Pity, Power, and Tolkien's Ring: To Rule the Fate of Many

by Thomas P. Hillman

Illuminating the central struggle in The Lord of the Rings to deepen understanding of the whole of Tolkien’s legendarium In this remarkable work of close reading and analysis, Thomas P. Hillman gets to the heart of the tension between pity and the desire for power in J. R. R. Tolkien’s The Lord of the Rings. As the book traces the entangled story of the One Ring and its effects, we come to understand Tolkien’s central while pity is necessary for destroying the Ring, it cannot save the Ring-bearer from the Ring’s lies and corruption. In composing The Lord of the Rings, Tolkien explored the power of the Ring and the seeming powerlessness of pity. All the themes his mythology had come to encompass―death and immortality, fate and free will, divine justice and the problem of evil, power and war―took on a new dimension in the journey of Frodo Baggins. Hillman’s attention to specific etymologies and patterns of words used in the text, complemented by his judicious use of Tolkien’s letters, earlier drafts of the novels, and Tolkien’s essays, leads to illuminating and original insights. Instead of turning his interpretation to allegory or apologetics, Hillman demonstrates how the story works metaphorically, allowing Tolkien to embrace both Catholic views and pagan mythology. With this fresh understanding of familiar material, Pity, Power, and Tolkien’s Ring will ignite new discussions and deeper appreciation among Tolkien readers and scholars alike.

Genres: Nonfiction

320 pages, Paperback

Published December 19, 2023

Reviews

[Katherine Sas · Rating 5 out of 5]

Outstandingly thoughtful and profound. Well done, Tom. I will be recommending this book to anyone who ever suggests that Tolkien doesn’t care about subtle characterization.

[Scott Wise · Rating 5 out of 5]

This book can be challenging. It is extremely detailed and in-depth. Its audience is those who want to go deep into the story, characters, and themes contained in The Lord of the Rings. However, if that is you, this book is one of the most thorough journeys through what is going on behind the text. It is not a light read, but it does follow details of theme and characterization all the way down to word choice, drafts, and intent without losing the heart of the story. In fact, putting that heart on full display for those willing to go on the journey with the author.

[Mythlee · Rating 5 out of 5]

The author is a classicist who has spent a half-century reading and re-reading The Lord of the Rings. The result is a thoughtful and engaging close reading and argument, with plenty of wit and Shakespearean allusions. What's not to like?

[Clare Moore · Rating 5 out of 5]

An ambitious book that explores the theme of pity throughout the entirety of The Lord of the Rings by focusing on Frodo and Gollum primarily. It also touches on material from The Hobbit and The Silmarillion and other works by Tolkien, but Frodo’s pity for Gollum and its relationship to the One Ring is the main through line of the book. Some excellent interpretations and close readings make this book well worth the read for Tolkien scholars and fans.

[Jenna (Falling Letters) · Rating 4 out of 5]

Brief thoughts originally published 11 January 2026 at Falling Letters.

One of my final reads of 2025, this book inspired me to set a goal to read more Tolkien in 2026. While it was a little dense for me, I loved this close reading of The Lord of the Rings. More like this please! Tom follows the chronological journey of the One Ring through The Lord of the Rings by exploring the influence of the Ring on various characters, as well as characters’ own reactions to both the Ring and to those influenced by the Ring. One of my favourite chapters which I found particularly eye-opening explores Frodo’s actions from Emyn Muil to the Dead Marshes from a perspective I had never considered before.

[Vincent Waldron · Rating 4 out of 5]

In Pity, Power, and Tolkien's Ring, Thomas Hillman did a deep dive on one of the most important themes in the Lord of the Rings (LoTR). He painstakingly analyzed the text of the LoTR from the first chapters through to the bitter sweet end. Along the way, he brought in quotations from Tolkien's letters and other works of Tolkien.

"The real theme for me is about something much more permanent and difficult. Death and Immortality: the mystery of the love of the world in the hearts of a race "doomed" to leave and seemingly lose it, the anguish in the hearts of a race "doomed" not to leave it, until its whole evil-aroused story is complete." (Tolkien Letters no. 186)"

Tolkien used the word "Pity" many times throughout the LoTR. It is clear from early on -- in the Shadow of the Past -- that Gandalf, at least, believed that those whose hearts were compassionate would be protected from the worst effects of the Ring. Yet, even there, the Ring could turn that desire to do good to something evil.

