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The Deaths of Sybil Bolton: Oil, Greed, and Murder on the Osage Reservation

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For those seeking a true family story of the Osage Reign of Terror portrayed in Killers of the Flower Moon

Journalist Dennis McAuliffe Jr. grew up believing that his Osage Indian grandmother, Sybil Bolton, had died an early death in 1925 from kidney disease. It was only by chance that he learned the real cause was a gunshot wound, and that her murder may well have been engineered by his own grandfather.

As McAuliffe peeled away layers of suppressed history, he learned that Sybil was a victim of the systematic killing spree in the 1920s—when white men descended upon the oil-rich Osage reservation to court, marry, and murder Native women to gain control of their money.

The Deaths of Sybil Bolton is part murder mystery, part family memoir, and part spiritual journey. 

350 pages, Paperback

First published August 23, 1994

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Dennis McAuliffe Jr.

2 books11 followers

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5 stars
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84 (21%)
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33 (8%)
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Displaying 1 - 30 of 57 reviews
Profile Image for Claudia.
2,664 reviews116 followers
August 21, 2017
I feel a bit duped...I bought and read this book thinking it would add to my understanding of the Osage Reign of Terror in the 1920's...Sybil was an Osage, one of those rich Natives that the whites in OK seemed to hate...

But the author did an about turn in his book, and in the intentions of his original project...

McAullife learned that his maternal grandmother was an Osage who died of kidney disease, or was it suicide? Or, was her death at 21 part of the murders that plagued Pawhuska.

He works hard in the book to incorporate his new knowledge of his Native heritage (hard to get a handle on the strength of his DNA connections), and his drive (at first) to prove his hateful grandfather to be a murderer.

So, he travels to Pawhuska, intending to interview, to read and research, to write. Instead, he interviewed, read and researched, and drank. He drank a lot.

He and his father built a credible theory of Sybil's murder...NOT targeting Sybil's estranged husband...but then he falls apart...totally.

I learned through his research -- more exhaustive than in KILLERS OF THE FLOWER MOON, and that is what I came to the book to learn. That, and an investigation of Sybil Bolton as a person.

Instead I got a 'Lost Weekend' memoir...and, most troubling at all (it was hard to finish the book, actually), blaming his Native heritage for his drunkenness...it's all in his genes. I politely say, "BS". I'm not sure what the research into racial sensitivity to alcohol, but it's clear now. There is a family link, but McAuliffe's mother, father, maternal grandfather...none had a weakness. And Sybil? She didn't live long enough for us to know.

I left the book uncomfortable...an itch between my shoulder blades...Sybil Bolton was NOT served well in her grandson's book, IMHO.
Profile Image for Joan.
551 reviews28 followers
March 30, 2023
Everyone should read this book. It is non-fiction. The author is (or was when he wrote the book in 1994) an editor at the Washington Post. The book was republished in 2021 with a forward by David Grann, author of the very much related Killers of the Flower Moon.

The book is about a discovery the author made about his own family history. When his mother became very ill and thought she might be dying (she recovered) she called Dennis to her bedside to tell him the woman he had known all his life as his grandmother (her mother) was her step mother, the 2nd wife. She went on to tell him her birth mother died not long after she gave birth to Dennis' mother. She had died of kidney failure related to the difficult birthing process or so the story went. But that wasn't the most shocking part of the news...his grandmother was a "squaw." And this meant he and his mother were "half-breeds." [Obviously this all took place prior to the current fascination with many people claiming Native American ancestry and looking favorably upon the "exotic" heritage. Back then this was considered a "stigma."]

Being a researcher Dennis is fascinated and wants to learn the details and uncovers quite a story about Sybil Bolton and her Osage heritage and all that this entails. She even had a tribe number #933. Anyone who has read David Grann's Killers of the Flower Moon will get some hint as to where this is all heading.

This is a MUST READ for anyone who has ever done any research into Native American genealogy. My only quibble at all with the author is when he briefly strays off course relating his own research and Sybil's story and proceeds to tell us about famous people with Native American ancestry...only from my own research I know most of those stories are myths...he shouldn't have opened that can of worms. But I can forgive this all too common lapse given the valuable information included in this story -- the facts sometimes fly so fast your head will spin.

