The Five Most Valuable F. Scott Fitzgerald Books
Discover the top five most valuable F. Scott Fitzgerald books ever sold at Sotheby's, from rare first editions to Fitzgerald’s handwritten manuscripts.
When F. Scott Fitzgerald published The Great Gatsby in 1925, he cemented his status as one of the most important voices of the Jazz Age. His works, capturing the opulence, excess, and tragic disillusionment of the Roaring Twenties, have become some of the most revered in American literature. While Fitzgerald struggled financially during his lifetime, his books have since become some of the most sought-after and valuable modern literary collectibles. Below are five of the most expensive F. Scott Fitzgerald books ever sold at Sotheby's.
5 Most Valuable F. Scott Fitzgerald Books
The Great Gatsby, New York, 1925, First Edition, Original Dust Jacket, Unrestored, 377,000 USD
The Great Gatsby, F. Scott Fitzgerald’s 1925 masterpiece, is one of the most sought-after works in American literature, and its first edition in an original, unrestored dust jacket is a true collector’s treasure. While the novel initially struggled to match the commercial success of Fitzgerald’s earlier works, its reputation has since eclipsed almost all other 20th-century American novels, solidifying its status as a defining work of the Jazz Age. The dust jacket, designed by Francis Cugat, has become as legendary as the book itself—its striking celestial imagery forever tied to the novel’s themes of longing and illusion. Fitzgerald famously wrote to his editor, Maxwell Perkins, imploring him to reserve a copy of the jacket, claiming he had “written it into the book.” Due to the fragile nature of the jacket, most surviving copies have undergone significant restoration, making a wholly unrestored example an extraordinary rarity.
In April 2024, the highest price ever realized for a Fitzgerald book at auction was achieved when a first edition of The Great Gatsby with its original, completely unrestored dust jacket sold for an astounding $377,000. This exceptional copy retained the jacket’s vibrant blue field and crisp white lettering, even on the notoriously fade-prone spine. With only minor wear and no restoration, it remains one of the finest known examples, offering a rare glimpse into how the book would have appeared upon its release nearly a century ago. The sale reaffirmed Gatsby’s enduring legacy, not only as a literary landmark but also as a pinnacle of book collecting. Much like Gatsby’s own pursuit of an unattainable dream, collectors continue to chase the ultimate prize—an untouched first edition in its original form, a symbol of American literary history at its most iconic.
The Great Gatsby, First Edition, Original Dust Jacket, Inscribed to Zelda’s Sister and Her Husband, 336,000 USD
A first edition of The Great Gatsby inscribed by F. Scott Fitzgerald to his sister-in-law, Rosalind Sayre Smith, and her husband, Newman "Capitan" Smith, stands as one of the most remarkable association copies of the novel. In June 2024, this unique copy of The Great Gatsby achieved a remarkable $336,000 at auction. The book, complete with its first-state dust jacket featuring Francis Cugat’s iconic design, offers an intimate connection to Fitzgerald’s personal life and the family tensions that shaped his later years. The inscription, penned in June 1925, just months after Gatsby’s publication, reflects a time when Scott and Zelda were immersed in the glamour and excess of the Jazz Age, while Rosalind remained a skeptical observer. Known for her disapproval of Fitzgerald’s drinking and his tumultuous relationship with Zelda, Rosalind would later become one of his harshest critics, particularly as Zelda’s mental health deteriorated. The deep personal history embedded in this copy, combined with the novel’s enduring literary legacy, makes it an extraordinary artifact of American literature.
This sale reaffirmed the novel’s place as a cornerstone of book collecting, with inscribed first editions commanding ever-increasing interest. This particular copy’s significance extends beyond its monetary value, offering a glimpse into the fraught relationships that shaped Fitzgerald’s later work. Elements of Rosalind and Newman’s disapproval of Scott and Zelda would find their way into Babylon Revisited, one of Fitzgerald’s most poignant short stories, cementing the Sayre family's complex and lasting influence on his literary career.
The I.O.U., Autograph Manuscript Signed, 194,500 USD
In June 2012, an unpublished short story manuscript titled The I.O.U. surfaced at auction, drawing significant attention from collectors. When The I.O.U. crossed the auction block at Sotheby’s New York on June 15, 2012, it achieved an impressive $194,500. Written around 1920, the manuscript featured Fitzgerald’s autograph draft in pencil, complete with revisions, alongside a typescript version. Accompanying the manuscript was a note from Fitzgerald’s literary agent, Harold Ober, providing a brief synopsis of the story. As an unpublished work from a pivotal period in Fitzgerald’s career—just before This Side of Paradise catapulted him to fame—The I.O.U. stands as a rare and valuable piece of his literary legacy.
This remarkable price underscored the continued demand for Fitzgerald’s handwritten materials, particularly those predating his rise to literary stardom. As one of the few unpublished Fitzgerald manuscripts in private hands, The I.O.U. represents an important chapter in the author’s early career, capturing his evolving narrative style and the themes that would later define his most celebrated works. The sale reaffirmed Fitzgerald’s lasting appeal, proving that even a century after he first put pen to paper, collectors remain eager to own a piece of his genius.
Tender Is the Night (New York, 1934, Presentation Copy, Inscribed to Zelda’s Psychiatrist), 175,000 USD
A rare signed copy of Tender is the Night fetched $175,000 at auction in April 2017, distinguished by Fitzgerald’s cryptic inscription: "For you 'Marg Mortimer' or 'Edna Carlyle' or whatever you call yourself now—Seriously, For Hope from F. Scott Fitzgerald." This third printing of the first edition offers a personal glimpse into the author’s world, reflecting themes of identity and reinvention. Tender Is the Night, Fitzgerald’s final completed novel, draws heavily from his own experiences, particularly the unraveling of his marriage to Zelda and his disillusionment with the Jazz Age.
The novel’s exploration of decadence and decline is epitomized by Fitzgerald’s use of alcohol as both a symbol of escape and destruction. One of its most evocative lines—"The cocktails were like fire. They burned through the drinkers, quick and hot, making them laugh and forget themselves, until the party took on a life of its own."—captures the fleeting euphoria and inevitable downfall of its characters. This well-loved, inscribed copy serves as a tangible link to Fitzgerald’s world, making it a prized artifact for collectors.
This Side of Paradise (New York, 1920, First Edition, Dust Jacket), 161,000 USD
This Side of Paradise, F. Scott Fitzgerald’s debut novel, signaled the arrival of a literary voice that would come to define the Jazz Age. A first edition with its original dust jacket, an exceptionally rare survival, sold for $161,000 in January 2014. The dust jacket, unrestored and retaining much of its original gloss, is a key factor in the book’s value, as early 20th-century jackets were often discarded or damaged over time. This novel, chronicling the aspirations and disillusionments of a young Princeton graduate, established Fitzgerald’s reputation and captured the spirit of a generation intoxicated by youth, wealth, and the pursuit of success.
Much like The Great Gatsby, where its now-iconic dust jacket significantly impacts value, the design of This Side of Paradise plays an important role in its desirability among collectors. Fitzgerald was known to take inspiration from visual elements, famously incorporating Gatsby’s cover art, an ethereal pair of eyes floating above a cityscape, into the novel’s narrative as the optometrist’s billboard. This first edition’s remarkable condition and rarity made it a prize at auction, cementing its status as a touchstone of early 20th-century American literature.
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