"The desire that one would seek to gratify through the Ring -- whether it is Gandalf's "desire of strength to do good," Galadriel's and Boromir's desire to defeat evil and to rule, or even Frodo's to destroy the Ring itself and save the Shire -- is the substance, the mass, as it were, on which the Ring exerts its pull."

The point is that the Ring is corrupting. For someone who desired power to do good, it would seem to offer them the power to fulfill those desires. The only real solution from the standpoint of the mighty was to turn down the power the Ring offered.

"This, I think, is a problem faced often but by no means exclusively by scholars who examine the Lord of the Rings from a Christian perspective, not always successfully. By focusing too narrowly on how Frodo suffers and sacrifices to save the Shire and destroy the Ring, we can develop a simple image of him as saintly or even messianic. Yet, the longer Frodo has the Ring and the closer he comes to the source of its power, the more both darkness and light grow within him and advance his weary feet. Without the chiaroscuro the shadow of his faults brings to his nobility, our understanding can only be incomplete."

There is a long discussion of Tom Bombadil and the seeming lack of the Ring to have power over him. Since Tom has no desire to rule over anything, the Ring has no hold over him.

"Because he is his own master, the Ring has no power over Tom; and he is his own master because the desire to dominate or possess is not in him."

Later on, Hillman posits Shelob as almost an anti-Bombadil -- a creature fully evil, but indifferent to power. Instead, she only desired to consume and grow her own destructive essence.

When Frodo pulled the Lady's Glass from his pack to reveal its light shining in the darkness, it also revealed him.

"What the light reveals, however, is not Earendil or Beren. Rather it is "Frodo, hobbit of the Shire," hardly a heroic epithet to match Beren One-Hand or even Earendil the Mariner. Yet it is not mockery. For they are all part of the same tale..."

Hillman brings a bit of Tolkien's analysis of The Battle of Maldon, an Old English poem -- perhaps the last one composed before the Norman Conquest. Sam is like these Anglo-Saxon men, defeated at the battle and yet different too.

"As Hammond and Scull have noted, the hardening of Sam's will as he wearies beneath the burden of the Ring is a clear echo of the famous lines in the Old English poem, The Battle of Maldon, lines which Tolkien rendered as "Will shall be the sterner, heart the bolder, spirit the greater, as our strength lessens."

"Love of his master and plain hobbit sense allow his humility and his reason to shrink the hero back down to a terrified halfling gardener. Thus, unlike Beorhtnoth whom ofermod moved to make a grand and foolish choice, Sam, can in this moment see through the lies of glory and renewal grown from his fantasies by the power of the Ring. He rejects the choice of Beorhtnoth as he had previously done that of Beorhtnoth's heorpwerod."

I could put a dozen more quotes in here. Tolkien was a master of figuring out after the fact what his work actually meant and his letters and other writings are able to be mined.

It seems that Tolkien realized that Frodo failed in his quest and this failure, along with the loss of the Ring, left him a shell of himself. Anyone with greater power would never have gotten so far along the path without claiming the Ring for himself, but on the other hand, only Bombadil would have had such a lack of desire for the Ring in order to attempt its destruction.

I hesitate to know whether to recommend this book. It is a scholarly book that draws on many sources. Maybe it helps the reader to understand some of the themes better of this wonderful work, but maybe, through deep analysis, it steals some of the joy of the story.

Gandalf told Saruman that "He who breaks something to find out what it is, has left the path of wisdom." This is true and at the same time, if we understand how Pity and the Ring's Power play across this great story, we will understand the beauty of what Tolkien created here.

[John · Rating 4 out of 5]

I heard Tom Hillman talk about his love of Tolkien's legendarium on the Prancing Pony Podcast (see my review of the hosts' Why We Love Middle Earth book) while I was already reading this. I had to get it from my public library ILL as it's not easy to come across on open shelves and it took a while to get through at about a chapter a sitting. As a retired classicist, Hillman brings his expertise in close study of etymology; determined attention to the primary sources of letters, essays and edits; academic investigation; and an appreciation for the pagan and the Christian contexts which blend, as in the Beowulf-poet, in LoTR. I like that Hillman's not reductively looking at LotR as religious per se, and he respects Tolkien's diligent efforts to elevate ethical questions of Pity and Mercy into capitalized and moral functions without taking the "easy" out of matching the Primary to the Secondary World. Hillman sustains a tenaciously held grip on his titular main three nouns.