I only wish the book had included photos of the family members that are written about here. The author does a great job of describing them...but photos would have really brought them to life.
17 reviews
December 7, 2017
I would have given this book one star, if it did not contain all the history of the Osage and their reign of terror. But, throughout most of the book Mr. McAuliffe seemed to whine about his problems.
Profile Image for Smalltown.
248 reviews1 follower
July 17, 2017
Read as follow up to another book about the Osage. Some interesting information here but was more about author exorcizing his personal demons. A bit whiny, rather pretentious.
Profile Image for Lori Bigler.
56 reviews
August 4, 2023
Was a bit disappointed for several reasons. First, I wasn’t that interested in learning that the author mostly considers himself an Osage because he has an obvious drinking problem. Second, more than once, the author went off on a rant. One of them was about the “Little House” books, saying they were basically trash that no child should ever read. I can think of a lot more disingenuous books that portray the Osage tribe more negatively. The POV of the Wilder books are of a child, an uneducated child from a different generation and time. In no way am I saying the portrayal is admirable, but all books need to be considered 1) in the time in which they were written. 2) the time in which they are set, and 3) the time in which they are read. I did not see how going after “Pa Ingalls” as a “creep” helped tells the authors story. Third, the author also has a crass view of any area not like the one in which he was raised. The area south of Pawhuska and Pawhuska itself is a beautiful area of rolling hills, thick foliage, and rugged terrain. Though obviously partly said in sarcasm, the author’s cutting descriptions of the people and the place did not give an accurate description or portrayal of the area. This book is not on the level of “Killers of Summer Moon”, and at times just seems like the author is capitalizing on his ancestry that he only recently (in relation to his writing) discovered. This review is the first I remember writing that takes the author to task, but honestly, I just didn’t feel giving the usual positive review would be honest.
Profile Image for Brian.
105 reviews19 followers
March 13, 2021
The story of McAuliffe's journey to discover the truth about his grandmother and other Osage people from the 1920s is incredible. This is a powerful book that demonstrates resilience.

My concerns are few. As someone who already knows a lot about Native American and Oklahoma history, I felt the book was a bit slow. He goes off on tangents--some of which are useful, some are funny, and others just slow down the story. He also uses some language regarding Native Americans which was more accepted when he wrote the book, but in 2021 it has not aged well and comes across as racist. For example, he connects his own alcoholism with his discovery of is "Indian" identity.

Overall, for someone who has never heard of the Osage Rein of Terror and knows nothing of Oklahoma history, this is a great book.
Profile Image for Koontzs.
29 reviews4 followers
April 15, 2019
Personally I liked McAuliffe's prior book about the same subject. It was titled, "Bloodland". They are both about the Osage Murders that took place in the early years of Oklahoma statehood. McAuliffe's mother was a victim, despite being reported as a suicide at the time. Many tragic deaths happened, all because of the greed of white men, looking for the easy money of Osage Indian headrights.
33 reviews
April 19, 2021
Wow! Anyone from Oklahoma needs to read this book. It is very thoroughly researched and well written. So much of the true Oklahoma history was never taught in our Oklahoma schools. It is disturbing what was done to the Osage Indians. SO much corruption and heartache.
Profile Image for Minna.
130 reviews23 followers
April 14, 2021

A polite conversation with a ninety year old in a barber shop reveals a shocking family secret that sends a grandson on a journey of discovery and self destruction. This murder mystery approaches the Osage Reign of Terror from a personal angle. It restores a murder victim’s place of honor among her family and brings them home to their Osage heritage.
Profile Image for Mel.
94 reviews
July 31, 2024
This was a challenging book to get through. The road was long and windy and I ended up learning or challenging my own perceptions of many things. But I did not learn much about Sybil Bolton. Here's some thoughts broken down vaguely in order of how they occurred in the book.

The Foreword
I was honestly bummed that the person writing the foreword was not Osage but David Grann of "Killers of the Flower Moon" fame. Having a white guy who spent a year following one family's tragedy and then making it big off that tragedy lending his name to establish credibility of a man who used his discovery of being Osage himself in order to try and discover what happened to his grandmother is grating. Having David Grann talk about his own book and then events that took place in his book, not having to do with Sybil Bolton except peripherally for half the foreword, was almost offensive. There was no personal connection to the author or any comment on how his story moved him or inspired him to start his own journey 20 years later with the murders of Osage people. It was a distanced and impersonal five paragraphs.

