Old Murder & Modern Love: Lessons Learned from the Original Cool Girl

On July 11, 1906, a woman by the name of Grace Brown took her last breath. People have not stopped speaking of it since. 110 years later, this sensational story of betrayal and murder reveals a great deal more than you might expect about men, women and modern love.    

…”I wish for your sake things were different, but I have done all I can to prevent you being bothered.”  
Grace Brown in a letter to Chester Gillette, July 1906

I could not stop thinking about Grace Brown. You may have heard of her…or not. I didn’t know her name until I picked up a book in a local shop. I had kind of, sort of heard her story before. I didn’t know many details. At best, I had a foggy recollection of a long-ago tale of mystery and murder. I knew it happened somewhere in Upstate New York–not far from the various places I have called home. I knew the story had captivated people–making its way into a classic novel, a famous movie and even an opera.

What I did not know is that Grace’s story and, more specifically, her own words would speak to me, even haunt me, in ways a modern woman would not have thought possible.

Meeting Grace Brown

I love books–actual books. I don’t own a Nook or a Kindle. And while I do indulge in the occasional audiobook, I still like turning pages and I don’t mind the extra space a good book takes up in my bag when I go on vacation.

I also love places that sell books. One place, simply called “The Book House,” is one of my favorites. With its tidy wooden shelves stacked with carefully-chosen collections, it feels more like the private library of a particularly interesting friend rather than a store. Somehow this place manages to survive in the age of cavernous corporate booksellers and digital everything. It is small, peaceful and quiet–a welcome lair for people who still enjoy courting the danger of a paper cut.

It was in The Book House that I first became acquainted with Grace Brown by way of a substantial paperback in the “local interest” section. Murder in the Adirondacks: An American Tragedy Revisited was a new and improved version of author Craig Brandon’s bestseller.

“Oh, this story…” I thought to myself as I picked up the book, reflexively flipping it over to find a blood-red headline announcing “Trial of the Century” on the back cover. Beneath that, and carefully placed within the summary, were two black and white photographs.

The top photograph was a crisp portrait of a dashing young man with the slightest hint of a smirk. The other was a somewhat muddied print of a young woman, her face partially obscured by what appeared to be an ink smudge. The unflattering defect gave the vaguest suggestion of a five o’clock shadow yet somehow managed to highlight the woman’s eyes–locking any beholder into their eerie stare. There was a sense that it took great effort for the woman to focus on the camera lens, her gaze betraying a mind a million miles away.

This first introduction to Grace Brown and Chester Gillette tells you much of what you need to know about them–both individually and as a couple. Still, I reasoned, there must be a great deal more to the story. I decided to buy the book and delve into what I figured would amount to little more than an early 20th century Dateline episode–a perfect summer read.

I had no idea.

Grace and Chester

In simplest terms, the story of Chester Gillette and Grace Brown is this: a well-traveled city slicker/bad boy and a simple, country girl/farmer’s daughter meet at work. One thing leads to another, she gets pregnant and hopes for marriage…but he’s …just not that into her. There is concern–even panic–on Grace’s part. This was, after all, the early 1900s and there were very few options for unwed mothers. Chester, meanwhile, tried to employ the classic maneuver of ignoring the problem in hopes, perhaps, it might just go away.

It did not.

Ultimately, their affair ends in a rowboat on a lake in the Adirondacks. No one knows exactly what happened on that July day more than 100 years ago. What we do know is that while Chester and Grace headed out together, they did not return the same way.

Days later, Chester was miles from the lake–visiting friends and taking snapshots–while Grace’s body was found floating beneath its surface. She had apparently suffered at least one blow to the head.

Grace Brown was 20 years old. She was in love. She was pregnant. She was desperate. What may be most shocking, though, is that up until the moment of her death, Grace Brown was trying to be “cool.”

The Cool Girl

“Cool Girls never get angry; they only smile in a chagrined, loving manner and let their men do whatever they want. Go ahead, shit on me, I don’t mind, I’m the Cool Girl.”  
Gillian Flynn, Gone Girl 

“Oh my God.”