Although of course The Hobbit, the Silmarillion, and bits of HoMe also feature, it's the core text that Hillman concentrates his extensive study upon, and I'm surprised how doggedly he can stick to the argument of the whole while dissecting particular phrases and words at great length. It's a skill to do so in an accessible manner respecting the professionals who now (as opposed to when I first found Middle-earth in fifth grade in 1971) dominate the field, while enabling those like me to follow along, playing catch-up over half a century later with what's been learned about Tolkien's creation.

I'm listing key quotes for the convenience of those wanting a glimpse of the diligence Hillman and Tolkien share. Previous GR reviewers haven't cited from its actual pages, so I do so to enrich the discussion of a volume that deserves to be better known and more widely available for research.

About Letter 142 to Fr Robert Murray, SJ, when religion is "fundamentally" but not obviously present in LotR revision, Hillman reflects that the Ring's better seen as if like gravity rather than addiction (34-5.) Much later, Hillman suggests the analogy with gravity in space, even if the object is no longer under the force, the mark's still left upon the object formerly warped as in Frodo's case.

Lacking Bilbo's encounter up close and personal with Gollum, Frodo early on can't commiserate with the creature's suffering; he must do so without a "leap of faith" into the dark as he chooses his mission (71-4). This next possessor of the Ring approaches an "acceptance of death" (77). Frodo wills to take the Ring, while Gollum took it out of necessity under the circumstances of its lure (121).

Hillman continues: "Gollum's initial retreat on Mount Doom is a tactic of Frodo's final threat there a failure. Enslavement by the Ring trumps service in fear" (149). "Where love's roots are deep, it may stay the hand of a Frodo; where its roots are not deep, Smeagol may speak love but use none" (168-9). Although this point needed elaboration--given as he notes as an aside it's influenced the Jackson films--Hillman rejects the view that the Ring is a "conscious entity wielding an agency of its own," but "[i]t is rather the power of the Ring with which we tempt ourselves" (200). The "we" is telling as Hillman opens up its sway to include all who gaze upon it with desire; I thought in wry passing of the folly, to me, of marketing it as an icon in fandom today as a bauble; I'd regard it as a potent talisman with the danger of a certain crooked cross or hex, to say the least, not as gimcrack.

Hillman notes how "the self-deceptions of Ringbearers about the Ring do not cease simply because they no longer possess it" (212). LotR fuses immortal perspectives with mortal limitations similar to the Beowulf-poet's heathen-Christian blend of motivation, narrative, and mindset (238). He refers to Glen Robert Gill on biblical archetypes in Paul Kerry and Sandra Meisel's 2011 anthology in using Northrop Frye's "analogy of revelation" to resolve the paradox Tom Shippey in "Author of the Century" (on its pp 210/ 223) raises to account for how Tolkien can apply non-Christian primordial frameworks to invigorate his story; I find this a refreshing counterpart to a now-prevalent equation of the legendarium with the Good Book and Sacraments which certain critics calculate as if the only solution to Shippey's problem (241). Hillman reflects: "Perhaps we confuse the parallel trajectory of an imaginary world, a Secondary World in mythical time, for what many, including Tolkien, believe to be the trajectory of the Primary World" (263). He resists the facile pagan vs. Christian dichotomy.

Instead, Hillman insists upon finding eucatastrophe where the levels of Grace and of Nature meet, where despite tragedy, fairy-stories embody that truth of a happy conclusion after pain, grief, and mortality. This critique can be dense in explication although never descending into jargon, self-congratulatory score-settling, or snide asides; the endnotes deserve careful examination as he clarifies differences with what others have observed. While not for beginners to Tolkien's texts, it's a rewarding immersion that I, despite not having the familiarity with the corpus beyond the central books, could emerge from with a respect for such extended concentration upon this central theme.

