmen, came for us at the Embassy a little after eleven," Joe wrote in his diary. "The show at Buckingham Palace was set up to expectations, and I chatted informally with the King for five minutes. I found him charming in every way."
A few days later, Rose arrived with her second-eldest daughter,...
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