The Good and the Not So Good
The story itself was sometimes a long rambling stroll from fact, to fiction, to imagination, to indignation, to rants about unrelated topics often without page breaks between paragraphs to let the reader know that we were boarding a bus to a new topic. Several times within a span of three paragraphs I would have to go back and be like...oh we're no longer in the present but an imagining of 1925??? Sometimes within a single section we would go from the present, to the past, to a rant on the "Little House" books to the present, to historical facts about the Osage in the same time period as the "Little House" books, back to the present and it was honestly hard to keep up with a semi-stream of consciousness reading of it all.

I will say though that I learned many things along the way on this journey that I did feel grateful for. One involved the rant about "Little House on the Prairie". I never really gave the books much thought as an adult, but having McAuliffe recontextualize the history of what was actually happening during the books was eye opening. I never knew that the Ingall's were illegally squatting on Osage land, that they built their house, as around 500 other families did at this time on the reservation. He found records of their family not filing a claim since their homestead was listed on Osage land. These settlers would form vigilante groups and incite violence and get the army involved which only benefited white people. McAuliffe makes a point to draw the readers attention to the fact that these books remain wildly popular with children and parents despite anti-Indian slurs, and the painting of Native Americans as barbarians; for other ethnic groups we no longer tolerate such heavy handed racism and yet we all look back on the "Little House" books with nostalgia. Him also bringing up the, "why couldn't Pa hold down a job/homestead" was funny but also like, WHY couldn't he? Why did he leave the family and comfort of a community in Wisconsin to drag his family all around stolen land? Also an interesting tidbit I didn't know is that these books were promoted by the government for showing "positive representations of America" after WWII. I have a new interest in reading these books again through the lens of "the American Spirit" propaganda.

McAuliffe did not hold back any of his hard feelings about his ancestor's treatment, whether by local white people, the Oklahoma courts, the federal government or the FBI. He also did not censor the toll this journey took on him - his spiral into alcoholism as he was researching his grandmother, and his multiple relapses while trying to write the book.

On the flip side, he also did not seem to care about slipping his own racial slur against Black people into this book after railing on about how he didn't like anti-Native slurs to be used against Native Americans. He wondered if his drinking and relationship problems were because he was Osage and used these stereotypes instead of pointing to his white Irish-Catholic background to explain these things instead. He also commented he came to Osage county looking for Indians, but only found white people - despite the fact that anyone looking at him would see a white man with sandy hair, blue eyes and pale skin. All of this showed a stunning lack of self awareness, and a stunning lack of growth on behalf of the author to recontextualize everything he was coming across and learn something.

Despite learning much about the racism behind blood quantums, popular fiction, The Washington Post, the author himself - we don't learn much more than we knew in the first third about Sybil Bolton and her death. The author throws the same conspiracies against the wall throughout the book with no evidence but historical probabilities and hearsay, hoping something will stick and nothing ever does. McAuliffe ends the book contented with the fact that he's gained a place in his tribe, and that he doesn't need to know the specifics of what happened to his 21 year old grandmother. Much like this book was eye opening along the way unexpectedly, so too the author found the journey more important it seems.
Profile Image for Taylor G.
327 reviews
January 27, 2025
3.75/5