[Henry Pensell · Rating 4 out of 5]

One interested in this book should have read The Lord of the Rings. Having read The Hobbit and The Silmarillion will make getting through Hillman’s work easier and more informative but is not necessary. Hillman’s close reading of the Lord of the Rings trilogy takes the reader through each segment of the story of the Ring with careful attention paid to the ideas of pity and power, but also to “all the themes–of Death and Immortality, Fate and Free Will, Power and War, the Noble and the Humble, Love and Home, Justice and Mercy” (267). Through this lens Hillman analyzes the true nature of the one Ring and its bearers along with those who refused the burden. Someone with a strong interest in the subject and desire to do further reading will gain the most out of this book. Hillman references many works by both Tolkien and scholars; the astute student will find many jumping off points from which to explore. I came into the experience without having finished The Silmarillion but still gained valuable insight to the Legendarium. Hillman draws connections throughout his reading that I had never considered before but left me with lots to think about. For instance, in chapter nine Hillman compares Bombadil to Shelob, “both Bombadil and Shelob are their own masters, one wholly good, one wholly evil. Neither is interested in dominating the wills of others.” (175) By reading along with someone so well-learned in the subject as Hillman, everyone stands to glean something of value. Hillman will analyze a passage of text by considering the different ways it appeared in various drafts and the timeline of when Tolkien wrote specific lines. He truly did an incredible amount of legwork in organizing outside information for us to reap the benefits. Hillman writes “Frodo’s denial of pity proceeds from his conviction that Gollum deserves death, not pity” (74). Today it can be so hard for us to find pity in ourselves, especially for those who we believe (perhaps rightly) do not deserve it, like Frodo with Gollum. Reading Hillman’s work helps us to consider the when, why, and how to find pity (and Pity) in our lives.

[Maggie Lin · Rating 4 out of 5]

Tom Hillman’s Pity, Power, and Tolkien’s Ring is a deep-dive analysis into the inner workings of Tolkien’s major literary themes in The Lord of the Rings. Hillman walks you through every aspect of the series including: character philosophies, Middle-Earth’s world-building, Tolkien’s writing inspirations and process, and much more. If you are a dedicated fan or scholar of The Lord of the Rings and would like to know more about Tolkien’s narrative development, then this book may be a great read. At its core, this book focuses on the role of pity and how it is an important component to overcoming the evil befalling Middle-Earth. While this theme is very obvious in Tolkien’s original work, Hillman’s expert analysis allows to reader to better reflect on the choices of pacifist characters such as Frodo, Tom Bombadil, and Bilbo against their foils as well as consider the power of pity in the realm of reality. In many ways, it inspires me to take up The Silmarillion to delve back into Tolkien’s world and characters. Hillman also infuses his writing with clever humor, keeping what would be a dense read lighthearted. Comments such as “one does not simply walk out of Mordor” balance out the profound stretches of narrative exploration.

[Joshua · Rating 5 out of 5]

A thoughtful and deep dive into the main themes of not only The Lord of the Rings, but J.R.R. Tolkien's entire legendarium. Hillman not only does a razor close reading of the text, but brings in Classical, linguistic, and religious background to give some wonderful insights about Frodo, Bilbo, Gollum, and the Ring. Hillman also connects with other Tolkien scholars and lovers, bringing as many voices as possible into his discussion.

The highest compliment I can give a book about Tolkien is that it made me want to immediately start rereading all the books, and 'Pity, Power, and Tolkien's Ring' gave me that feeling from the first chapter.

[Susan Ferguson · Rating 5 out of 5]

This presents many different ideas about the power and effect of the ring. Many ideas were new to me. I had never considered things in this light. Good research among Tolkien’s papers and letters. Very interesting and insightful.

[Sørina · Rating 5 out of 5]

Here's my review: https://digitalcommons.georgefox.edu/....

[Kim · Rating 5 out of 5]

Tom is amazing in the way he gets the reader to think more deeply about Tolkien, the LotR, and the entire legendarium. Read this book.

[Martina]

My review is available here: https://brill.com/view/journals/rart/...

[Renada Thompson · Rating 4 out of 5]

Powerful and unsettling to many of my well-worn and comfortable readings of characters and events in LotR. Highly recommend and will reread.

[Jacob DeBoer]

An excellent study of some of the themes most central to Tolkien's magnum opus.