Ask Not Why I’m Screaming: The Kennedy Legacy Is Even Uglier Than You Think
Reading Maureen Callahan’s “Ask Not” Broke My Brain
Let me start by saying this: I am not easily shocked. I write for a living. I devour scandals and memoirs like they’re late-night snacks. I’ve inhaled my fair share of juicy nonfiction and come out the other side rolling my eyes.
But Ask Not: The Kennedys and the Women They Destroyed by Maureen Callahan?
This one scorched my soul.
What Callahan does in this book is less biography and more autopsy. She doesn’t romanticize the Camelot myth. She rips it wide open—detailing how the Kennedy family used women as PR accessories, emotional punching bags, and collateral damage in their pursuit of power. And then they rewrote history to make themselves the heroes.
Buy it at your own risk: Ask Not: The Kennedys and the Women They Destroyed
A Black Hole Where Camelot Once Lived
If you were raised on the glossy image of JFK and Jackie—the grace, the tragedy, the perfect photo ops—this book will claw into that perception and burn it from the inside out.
Here’s just a taste of what Callahan digs into:
John F. Kennedy slept with anything that moved, including his staffers, random teenagers, and women his friends trusted him with.
Bobby Kennedy, the so-called moral compass of the family, was tangled up with Marilyn Monroe, too—just like his brother.
The family weaponized their power, hiding sex scandals, suicides, affairs, and breakdowns like they were stocking a vault labeled Do Not Open Until Never.
Maureen Callahan doesn’t just tell you what happened—she shows you exactly how the Kennedys got away with it.
Marilyn Monroe: Used, Abandoned, Silenced
We all know the whispers: Marilyn and JFK. Marilyn and Bobby. The birthday song. The overdose.
But Ask Not pulls the curtain back in a way I wasn’t emotionally prepared for. Marilyn wasn’t some fame-hungry mistress. She was a woman crushed by proximity to power. She knew too much. She asked too many questions. She stopped playing the game—and paid for it with her life.
Callahan connects dots you can’t unsee. The timeline, the political motives, the sheer ruthlessness—it’s not a conspiracy theory. It’s a pattern.
JFK Jr. & Carolyn Bessette: The Fairytale That Wasn't
I went into this section thinking it might be lighter. It wasn’t.
We remember them as icons: John F. Kennedy Jr., the People’s Prince, and Carolyn Bessette, the impossibly stylish wife. But Callahan strips away the fantasy. Their relationship was toxic. Publicly adored, privately unraveling.
JFK Jr. reportedly screamed at her in public, in front of friends.
Carolyn was isolated, deeply unhappy, and hounded by paparazzi.
Their plane crash? Callahan outlines it with brutal, beautiful precision—making it clear this wasn’t just tragedy. It was inevitability.
Why Didn’t I Know Any of This?
Seriously—why weren’t we told? Why was this all buried under magazine spreads and presidential quotes? Why were the Kennedys canonized while the women they destroyed were turned into cautionary tales?
Callahan’s book forces you to confront the truth: the Kennedy legacy isn’t just built on charisma. It’s built on erasure. And once you see it, you can’t go back to Camelot.
My Emotional Support Read-Along: Cheer Denise on YouTube
Look. I didn’t read this book alone. I couldn’t. There’s too much devastation per chapter.
Which is why I highly recommend reading it alongside Cheer Denise, a YouTuber who has become my absolute rock through this experience. She reads the book chapter by chapter, adding commentary, gasping when you gasp, and generally validating every breakdown I have while turning the page.
▶️ Watch her read Ask Not here: Cheer Denise on YouTube
It’s part literary therapy, part rage-fueled book club, and completely addictive.
So What Do We Do With All This?
We tell the truth.
We stop romanticizing men who treated women like disposable PR strategies. We stop pretending that being powerful excuses being cruel. We stop letting legacy whitewash abuse.
And we keep reading books like Ask Not, even when they make us feel raw. Especially when they do.
Because in the wreckage, we find what was buried: women with voices. Women with stories. Women who deserved more.