A decent companion book to 'Killers of the Flower from a different perspective. The beginning was much more interesting as you see how the author decides to investigate his family tree. But the end was a condensed version of 'Killers' and the investigation falls off...
6 reviews2 followers
July 7, 2022
After listening to Killers of the Flower Moon I thought this would be a good follow-up and it was highly recommended to me from knowledgeable folks during my visit to Pawhuska. Wow, what an incredible disappointment. This turned out to be nothing more than the angry, hate-filled, and even racist ramblings of a self-proclaimed alcoholic who couldn't seem to find enough people to hate, including himself. After intricately describing how it angered him that people did not think him to be of Native American ancestry because of his pale skin and red hair, he proceeds to judge everyone throughout the book by how they look and even states that before his trip to Pawhuska he had never seen a "real Indian." But he did have to suffer through the "hillbillies" of Southern Missouri to get to Oklahoma. These are people who eat his ancestors by eating the fish of Truman Lake and Lake of the Ozarks. Even Shoji Tabuchi was not safe from his prejudicial anger stating that the "hillbillies" only like his music because he is Asian. As for the derogatory reference about the farmer that raised collard greens? Well, that was just par for this course. It's unfortunate he blew the opportunity to really delve into the death of Sybil Bolton opting for narcissistic ramblings of how his life sucks. Yes, it does suck to live as a rage filled hater, but that is your decision. There are sections that exhibit his skills as a good journalist but they just too far apart. Myself and my two co-readers began referring to him as "angry boy" because he can't seem to find anything that doesn't spark his anger. If there isn't something to be angry at he will extrapolate on a totally unfounded speculation and become angry at that. The intended topic of the book deserves so much better and what makes it so sad is that Sybil was his grandmother but he would not curtail his range and hate to let her story have the telling it deserved. Skip this one be sure to read Killers of the Flower Moon or read Killers again.
Profile Image for Cynthia.
Author 4 books776 followers
January 26, 2022
This was fascinating. I discovered this book because it was mentioned in David Grann's Killers of the Flower Moon. While I found Flower Moon to be a good read, too, what I loved the most about The Deaths of Sybil Bolton was how much heart is in this story. It's simultaneously a deeply personal family story and a thorough investigation of a shameful period in this country's history. I learned so much, and for weeks and months afterward, I could not stop thinking about Sybil and her family. Highly recommended.
Profile Image for J.J..
2,691 reviews22 followers
February 4, 2022
This is a deeply personal history the author has brought to the public. It’s not as compelling as Grann’s Killers of the Flower Moon but has a hidden family history element that makes it equally as important to the study of the Osage. And it posits questions about who is and Osage, what makes them Osage and how to we best carry a difficult past into the future and in the open. Historians, genealogists, true crime and mystery readers will all enjoy.
Profile Image for Kelsey Bodenhamer.
61 reviews
January 28, 2023
Wonderful personalized vision of historical tragedy

I read Killers of the Flower Moon and was sorely disappointed. What I was seeking was knowledge about a rich native heritage and a clearer account of the historical events surrounding the Osage murders in the early 20th century. I found what I wanted in this amazing book. The author had a personal vested interest and it shows in every page. This is the book about which a movie should be made.
2 reviews1 follower
April 18, 2008
Interesting history of the author's family. He is Osage Indian on his mother's side, but this had always been a family secret, as was the cause of his grandmother's death. It was of particular interest to me as I have a minor in Minority Studies with an emphasis on the American Indian. This book also recalled to me the many injustices that native americans have suffered.
12 reviews1 follower
October 29, 2012
One of the most memorable books I've ever read. I read it many years ago, would probably have given it 4 stars then. But any book that I recall and still influences me 15-20 years later gets an extra star! It's no longer in print, but if you ever see it, read it. It will add a new perspective to US:American Indian relations.
Profile Image for Shannon Smith.
1 review4 followers
May 31, 2015
Fantastic investigative journalism into a horrible conspiracy. Through very small clues, McAuliffe figures out a very clear picture of what actually happened to his grandmother, instead of her reported kidney/suicide death his family had heard about their whole lives. It's also a great reminder of how taboo being Native American is, even in very recent times.
Profile Image for Koontzs.
29 reviews4 followers
November 11, 2017
Local history. May not be for everyone, as it has a lot of detail and side stories. Not a quick easy light read. BUT living next to Osage county, it is amazing that such discrimination and murder was rampant there so recently (am I showing my age?) This is a good companion book to the popular "Killers of the Flower Moon" by David Grann.
Profile Image for Shannon.
522 reviews6 followers
January 8, 2014
I did not care much for this biography. I know everything in it was tied together, but it just seemed to not flow very well.
Profile Image for Robert.
1,342 reviews3 followers
June 4, 2023
This is a good companion to Killers of the Flower Moon. McAuliffe dives into the Osage Reign of Terror period from a more personal angle than Grann, digging up family stories to better understand the death of his grandmother. It gets muddy and nasty. The book rather beats to a pulp some of the machinations of everyone from the US government down to the town businesses and personalities, mostly whites. Many passages of this book inspired, or were lifted by Grann for his book, though some events get a slightly different retelling in his work.
Again, despite the time period, the Tulsa riots receive not mention, though the contribution of white prejudice against blacks certainly provided background for events in the Osage nation.
Wonder if these two books have already been banned in Texas, if not in Oklahoma.
Profile Image for Jane Gardner.
356 reviews
November 14, 2023
This is a powerful story of the discovery and history of the Osage executions of the original people and their rights to the land that was oil rich. Reading this story made me ashamed to call myself a white American. The tragedy of this whole period was the elimination of the Osages with headrights
to this land awarded them after driving them off their original lands in Missouri. Due to the greed of the white men who acted as Guardians of the tribal members who held the mineral rights to an oil rich land of several hundred acres each based on the rights awarded to them by the government in removing them from their own lands. It is a well written account of a truly terrible time and an extermination of people who did not deserve the fate they received. I think it should be required reading for all Americans.
208 reviews
June 30, 2024
What began as a Washington Post journalist's curiosity about how, exactly, his grandmother had died became an all-absorbing quest to track the violent deaths of many Osage Indians in 1920s Oklahoma, and why they were targeted. His commitment to pursue this story's leads and his unflinching honesty lead him to a shocking, searingly painful family history that was hidden for decades.

