Episode 666 Summary: "Winter Dreams" by F. Scott Fitzgerald (with Mike Palindrome) | My Last Book with Lev Grossman

Episode Overview

In episode 666 of The History of Literature, host Jack Wilson, alongside literary aficionado Mike Palindrome, delves into F. Scott Fitzgerald's seminal short story "Winter Dreams." The episode features an in-depth discussion of the story’s themes, character dynamics, and Fitzgerald's literary prowess. Additionally, best-selling novelist Lev Grossman joins the conversation to discuss his novel Bright Sword and reflect on the profound impact of literature on personal growth.

Listener Letter: Ronald’s Reflections (00:15 - 04:57)

The episode opens with Jack Wilson reading a poignant letter from a dedicated listener, Ronald. Ronald, a writer of Arthurian Legends, shares his contemplations on mortality and the enduring influence of literature in his life. He references his recent readings, including John Steinbeck’s interpretation of Thomas Malory's myths, and muses about the finite nature of his literary journey at the age of 82.

Notable Quote:

“I’ll probably have to take it with me when I go. It’ll probably be the last book that I shall ever read.”
— Ronald (00:48)

Jack responds with heartfelt encouragement, emphasizing the universal relevance of reflecting on mortality and the preciousness of time, setting a contemplative tone for the episode.

Discussion with Mike Palindrome: Introducing "Winter Dreams" (04:57 - 14:44)

Mike Palindrome, president of the Manhattan-Based Literature Supporters Club, joins Jack to discuss current literary trends and the group's recent reading selections, including Anthony Powell’s A Dance to the Music of Time and Carl Ove Knausgaard’s Seasons Quartet. Their conversation transitions to Fitzgerald, with Mike expressing his admiration for both Fitzgerald’s novels and short stories.

Jack introduces "Winter Dreams," highlighting its pre-World War II setting and its exploration of the American Dream through the pursuit of love and success. The duo underscores Fitzgerald’s mastery in capturing the fleeting nature of beauty and ambition.

Notable Quote:

“Winter Dreams made me nostalgic for that era... fiction had a pride of place and a centrality in American lives that it doesn't really have today.”
— Jack Wilson (14:33)

Reading: "Winter Dreams" by F. Scott Fitzgerald (14:44 - 73:31)

Jack proceeds to read an extensive excerpt from Fitzgerald's "Winter Dreams," narrating the story of Dexter Green, a successful young man from the Midwest, and his tumultuous relationship with Judy Jones, a captivating and enigmatic socialite. The narrative vividly portrays Dexter’s relentless pursuit of Judy and his struggle to reconcile his ambitions with his desire for love.

Analysis with Mike Palindrome: Themes and Character Dynamics (73:31 - 110:50)

Post-reading, Jack and Mike delve into a comprehensive analysis of "Winter Dreams." They dissect Dexter Green’s character—his ambition, sense of propriety, and inherent sense of inferiority rooted in his modest background. The discussion illuminates Judy Jones as a multifaceted character whose charm masks deeper vulnerabilities and destructive tendencies.

Key Themes Explored:

• The American Dream: Dexter’s quest for success and social elevation.
• Ambition vs. Love: The tension between personal aspirations and romantic entanglements.
• Fleeting Beauty and Youth: The transient nature of attraction and vitality.
• Mortality and Time: Reflections on aging and the passage of time impacting personal fulfillment.

Notable Quotes:

“She always looks as if she wanted to be kissed, turning those big cow eyes on every calf in town.”
— Mike Palindrome (80:39)

“It is rather amazing... he loved her, and he would love her until the day he was too old for loving.”
— Jack Wilson (52:27)

The analysis also touches on the story’s ending, interpreting Dexter’s profound grief not just as sorrow for lost love but as mourning the end of his youthful dreams and the inevitable decline of beauty. Mike and Jack debate the psychological depth Fitzgerald imparts to Dexter, portraying him as a man caught between enduring ambition and unfulfilled emotional desires.

Notable Quote:

“Long ago he said long ago there was something in me but now that thing is gone now that thing is gone I cannot cry I cannot care that thing will come back no more.”
— Dexter Green (73:31)

Guest Segment: Lev Grossman on "Bright Sword" and Literary Impact (110:50 - 116:10)

Best-selling novelist Lev Grossman joins the podcast to discuss his novel Bright Sword, a modern retelling of the King Arthur legend. He reflects on a listener’s poignant question about choosing a last book to read, selecting Samuel Beckett’s Waiting for Godot as his final literary experience. Grossman shares how the play profoundly impacted him during his youth, offering solace and a sense of shared human experience.

Notable Quote:

“I remember that as the first work of literature that I ever experienced where I felt as though nobody was lying to me. It really saved me.”
— Lev Grossman (111:43)

Grossman elaborates on the transformative power of literature, emphasizing its role in providing understanding and empathy, particularly during personal struggles. His insights resonate with the episode's overarching theme of literature’s enduring influence on individuals’ lives.

Notable Quote:

“I could have wept at the wonder of her return.”
— Lev Grossman (112:30)

Conclusion (116:10 - 117:36)

Jack wraps up the episode by thanking Ronald for his heartfelt letter, producer Emma for her contribution in reading "Winter Dreams," and guest Mike Palindrome for his insightful analysis. He also extends gratitude to Lev Grossman for his thoughtful participation. Jack teases future episodes that will explore diverse literary topics, from Edith Maude Eaton's portrayal of Chinese American experiences to the covert roles librarians played as spies.

Closing Quote:

“Waiting for Godot. Off to a great start, aren't we? This year, 2025.”
— Jack Wilson (116:10)

Final Thoughts

Episode 666 of The History of Literature offers a rich exploration of F. Scott Fitzgerald’s "Winter Dreams," blending literary analysis with personal reflections and guest insights. Through thoughtful discussion and evocative storytelling, Jack Wilson and his guests illuminate the complexities of ambition, love, and the inexorable passage of time as depicted in Fitzgerald’s work, while also highlighting the profound personal impact of literature as shared by Lev Grossman.