That about sums up my reaction the first time I read the “Cool Girl” passage in Gillian Flynn’s Gone Girl. The phrase crossed my mind twice, actually. The first time in astonishment at its accuracy, the second time in disgust at myself for having to admit to, on more than one occasion, trying to be that person.

And the Cool Girls are even more pathetic: They’re not even pretending to be the woman they want to be, they’re pretending to be the woman a man wants them to be.” 

“Oh my God.”


I had the same reaction when I began to read Grace Brown’s letters to Chester Gillette.

Grace Goes Home

After discovering she was pregnant, and with some urging from Chester, Grace decided to move from Cortland, N.Y., where she had been living and working, back to her parents’ home in South Otselic. The plan was that she would stay a few weeks, sew some new clothes and then Chester would come for her and the two of them would run away to the Adirondacks. The purpose of the trip, however, was unclear. Grace, of course, hoped they would marry and begin a life together. Chester would later testify marriage had been considered but no promises made.

Given her “delicate condition,” not being found out was of the utmost importance. Despite moving home, Grace (or “Billy” as she was affectionately known) didn’t tell her family about the baby. This was a young woman who, by all accounts, throughout her life, had shared everything with them. It’s believed she really didn’t reveal her secret to anyone–which left Chester as her only confidant.

From practically the moment they are separated, Grace begins sending letters to Chester. She shares that she is miserable, frightened and lonely. She asks him to come for her as soon as he can and pleads with him to respond to her letters.

Initially, Grace receives nothing from Chester, but she continues to write.

In one letter, she mentions a correspondence received from a female acquaintance in Cortland. According to Grace, the woman reported that Chester was “having an awfully good time” and had even been seen in the company of another woman. Chester would later deny the reports and ultimately, Grace elected to dismiss them…at least to Chester. She instead pledged her faith and loyalty, even going as far as to say that if she dies, she hopes he can be happy and do as he likes–acknowledging the “trouble” she’s caused him.

You can almost feel her words trembling on the page. In the end, though, Grace Brown just tries to be upbeat and play it cool.

Grace’s Letters

Grace sends one letter and then another and another–she begs, she pleads, she continues to tells Chester she needs him. She continues to receive no response–all the while fending off sickness and the growing insistence by her family that she see the local doctor–a suggestion she, of course, rejects.

If things were bad for Grace Brown, it seems they were only getting worse.

Like a modern lady with a string of unanswered text messages, though, Grace is hopeful. She begins to worry that, surely, Chester is sending her letters but there’s just been some sort of problem, a mix-up and they aren’t getting through.

June 23, 1906

My dear Chester–I am wild because I don’t get a letter from you. If you wrote me Tuesday night and posted it Wednesday there isn’t any reason why I shouldn’t get it. Are you sure you addressed the letter right?


It seems an impossible situation but what is even more remarkable is that Grace–with no leverage or support and everything to lose–pleads with Chester to not find all of her worries and requests unreasonable. She never asks for his attention without also asking for his forgiveness. She is more concerned with making him happy and ensuring he is “not cross” and “having a good time.” One may presume that she hoped her accommodating attitude would win his heart.

She’s The Cool Girl.

You Always Know

We have all been here, haven’t we? Unrequited love? It’s a pretty-sounding pair of words for something that knocks the wind clear out of your chest and shreds your heart into useless scraps, stopping only to knee you square in the face.

The worst part is–you always know. No one ever wants to admit it, but you always know. Grace knew Chester was getting her letters like you know your boyfriend or girlfriend–the one with the cellphone constantly implanted into one hand or the other–absolutely, 100% got your text message and is just…not…responding.

The funny thing about love, unrequited or otherwise, is that it makes you want to believe the best in people–even when every action flies in direct conflict with that belief.

“Dear, Grace…”

Finally, after several days, Chester responds. Not long after you begin to read his words, you can quickly imagine Grace’s heart sinking as she did the same. His first letter is a disappointment in length, tone and information. Most notably, he downplays her concern, even expressing surprise at it, writing:

“Don’t worry so much and think less about how you feel and have a good time.”

