The $20 Million Secret: Unveiling The Two Legendary Engagement Rings Of Jackie Kennedy

As of December 2025, the enduring fascination with Jacqueline Kennedy Onassis's jewelry collection remains a powerful cultural phenomenon, but no piece sparks more curiosity than her engagement rings. Unlike most public figures who possess one iconic ring, Jackie Kennedy was the recipient of two historically significant—and vastly different—proposals, each marked by a legendary jewel. The first, from John F. Kennedy, was a revolutionary, custom-designed piece that she later had dramatically redesigned. The second, from shipping magnate Aristotle Onassis, was a colossal, rare diamond that became one of the most expensive jewels ever sold at auction, solidifying her status as a global style icon and a woman of immense power. This article delves into the intricate details, the scandalous backstories, and the breathtaking current valuations of these two masterpieces, exploring how each ring reflected a different chapter in the life of America’s most beloved First Lady. From the elegant bypass setting of the Van Cleef & Arpels original to the sheer scale of the 40-carat Lesotho III diamond, these rings are more than just jewels; they are tangible pieces of 20th-century history, celebrity, and unparalleled luxury.

Jacqueline Kennedy Onassis: A Biographical Profile

Jacqueline Lee Bouvier Kennedy Onassis, often simply known as Jackie O, was an American socialite, writer, photographer, and book editor who served as the First Lady of the United States from 1961 to 1963. Her impeccable style, dedication to the arts, and restoration of the White House left an indelible mark on American culture. Her life was defined by both immense privilege and profound tragedy.

• Full Name: Jacqueline Lee Bouvier
• Born: July 28, 1929, in Southampton, New York
• Parents: John Vernou "Black Jack" Bouvier III and Janet Norton Lee
• First Marriage: Married Senator John F. Kennedy on September 12, 1953, in Newport, Rhode Island.
• First Ladyship: Served as First Lady from January 20, 1961, until JFK’s assassination on November 22, 1963.
• Second Marriage: Married Greek shipping magnate Aristotle Onassis on October 20, 1968, on the private island of Skorpios.
• Later Career: Worked as a book editor at Viking Press and Doubleday in New York City.
• Died: May 19, 1994, in New York City, at the age of 64.

The Van Cleef & Arpels Masterpiece: JFK's Diamond and Emerald Ring

The first ring, presented by then-Senator John F. Kennedy in 1953, was a striking departure from the traditional solitaire diamond. It perfectly encapsulated Jackie’s avant-garde style and her desire to stand out, even in the realm of high society jewelry.

The Original 1953 Design: A Bypass Setting

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The ring was commissioned from the prestigious French jewelry house Van Cleef & Arpels. It was an extraordinary choice for an engagement ring at the time, featuring two prominent, intertwined stones set on a distinctive bypass-style shank.

• Main Stones: One 2.88-carat emerald-cut diamond and one 2.84-carat emerald.
• Setting: The stones were set side-by-side, creating an elegant, fluid silhouette.
• Accent Stones: The two main gems were flanked by tapered baguette diamonds, adding to the ring's geometric elegance.
• Initial Value: The ring was estimated to be worth over $1 million at the time of its purchase in 1953, a truly staggering sum for the era.

The Dramatic Redesign of 1961

Shortly after becoming First Lady in 1961, Jackie decided to have the ring dramatically altered, a move that stunned jewelers but demonstrated her confidence in her own aesthetic vision. The original baguette diamonds were replaced with a cascade of marquise-cut diamonds and a variety of other gems, creating a more voluminous, flower-like cluster around the main diamond and emerald. This redesign transformed the piece from a sleek, mid-century design into a more elaborate, glittering statement, cementing its place as one of the most unique and talked-about celebrity engagement rings in history.

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The Lesotho III Diamond: Aristotle Onassis's Colossal Statement

Five years after the assassination of President Kennedy, Jacqueline married Greek shipping magnate Aristotle Onassis in 1968. The ring she received from Onassis was a jewel of such immense scale and rarity that it completely overshadowed her previous ring and became a legend in its own right.

The 40.42-Carat Lesotho III Diamond

Aristotle Onassis presented Jackie with a ring featuring the Lesotho III diamond, a stone cut from the famous 601-carat Lesotho rough diamond. This diamond was a masterpiece from the renowned jeweler Harry Winston.

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• Carat Weight: A staggering 40.42 carats.
• Cut: Marquise cut, a long, slender shape that maximizes brilliance and size.
• Rarity: The Lesotho III was one of only 18 stones cut from the original Lesotho diamond.
• Usage: Due to its immense size and high security risk, Jackie reportedly only wore the ring twice in her lifetime. It was primarily kept locked away in a bank vault.

The Record-Breaking Auction Sale

Following Jackie Kennedy Onassis’s death in 1994, the Lesotho III diamond ring was put up for auction at Sotheby's in New York in 1996 as part of her estate sale. The sale generated intense global media attention, proving the enduring power of the "Jackie O" brand.

The ring was originally appraised for $600,000, but the final sale price shattered all expectations. It sold for an astounding $2.58 million, purchased by a private collector, who was reportedly a high-end jewelry dealer. Adjusted for inflation and the current booming market for celebrity provenance, the estimated current approximate value of a piece with this history and carat weight is often cited to be around $20 million.

The sale of the Lesotho III diamond became a pivotal moment in the history of celebrity auctions, setting a precedent for the astronomical value placed on items connected to iconic figures.

Topical Authority: The Enduring Legacy of Jackie's Jewelry

The story of Jackie Kennedy's two engagement rings provides a fascinating study in contrast and the evolution of personal style. The Van Cleef & Arpels ring from JFK was a reflection of the intellectual, artistic First Lady—a custom, colorful, and sophisticated piece that she felt confident enough to modify to suit her own tastes. It was a jewel for a political dynasty, representing a modern American royalty.

Conversely, the Lesotho III diamond from Aristotle Onassis was pure, unadulterated wealth and status. It was a monumental, museum-quality stone that symbolized her transition from the White House to the world of international high society and immense private fortune. The ring was less about personal style and more about the scale of the commitment and the wealth of her new husband.

Key Entities and Influences:

The rings, and the broader Jackie Kennedy jewelry collection, continue to influence the jewelry and fashion worlds today. The use of vibrant, non-traditional stones like the emerald in an engagement setting is a trend that owes much to her original choice. The marquise-cut diamond, a shape that had fallen out of favor, saw a resurgence in popularity after the high-profile sale of the Lesotho III.

Today, high-end jewelers frequently offer replicas and "inspired by" pieces, ensuring that the legacy of her two legendary engagement rings remains a vibrant part of luxury culture. The rings stand as powerful symbols of two distinct, yet equally influential, chapters in the life of Jacqueline Kennedy Onassis.