
Jackie Kennedy's Secret Confessions: The Hidden Heartaches of America's Beloved First Lady

Jackie Kennedy was the epitome of grace, elegance and quiet strength.
May 26 2025, Published 6:00 a.m. ET
Jackie Kennedy Shared Her Secrets With One Confidant

Jackie Kennedy met Father Joseph Leonard when she was on a trip to Ireland. She was 21 and he was 73.
Jacqueline "Jackie" Kennedy, America's beloved first lady, captivated the world with her poise, beauty and unwavering composure. But behind the polished smile and iconic style was a woman grappling with private heartaches, loneliness and suspicions she dared share with only one confidant — an elderly Irish priest, Father Joseph Leonard.
"It's so good in a way to write all this down and get it off your chest — because I never do really talk about it with anyone — but poor you has to read it!" she wrote.
In 1950, 21-year-old Kennedy traveled to Ireland and met Father Leonard, a kind, compassionate soul and a decorated World War II veteran, who saw beyond the socialite facade to the vulnerable heart beneath. Over the next 14 years, her 33 letters — written in an easy, flowing style — became her sanctuary. To him, she poured out fears and confessions she never dared reveal to anyone.
She shed her armor, confessing her deepest doubts, her despair and her search for faith amid the storms of life. She always ended them with terms of endearment: "Bushels, barrels, carts & lorry loads of love to You — Jacqueline XXXOO."
She had to explain to Father Leonard that the Xs and Os "mean hugs & kisses" and told him: "Now you know what they mean so you don't have to reveal my indiscretions to other women!"
Jackie Kennedy Fell in Love With John Kennedy

She met Father Joseph Leonard only once again years later, but she poured her heart out in her letters.
In one 1952 letter, she revealed how she nearly didn't become a Kennedy, writing that she was "so terribly much in love" with her then-fiancée, New York stockbroker John Husted.
But by July of the same year, she confessed that another man had caught her eye.
"I think I'm in love with — and I think it would interest you, John Kennedy, he's the son of the ambassador to England, the second son, the oldest was killed. He's 35 and a congressman," Jackie wrote. "Maybe it will end very happily or maybe, since he's this old and set in his ways and cares so desperately about his career, he just won't want to give up that much time to extracurricular things like marrying.''
But he did ask her to marry him. She later told Father Joseph she had foreseen, and already excused, his infidelities by comparing them to her father, John "Black Jack" Bouvier. Her parents had divorced when she was 10, but she was fiercely devoted to him.
Jackie's new husband, has "so strong a personality — like his father [Joseph Kennedy], who has so overpowered Mrs. [Rose] Kennedy he doesn't even speak to her when she's around and her only solace now is her religion ... I don't think Jack's mother is too bright. She would rather say a rosary than read a book."
Jackie Kennedy Compared Her Husband to Her Father

Jacqueline Bouvier married Jack Kennedy on September 12, 1953.
Later, Jackie confessed that her "frighteningly ambitious" husband was also like "my father — loves the chase and is bored with the conquest — and once married, needs proof he's still attractive, so flirts with other women and resents you. I saw how that nearly killed Mummy."
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Jackie Kennedy Faced Tragic Losses

Jackie Kennedy was very much in love with her philandering husband — and found a way to look past his cheating.
Jackie's heartbreak deepened with the tragic loss of her stillborn daughter Arabella in 1956. The grief she masked with grace in public came pouring out in her private confessions. She wrote that she even grappled with her own belief in the Lord.
She revealed, "I am so bitter against God." But, she told Father Joseph, she could "see how sadness shared brings married people together."
She gave birth to daughter Caroline in 1957 and son John in 1960, but her son Patrick died at two days old, and her husband was assassinated three months later. Jack's death completely shattered her.
In the aftermath of that horror, Jackie confessed, "I would have rather lost my life than lost Jack," she wrote on black-edged mourning paper. "God will have a bit of explaining to do to me if I ever see Him. How can He let such cruelty happen?"
After the worst of her grief had passed, she had worked out a private consolation for his death, writing, "I think God must have taken Jack to show the world how lost we would be without him — but that is a strange way of thinking to me. I have to think there is a God — or I have no hope of ever finding Jack again."
Jackie Kennedy Kept Her Heartbreaks a Secret

After all the pain and heartache, Jackie went on with her life.
Jackie never let the world see her deepest wounds. In public, she was stoic, regal, the perfect first lady. But in her letters, she was achingly human — a woman broken and mending, doubting and believing, falling and rising again.
Father Joseph died in 1964 at 87, and the letters were discovered in an old safe at All Hallows College in Dublin, where he had taught. They were quietly set for auction. Select individuals glimpsed the raw truth within them, but the identity of their current owner remains shrouded in secrecy. Which is for the best, said insiders, because Jackie valued privacy above all.
Her confessions were a testament to her inner world, one marked by profound love, unthinkable loss and a strength that defied the ages.
Jackie Kennedy Died in 1994

She was diagnosed with non-Hodgkin lymphoma before her death.
When Jackie died in May 1994 at 64, an obituary described her as "a quintessentially private person, poised and glamorous but shy and aloof." She "never created an oral history," and "her silence about her past, especially about the Kennedy years and her marriage to the president, was always something of a mystery."
But her private confessions to Father Joseph — which revealed the depth of her darkest hopes, fears and pain — gave people today a glimpse of the real woman beneath the public persona — resilient, heartbroken and fiercely human.
The whereabouts of Father Joseph's letters to Jackie — if they still exist — have never been discovered.