He is casual. He tells her there is no reason to worry while adding that he cannot come for her early as she has requested. It was, very likely, the very last thing Grace Brown would have wanted to read.

To her credit, though, she lets him know. The letter she sends next can, in many ways, be summed up with just three words.

“Oh. Hell. No.”

Grace fires off a response putting Chester squarely in his place, something he has surely had coming. Line after furiously-written line she, pardon the expression, calls him out on his bullshit.

“I do not see why I shouldn’t be discouraged,” she writes. “What words have I received from you since I came home to encourage me? You tell me not to worry and how I feel and think less about how I feel, and have a good time. Don’t you think if you were me you would worry? And as for thinking less how I feel, when one is ill all the while, some days not able to get downstairs, one naturally thinks about one’s self and the good time. If one can have a good time when one is ill and stays in one’s room dressed in a kimono all the time, I fail to see where the good time comes in.”

Later in the letter, she says…

“My whole life is ruined and, in a measure, yours is too. Of course it is worse for me than you, but the world and you too may think I am the only one to blame, but somehow I can’t, simply can’t, think I am, Chester. I said no so many times, dear. Of course the world will not know that, but it’s true all the same.”

Despite her time and circumstance, Grace Brown knew what was what. Unfortunately for her, Chester was all she had or at least it appears that’s what she believed. She didn’t stick to her guns.

Like the remorse that comes with a drunk text to an ex, Grace woke the next morning horrified to discover her parents had already mailed the letter. She immediately busied herself with writing another one that night–apologizing for all she had said, asking for forgiveness–still hopeful, still waiting, signing her letters with a pet name–“Kid”–in what seemed like an effort to recapture an intimacy that, it seems, had already vanished.

“I am crying and can’t see the lines and will stop. You will never know, dear, how badly I feel or how much I want you this very minute. With love and kisses. The Kid”

Making Plans

The letters continue.

Grace continues to declare her love and apply the pressure. Chester, when he does write, chooses non-committal sweet talk and manages to masterfully dodge all of her questions and concerns. In fact, he avoids conversation of their predicament almost entirely, choosing instead to write about things like getting a sunburn on a canoe.

On the rare occasion he does bring up the future, he volleys responsibility straight back at Grace.

“…I don’t know where we can or will go. I have really no plans beyond that, as I do not know how much money I can get or anything about the country. If you have any suggestions to make I wish you would and also just when and where you can meet me.”

Fearing the increasing risk of exposure and the social ruin that would inevitably result, Chester realizes he can no longer put Grace off. The time has come to see her again.

Their Adirondack trip begins to fall into place. It is not quite the romantic getaway Grace probably hoped it would be. Rather than come to sweep her away, Chester insists Grace meet him at a hotel and they proceed by train from there. She packed her life into a trunk, boarded a stage and traveled the roughly 10 miles–pregnant and alone.

In her last letter to Chester before they reunite, she writes of saying goodbye to her home and family and all she’s ever known–believing she is beginning a new life with him and, eventually, their child.

“Oh dear, you don’t realize what all this is to me. I know I shall never see any of them again.”

Grace Brown never came back.

American Tragedy

In his introduction to the revised Murder in the Adirondacks, author Craig Brandon talks about the allure of Grace Brown and Chester Gillette’s story; how it’s been called “the murder that will never die.” He talks about the many people who, like himself, have devoted great portions of their lives researching and trying to learn more about Grace and Chester, the sensational trial that followed after the murder and Chester Gillette’s last days before having a seat in the electric chair. He speculates about what continues to drive the fascination with the “American tragedy.”

It’s not a question I can necessarily answer overall, although I have a few ideas–but I can answer it for myself. I was drawn in by the realization that this far-away, century-old murder mystery is rooted in the unfortunate reality that very little has changed. The real tragedy of Grace and Chester’s story is what it reveals about the persistent traditions that rule relationships. Gillian Flynn’s Cool Girl has been around for a very long time.

The circumstances and the language may differ, but the unyielding effort to play it cool–even when there is every reason to do the precise opposite– endures. It is the nature of the game–the price paid for the hope of love, loyalty and happily ever after.

Cynical? Perhaps.

