The Prancing Pony Podcast
Episode: 372 – Little Red Dragon
Release Date: May 18, 2025
Hosts: Alan Sisto and Sara (Shieldmaiden of Rohan)

Introduction

The Prancing Pony Podcast welcomes listeners to Episode 372, titled "Little Red Dragon." Hosted by Alan Sisto and Sara Marchese, the episode delves deep into J.R.R. Tolkien's Middle-earth legendarium, focusing on "Unfinished Tales" and the pivotal "Quest of Erebor."

Guest Interview: Ben Hinckley ([02:06] - [10:59])

Alan Sisto introduces today's special guest, Ben Hinckley, an accountant from Minnesota and a dedicated Tolkien enthusiast. Ben shares his journey into Tolkien's works:

• First Encounter ([04:22] - [06:00]): Ben recalls attending a community theater production of The Hobbit at age five, particularly the scene featuring Smaug, which left a lasting impression despite his young age.

  Ben Hinckley ([05:12]): "I picked that up and I didn't put it down until about 4 in the morning on a day before school."

• Deep Dive into Tolkien ([07:30] - [09:00]): Moving to an old stone house in Vermont at age ten, Ben discovered a treasure trove of Tolkien books left by a previous family, reigniting his passion.

  Ben Hinckley ([08:45]): "There's just so much to be found there and so much that's applicable in everyday life."

• Favorites and Memories ([09:15] - [10:00]): Ben cites The Lord of the Rings, particularly Book Four, as his favorite within the legendarium, and Farmer Giles of Ham as his favorite non-Tolkien work. His cherished memory involves reading The Lord of the Rings aloud to his son over nine months.

Sara conducts a lightning round with Ben, touching on his favorite characters, places, and elves, highlighting his choice of Gandalf as his favorite character and Nenithoil in Environs as his preferred Middle-earth location.

Main Discussion: The Quest of Erebor ([11:08] - [128:54])

Exploring "Unfinished Tales" ([11:08] - [32:00])

Alan and Sara embark on an in-depth exploration of "Unfinished Tales," specifically the "Quest of Erebor." They analyze Gandalf's perspective and strategic motivations behind involving Bilbo Baggins in the Dwarven quest to reclaim Erebor from Smaug.

• Gandalf's Strategic Mindset ([15:23] - [16:08]): The hosts discuss Christopher Tolkien’s Manuscript C, which presents a more concise version of Gandalf's plans, contrasting it with earlier versions in "Peoples of Middle-earth."

  Sara ([16:04]): "Economical and tightly constructed in form."

• Gandalf and Saruman's Conflict ([20:34] - [22:10]): They delve into Gandalf's frustration with Saruman, who hinders his plans against Sauron, emphasizing the strategic importance of removing Sauron from Dol Guldur before tackling Smaug.

  Alan Sisto ([21:00]): "He had not thought of them for years. It was not until I got to the Shire and had time to reflect on Thorin's tale that I suddenly remembered the strange chance that had put them in my hands."

Themes of Pride and Greed ([32:00] - [86:52])

The conversation shifts to the pervasive themes of pride and greed in Tolkien's works, using Thorin Oakenshield's character as a focal point.

• Absence of Traditional Families ([46:50] - [50:42]): The hosts reflect on the recurring motif of broken families in Middle-earth, drawing parallels to Tolkien's personal experiences with loss.

  Sara ([49:27]): "Tolkien has a problem with family. So many of the families throughout the legendarium are broken."

• Thorin's Downfall ([65:09] - [86:52]): Alan and Sara analyze Thorin's pride and greed, discussing how these traits lead to his eventual downfall despite Gandalf's warnings.

  Sara ([75:00]): "But that story is about Thorin and how pride and greed overcame him, leading to his death."

• Comparison with Boromir ([104:14] - [105:57]): The duo compares Thorin's tragic end with Boromir's redemption in The Lord of the Rings, highlighting the different ways pride affects these characters.

  Sara ([105:15]): "Pride and greed had overcome all of his better, stronger qualities leaving him a bit of a shell of himself."

Gandalf: Mentor or Strategist? ([121:27] - [126:20])

Addressing a listener's question, Alan and Sara debate Gandalf's role as either a wise mentor or a calculating strategist.

• Dual Nature of Gandalf ([123:36] - [125:00]): They conclude that Gandalf embodies both roles simultaneously—acting as a mentor who deeply cares for his companions while also maneuvering the grand strategy to ensure Middle-earth's safety.

  Sara ([124:28]): "He is perfectly capable of caring about the people with whom he's working and the people for whom he's working at the same time as doing what he must do."

Conclusion and Reflections ([126:20] - [128:54])

As the episode wraps up, Alan and Sara express their anticipation for the next episode, where they will further explore Gandalf's strategies and interactions with Thorin.

• Final Thoughts ([128:54]): The hosts encourage listeners to engage with their Patreon, support their endeavors, and participate in future discussions.

  Alan Sisto ([128:39]): "Tell your friends. Before we get back into the episode, I just want to take a really quick moment to tell you about a project that's got a deadline coming up."

Notable Quotes

• Alan Sisto ([31:14]): "I always think this taking a break is going to help his mind find the answer. I've got a hard problem to face. Put it away, do something else and let the back of my brain sort of process that in the background."

• Sara ([164:20]): "He is the best of Boromir. I mean, sometimes it's somebody else like Gimli when they're going through the paths of the dead. But most of the time it's Sam."

• Alan Sisto ([87:04]): "Look after your darling. I know your fame, Thorin answered. I hope it has merited."

Key Insights

1. Gandalf's Strategic Influence: Gandalf's involvement in the Quest of Erebor is not merely that of a mentor but also a calculated strategist aiming to influence the broader events shaping Middle-earth, such as combating Sauron.

2. Themes of Pride and Greed: The episode underscores how pride and greed are central to the downfall of characters like Thorin, echoing similar themes in Tolkien's work and reflecting deeper narrative patterns.

3. The Role of Chance vs. Providence: Alan and Sara explore the delicate balance between chance encounters and a sense of providence guiding events in Tolkien's mythology, questioning how much is deliberate strategy versus fate.

4. Broken Families as a Narrative Device: The recurring motif of broken families in Middle-earth serves to highlight themes of loss and continuity, possibly mirroring Tolkien's personal experiences with grief.

5. Duality of Gandalf's Character: Gandalf embodies both a caring mentor and a shrewd strategist, showcasing Tolkien's ability to create multifaceted characters who operate on both personal and grand scales.

Conclusion

Episode 372 of The Prancing Pony Podcast offers a profound exploration of Gandalf's role in the Quest of Erebor, intertwining character analysis with thematic discussions on pride, greed, and fate. Through engaging dialogue and insightful commentary, Alan and Sara provide listeners with a deeper understanding of Tolkien's intricate world, setting the stage for future episodes that promise to unravel more of Middle-earth's enigmatic threads.

Join the Conversation:
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