New Book Delves Into JFK's Charisma, Insatiable Affairs — and His Last Moments with Baby Son Patrick

In Incomparable Grace, Mark Updegrove examines how the president's reckless extramarital romances impacted his marriage and how the loss of his second son drew him and his wife closer than ever

US President John F. Kennedy (1917 - 1963) addresses a press conference, circa 1963.
John F Kennedy. Photo: Arnold Sachs/Archive Photos/Getty

The personal allure of John F. Kennedy — strong as a magnet — is, for many, what sets him apart in the history books.

A charismatic orator, Kennedy's charm often masked his flaws (and fed his penchant for flirtation). But as a new book details, behind the appeal of the young senator-turned-president was a man who faced a steady stream of challenges before his assassination in 1963.

In Incomparable Grace: JFK in the Presidency, published Tuesday, Mark K. Updegrove writes of how the White House and Kennedy's own personal trials transformed him before his sudden death less than three years into his term in office, the period that would come to be known as "Camelot," a mythical creation designed by his widow to help ensure his legacy.

"Though fortune had smiled generously on John Kennedy throughout his forty‐six years, tragedy always patiently lay in wait," Updegrove writes.

Indeed, the glamour of "Camelot" masked a more complicated reality of triumphs marred by personal failings. The pattern would, after Kennedy's death, come to be seen as a curse that touched many others in his family — though some of it was of Kennedy's own doing, Updegrove writes.

Even long after death, Kennedy's reputation as a "rampant and reckless womanizer" has thrived. But according to Updegrove, his passion for extramarital affairs wasn't something that stemmed from his presidential power. It was something he learned at an early age.

"In the hypercompetitive, testosterone‐infused Kennedy family, unbridled womanizing seemed as much about keeping score as it did the thrill of the conquest," the author writes.

Updegrove expounds on this idea elsewhere in his book, writing that "to be sure, JFK had grown up learning philandering at the feet of the master, Joe Kennedy, Sr."

But as he grew older, got married, had children and even after he was elected president, the younger Kennedy's cheating continued.

Rumors and stories of this dogged him for years beyond his 1963 assassination and, as Updegrove writes, went beyond mere habit.

John F. Kennedy and Jackie sit together in the sunshine at Kennedy's family home at Hyannis Port, Massachusetts, a few months before their wedding.
John F Kennedy and Jackie. Bettmann/Getty

"His sexual appetite was ramped up by daily cortisone shots for his back, and was fed all too readily by friends and acolytes eager to indulge him by finding willing partners: socialites, movie stars, White House secretaries and interns, and high‐end prostitutes—anyone would do," Updegrove writes in Incomparable Grace.

"Anyone" included starlets — among them Marilyn Monroe — and others who never publicly confirmed their reported dalliances with President Kennedy.

Updegrove, the head of the LBJ Foundation and a presidential historian for ABC News, spoke to a number of Kennedy confidantes while researching his book. Among them was actress Angie Dickinson, who recalled Kennedy's "charisma" and "drop dead" good looks. (Asked about an affair with Kennedy, as has been long whispered, Dickinson told the author: "We had a lot of fun thinking about it.")

In his book, Updegrove also gives his answer on a persistent question: First Lady Jacqueline Kennedy knew about her husband's proclivities and "accepted" that part of his life, he writes — but that surely didn't make it any easier for the woman who, in public, exuded grace.

Five years before his election as the 35th president, Kennedy's mixed record as a husband and father had come to a head, Updegrove writes: "In 1956, hearing three days after the fact that Jackie had given premature birth to a stillborn daughter, Arabella, Kennedy was in Capri [off the coast of Italy], carelessly enjoying a European holiday cruise on the Tyrrhenian Sea, where he intended to stay. It fell to Bobby to tend to the situation back home, comforting Jackie and arranging for the burial of the infant."

It wasn't until the then-senator was admonished by Florida colleague George Smathers (who warned him that remaining in Capri could cost him a future election) that Kennedy returned home.

A similar tragedy would befall the couple during Kennedy's White House tenure with the birth of their second son, Patrick.

Patrick was born on a somber day for his dad, who 20 years prior had been rescued when his World War II patrol torpedo boat was cut in half by a Japanese destroyer.

The date — Aug. 7, 1963 — proved to be something of an omen, with Patrick coming five-and-a-half weeks early. Updegrove writes that President Kennedy was rushed aboard Air Force One from Washington, D.C., to meet his wife at Otis Air Force Base on Cape Cod in Massachusetts, "where a suite had been prepared for the first lady in its modest hospital."

The little boy was born while the president was still en route, at 12:52 p.m, with Updegrove believing that "as [he] rushed to New England, his mixed record as a husband and father surely must have weighed on his mind."

Kennedy was able to see his son only briefly before Patrick was "flown by helicopter to Children's Hospital in Boston and placed in a steel hyperbaric chamber designed to keep his lungs open," the book details.

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Days later, while sleeping in the hospital waiting room, Kennedy was awoken by a Secret Service agent with the news that his child's health was fading.

The next few moments were poignant, offering a glimpse of the humanity of the man later obscured by myth.

"Patrick was wheeled into the corridor where Kennedy, sitting in a wooden chair and dressed in a surgical cap and gown, kept vigil," Updegrove writes. "As the baby's heart stopped beating at 4:19 a.m., his father held his small fingers in his own. 'He put up quite a fight,' he said in a whisper. 'He was a beautiful boy.' Kennedy then retreated to the quiet privacy of a hospital boiler room, where he sobbed over the loss."

Seven years after President Kennedy had disappeared in the wake of the death of Arabella, he bore the responsibility of informing his wife of another loss.

After returning to Cape Cod from Boston, Updegrove writes, Kennedy "fell to his knees, his arms around [the first lady], as tears streamed down his face. It was only the third time Jackie had seen her husband cry."

As the two held one another, she told him, "There's one thing I couldn't stand. If I lost you . . ."

The loss instilled in the president "a wistfulness and greater sense of mortality" and strengthened the Kennedys as a couple, according to Updegrove. It would also, most fatefully, inform the first lady's fortitude "in the unimaginable days ahead in late November."

Kennedys and Johnsons
From left: President John F. Kennedy and a bouquet-carrying Jacqueline Kennedy arrive at Love Field in Dallas on Nov. 22, 1963, on a campaign tour with Vice President Lyndon Johnson and Lady Bird Johnson (rear). Art Rickerby/The LIFE Picture Collection via Getty

Indeed, as has been recounted countless times before, Nov. 22, 1963, seemed "promising" for the Kennedys.

The pair had flown to Texas to appear in a parade, held on a street lined by 150,000 people. But the idyllic procession was shattered by three shots ringing out in rapid succession, President Kennedy's body collapsing with the impact of a shot to his arm and another to the back of his head.

Once in the hospital, his wife, motionless, "remained by his side to the last, her eyes never leaving his."

The slaying immortalized the man, creating a legacy that Updegrove writes "has become magnified over the years by the Camelot veneer." More than anything, though, it led so many to wonder "what might have been had he not been cut down in his prime."

Incomparable Grace is out now.

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