The Untold Story: 7 Fascinating Facts About Carole Radziwill's Complex Connection To Ambassador Caroline Kennedy

The relationship between Carole Radziwill and Caroline Kennedy is one of the most intriguing, yet often misunderstood, connections in American high society, blending political royalty with reality television fame. As of the end of 2025, their bond remains rooted in a shared, profound tragedy—the loss of their closest family members—while recent public defenses have brought their familial ties back into the spotlight, proving the Kennedy circle’s loyalty runs deep, even decades later.

This dynamic is not a simple friendship but a complex web of in-law relationships, shared grief, and the enduring legacy of the Kennedy and Radziwill families. The key to understanding their link lies in the tragic story of John F. Kennedy Jr., Carolyn Bessette-Kennedy, and Carole’s late husband, Anthony Radziwill, a narrative that forever intertwined the lives of the former Bravo star and the current US Ambassador to Australia.

Biographies: The Journalist and the Ambassador

To fully grasp the nature of their connection, it is essential to first understand the distinct, yet overlapping, worlds of the two women.

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Carole Radziwill (née DiFalco)

• Born: August 20, 1963
• Notable Career: Emmy and Peabody Award-winning journalist, war correspondent for ABC News, best-selling author (What Remains: A Memoir of Fate, Friendship and Love), and television personality (The Real Housewives of New York City).
• Kennedy Connection: Married to Prince Anthony Radziwill (1994–1999), who was the son of Princess Lee Radziwill (Jacqueline Kennedy Onassis's sister) and Prince Stanisław Albrecht Radziwill. Anthony was John F. Kennedy Jr.'s maternal cousin and best friend. Carole was also the best friend of JFK Jr.'s wife, Carolyn Bessette-Kennedy.
• Current Status (2025): Active writer on her Substack, podcaster, and commentator on culture and politics.

Caroline Kennedy (Caroline Bouvier Kennedy)

• Born: November 27, 1957
• Notable Career: Attorney, author, diplomat, and activist. The only surviving child of President John F. Kennedy and First Lady Jacqueline Kennedy Onassis.
• Diplomatic Roles: Served as the United States Ambassador to Japan (2013–2017) and currently serves as the United States Ambassador to Australia (appointed in 2022).
• Family Connection: Sister of the late John F. Kennedy Jr. and niece of Lee Radziwill.
• Current Status (2025): Serving in her role as the US Ambassador to Australia, continuing the family's legacy of public service.

The Shared Tragedy That Forged a Lifelong Link

The foundation of Carole and Caroline's intertwined lives is built on a series of devastating losses in 1999. This period of intense grief cemented Carole’s place within the periphery of the Kennedy family, even after the passing of her husband.

1. The In-Law Connection Through Lee Radziwill

Carole’s entry into the Kennedy orbit was through her marriage to Anthony Radziwill. Anthony’s mother, Lee Radziwill, was the younger sister of Jacqueline Kennedy Onassis (Caroline’s mother). This made Anthony and Caroline first cousins. When Carole married Anthony, she became Caroline’s cousin-in-law. Although Lee Radziwill passed away in 2019, Carole remains a key figure in the extended family's narrative, often referred to as Lee's daughter-in-law.

2. The Unspoken Bond of 1999

The year 1999 was catastrophic for both women. Carole’s husband, Anthony, passed away from cancer in August 1999 after a long battle. Just weeks earlier, in July 1999, Caroline’s brother, John F. Kennedy Jr., and his wife, Carolyn Bessette-Kennedy (Carole’s best friend), died in a plane crash. Carole was actively involved in the search and recovery efforts for the plane, having been on Martha’s Vineyard at the time. The simultaneous loss of the men closest to them—a husband for Carole, a brother for Caroline—created a shared, unspoken trauma that transcends typical social connections.

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3. The Crucial Distinction: Caroline vs. Carolyn

A persistent source of confusion for the public is the difference between Caroline Kennedy (JFK’s daughter, the Ambassador) and Carolyn Bessette-Kennedy (JFK Jr.’s wife, Carole’s best friend). Carole’s most intimate and well-documented friendship was with Carolyn, a relationship she detailed extensively in her memoir. Her connection to Caroline is familial (in-law) and rooted in the shared experience of being part of the Kennedy/Radziwill inner circle, not necessarily a personal "best friend" bond, though they are known to be cordial and connected.

The Current State: Loyalty, Criticism, and Public Defense

Decades after the tragedies, the relationship between Carole Radziwill and the extended Kennedy family remains a subject of intense public and media scrutiny, especially given Carole’s high-profile reality TV career.

4. Carole’s 2024 Defense of Jack Schlossberg

The most recent and public display of loyalty from Carole to Caroline’s immediate family occurred in 2024. When Caroline Kennedy’s son, Jack Schlossberg, faced public criticism and a media feud, Carole Radziwill stepped in to defend him. She publicly praised Jack, highlighting his intelligence and character, and rebuked the criticism directed at him. This defense, decades after her husband's death, serves as a powerful indicator that the family loyalty and respect remain intact between the two women and their kin.

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5. The Ongoing ‘Embellishment’ Controversy

Despite the genuine connection, Carole’s frequent public references to her Kennedy ties—especially during her time on RHONY—have drawn criticism from some commentators. Some sources have suggested that the Kennedy family has been less than pleased with her public "wrapping herself in the Camelot mystique." This critique often focuses on the idea that her connection is one of marriage, not blood, and that she has "embellished" her proximity to the family for professional gain. This tension is an essential, current-day layer to the relationship.

6. The Unofficial Custodian of the John and Carolyn Legacy

While Caroline Kennedy is the blood relative, Carole Radziwill has become one of the most visible and vocal custodians of the personal, human story of John F. Kennedy Jr. and Carolyn Bessette-Kennedy. She has published essays and participated in documentaries, sharing intimate details about their lives and their final days. This role, which often overlaps with the public memory of Caroline's brother, puts Carole in a unique position as a semi-official historian of a painful chapter in the Kennedy family's history.

7. The Diplomatic Distance of the Ambassador

As the US Ambassador to Australia, Caroline Kennedy maintains a life focused on high-level diplomacy and public service, a world distinctly separate from reality television and memoir writing. While Carole continues to discuss the past in the media, Caroline rarely comments on the family's personal history. This difference in public approach means any current relationship is likely private and respectful, characterized by the vast geographical and professional distance between a reality TV personality/author and a sitting US Ambassador.

The Enduring Legacy of Camelot

The relationship between Carole Radziwill and Caroline Kennedy is a quiet testament to the enduring, though often painful, legacy of the Kennedy family. It is a bond woven from marriage, the shared experience of profound loss, and the public scrutiny that follows anyone connected to the name "Kennedy."

While they may not be seen dining together at the latest New York hotspot, the recent defense of Jack Schlossberg confirms that a deep, foundational loyalty persists. Carole Radziwill is not just a former reality star; she is a woman whose life was irrevocably shaped by the Kennedy family’s greatest triumphs and deepest tragedies, and her connection to Ambassador Caroline Kennedy is a permanent, if complex, entry on the family tree.