I read this book almost exactly 20 years ago and remember parts of it quite vividly. I have recommended it dozens of times and very highly recommend it to anyone who believes, as I do, that this history should never be forgotten.

Despite my 5-star rating, I do have a caveat: the writing tends to wander between clear-headed journalistic style and some long, almost unhinged rants. If you can look past the writing style and get into the story, the journey is worth the effort.
Profile Image for Chiara Ferrari.
826 reviews5 followers
March 13, 2024
A disappointing look at a tragic and fascinating period. Reading the history of Native American - European-American relationships (among other things), I have given up the idea that there is any bottom to the depths of human depravity.
Unfortunately, this is a book that I opened with great anticipation but the story is more about the authors life and battle with alcoholism and very little high-level coverage on the history of Osage. The discussion on Sybil Bolton’s death is more of the author’s conjecture and emotions wishes, which are not supported by his findings.

For an extremely powerful book on this subject, I recommend David Grann's Killers of the Flower Moon: The Osage Murders and the Birth of the FBI .
Profile Image for Susie.
445 reviews
July 9, 2024
I went back and forth about this book. Parts of it I really enjoyed, and parts were a struggle to get through. Overall, I liked learning more about the history of the Osage, though it was painful to read how many ways the United States has failed the Native nations who well-preceded us as inhabitants on this land. I thought the author provided a lot of good insight, yet he also used terms toward other ethnic groups that are definitely not acceptable by today's standards (this was published thirty years ago). I wish that more of these events were taught in basic American history classes. I hope that we are moving in that direction.
Profile Image for Marianne.
83 reviews1 follower
July 25, 2023
I first tried to read this a couple years back on the heels of reading Killers of the Flower Moon, as the obvious follow up, but couldn’t get into it. I think I was mentally too tired to keep up with more names and characters. Picking it back up, this time I couldn’t put the book down.
It is a personal and emotional journey of the author’s discovery of his Osage heritage as he delves into the circumstances surrounding his mother becoming an orphan as a baby during the Reign of Terror in the 1920’s that Killers of the Flower Moon so meticulously details.
Profile Image for Marilyn Brown.
198 reviews7 followers
November 19, 2023
3.5 overall, I enjoyed the book. However, it had a little bit too much of the author’s personal information (not a fan of blaming his race for his alcoholism). As an investigative reporter, I was more interested in learning the facts of her death. A lot of his answers were supposition. That period of time was never taught in Oklahoma history and I did find myself delving into emotions and thoughts I had growing up based on the limited information I had.
9 reviews
February 14, 2024
This is a very serious subject. Unfortunately, the author wasn't sure if he was an historian or a comedian. The history of the Osage needs quite a bit more gravitas and less "all about me the author."
The final bit about his time in rehab is simply irrelevant to the subject. And we still do not know what happened to Sybil. I want my money back! I cannot believe the writer is a journalist for the Washington Post.
Profile Image for Robyn Swenson.
29 reviews1 follower
January 31, 2023
This is the second book that I have read about the Reign of Terror for the Osage people. It’s a little known time of tragedy and the author does well in describing the factors that led up to it and exacerbated it. It’s, frankly, disgusting. We all need to know about these events.
However, the digressions into the author’s personal life did not add to the quality of the book, in my opinion.
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