I have lived enough years, though, and had enough conversations with my closest friends to see the unflattering reflection in Grace Brown’s letters–the smudge of the ink. Though a long way from our corseted past, we can still find ourselves very much constricted.

Women are strong and independent and while we probably can “do it all,” we shouldn’t always have to. Relationships, after all, are a two-way street. By definition, you are in them together. We should not have to apologize or be afraid of being exactly who we are and expressing exactly what we feel when we feel it because it might make our partners uncomfortable. We shouldn’t have to worry about driving them away by suggesting they pull their weight. The greatest measure of our worth should not be in our ability to hide ourselves in favor of being breezy, low-maintenence, no drama, so cool. It shouldn’t be considered a weakness or a burden to be human. And if, after all of this, they choose to go–we should let them–without a moment’s pause.

In 1906, holding onto Chester Gillette was imperative for Grace Brown. She truly needed him and she couldn’t bear the idea of bringing shame to her family. The truth is: Chester was always a shitty boyfriend, he was never even a great guy and deep down Grace probably knew it. Her friends at work had tried to warn her. I don’t think she ever could have suspected he was a murderer, until it was too late. Even if she did, he was still her only option. She had to try to make it work. In Grace’s day, and particularly in her situation, a selfish, shitty boyfriend or even a louse of a husband was better than being alone.

Unfortunately, I still know people who think this way.

This, to me, is why this story endures. It is more than just a murder mystery.

I have known a lot of cool girls. I have tried to be one. I can tell you, it works like a charm. It also takes a great deal of energy.

It’s tough to be someone else’s best version of yourself. There is great danger in looking for your best angles in someone else’s eyes, your best words in their mouth, your strength in their backbone, your life in their breath. The results may not be as extreme as losing your life, but you will certainly lose yourself.

Being perpetually “fine” is no way to forge a long-lasting love. No matter how cool you are or how many centuries pass–playing the cool girl will pull you down as surely as Grace Brown. You can only buoy someone so long before drowning.

“…but don’t worry about anything, for I will manage somehow.”
Grace Brown in her last letter to Chester Gillette, 1906
Chester Gillette and Grace Brown

Chester Gillette and Grace Brown


Note: I have only scratched the surface, obviously, of the full story of Grace Brown and Chester Gillette. If you are interested in learning more about the case, I strongly encourage you to read Craig Brandon’s book, Murder in the Adirondacks: An American Tragedy Revisited–preferably purchased from your local bookseller!

Digiprove sealCopyright secured by Digiprove © 2016 Kate Welshofer


  1. Megan
    July 11, 2016 / 2:17 PM

    I’ve always loved that story since all of those locations are close to where I grew up! Great blog:) PS that book store sounds amazing; as someone who also owns no electronic devices upon which to read, I wish we had one of those around here!

  2. Don
    July 12, 2016 / 10:11 PM

    Hi, Kate. Great to see you writing again! I enjoyed the piece. You’ve piqued my my interest. I’ll have to buy the book and give it a read.

  3. John Gearing
    September 5, 2016 / 1:53 PM

    As always, Kate, a deeply considered, well-reasoned piece that made me stop and think. If I may, I’d like to add that men need a wake-up call too. Because for every “cool girl” there is a man who is expecting her to be “the cool girl,” who wants her to be not herself, but to pretend to be the woman he wants her to be. And he expects her to find happiness and fulfillment in this role, and to eventually lose herself and become that woman. I’m reminded of my 20’s, when it seemed that girls were only attracted to guys who defined their lives for them this way. Not all girls, for sure, but enough that my male friends remarked on it while we lamented our lack of girlfriends. Fellow men, give it up! Try to stop the cycle and instead get in touch with the actual, true woman. Take off your mask and help her take hers off. Will it be scary? Hell yeah it will. It’s unexplored country and you’re going to get to know each other all over again. Will the relationship survive? No guarantees – but if not take comfort in accepting that if she had to suppress herself in order to “make it work” then it wasn’t really working, and hopefully the lessons learned in the process will help you find future joy with a woman who lives her true, honest self even though she loves you.

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