Jan. 9, 2026

Two Grifters Walk Into a Bar: When Tall Tales Meet High Finance

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Let’s be clear from the start: neither Calamity Jane nor Donald Trump ever met a fact they couldn’t improve upon. One peddled her autobiography in saloons for drinking money. The other turned his into a real estate empire and the presidency. But strip away the period costumes and the tax returns, and you’re looking at the same con in different centuries.

Martha Jane Cannary, aka Calamity Jane, made her living as a prostitute in frontier towns, though she’d spin yarns about being a Pony Express rider or Army scout for General Custer. She was arrested repeatedly in Cheyenne, Miles City, Rawlins, Laramie, Livingston, and Billings for drunk and disorderly conduct, prostitution, and general mayhem. The woman had twelve variously reported husbands and would hawk copies of her own fictional biography when cash ran dry. She claimed to have confronted Wild Bill Hickok’s killer with a meat cleaver—he’d already been arrested an hour earlier. After Edward Wheeler immortalized her in dime novels, Jane published her autobiography in 1896, a masterwork of semifiction where she claimed heroic deeds that somehow left no witnesses or documentation. When work dried up, she’d travel the country performing in Wild West shows, then stand outside selling photographs of herself and copies of that glorious work of fiction.

Donald Trump was convicted on 34 felony counts of falsifying business records, found liable for sexual abuse with $88.3 million in damages to E. Jean Carroll, and found liable for business fraud. His livelihood consisted of inflating property values, slapping his name on buildings, and convincing banks his triplex was three times its actual size. He inherited between $413 million and $600 million from his father, then squandered much of it through overleveraged casino ventures that went bankrupt, Trump Steaks that flopped, and Trump University that got sued for fraud. His ghostwriter Tony Schwartz coined the phrase “truthful hyperbole” to describe Trump’s approach. Trump Tower? Added extra floors to the count. Mar-a-Lago? Valued it at up to $612 million when the actual assessed value was around $75 million. He turned bankruptcy into a business model, fraud investigations into witch hunts, and 34 felony convictions into evidence of persecution.

Both figures understood something fundamental about America: we’re suckers for a good story, especially if it’s told with absolute conviction by someone who believes their own lies. Martha Cannary was an illiterate woman who worked as a prostitute, cook, and laundress in frontier towns. She drank heavily, got arrested regularly, and lived in what contemporary observers called “the most horrid and debased condition.” The romantic relationship with Wild Bill Hickok? Wishful thinking. The heroic rescue of Captain Egan? Her own invention. Historian James McLaird concluded that Martha Cannary was “an ordinary woman with little that would merit special interest”—except for her extraordinary talent at self-mythologizing. Trump inflated his wealth by as much as $3.6 billion in one year, turned his triplex’s 10,996 square feet into 30,000 square feet on paper, and valued properties at whatever number served him best that particular Tuesday. A federal judge characterized him as “a prolific and sophisticated litigant who is repeatedly using the courts to seek revenge on political adversaries.”

A Hypothetical Meeting: The Gilded Age Saloon

Deadwood, 1885. A different timeline. Trump, somehow transported back in time by a freak golf cart accident involving a DeLorean, walks into a saloon. The place smells of whiskey, sweat, and wood smoke. At the bar, a woman in men’s clothing nurses a bottle, already three sheets to the wind.

Trump surveys the room with visible disgust. “What a dump. I could buy this place, tear it down, put up something classy. Gold fixtures. My name in lights. ‘Trump Gulch.’”

The woman at the bar turns, squinting through her alcoholic haze. “Who the hell are you, fancy pants?”

“Donald Trump. The greatest businessman you’ve never heard of because you’ll be long dead when I’m famous. I’m rich. Very rich. Probably the richest man you’ll ever meet.”

Calamity Jane laughs, a raspy sound that turns into a cough. “That’s funny. I just sold a fella a story about how I saved the entire cavalry from a Sioux ambush single-handed. Got five cents for it and a whiskey. What’d your last lie get you?”

“Forty million in loans from Deutsche Bank.”

Jane squints harder. “What’s a bank?”

“It’s like a saloon but for money. You tell them you’re worth a billion dollars, they give you loans, you spend the loans, then you tell them it’s their fault for believing you.”

“Huh.” Jane takes another swig. “I just tell folks I knew Wild Bill real intimate-like and they buy me drinks. Simpler.”

“Did you?” Trump asks, leaning against the bar.

“Hell no. He thought I was a nuisance. But nobody checks.”

Trump’s eyes light up. “Nobody checks. That’s genius. You should write that down.”

“Can’t write.”

“Even better! That’s what I have people for. Lawyers, accountants, ghostwriters. The trick is to make sure they can’t testify against you later.”

Jane grins, showing gaps where teeth used to be. “I like you. You’re as full of shit as I am.”

“The most full of shit,” Trump corrects. “Nobody’s ever been fuller of shit than me. People say it all the time.”

“Want to go partners? I’ll tell stories about fighting Indians, you tell stories about... whatever it is you do.”

“Real estate. Buildings. Very tall buildings with my name on them.”

Jane looks confused. “Buildings you already built?”

“Not yet. But once I describe them, they basically already exist. That’s called vision.”

Jane nods slowly, a dawning recognition in her eyes. “And once I describe myself saving that captain, I basically already did. That’s called whiskey.”

“I think,” Trump says, gesturing to the bartender for two drinks, “we just invented American entrepreneurship.”

“I think,” Jane replies, “we just invented American politics.”

They toast. Neither pays for their drinks. The bartender will spend the next twenty years trying to collect. Jane slumps back over the bar, already spinning her next tale for the next sucker. Trump straightens his tie and walks back out into the dusty street, already calculating how much he could sell the whole town for if he claimed to own it.

The meeting lasts fifteen minutes. The con they recognize in each other will last forever.

The Scale of the Scam

Here’s where the comparison gets uncomfortable: Calamity Jane’s lies were small-time grift that got her drinking money and a pauper’s grave. She hurt herself more than anyone else, dying broke and alcoholic at 47 in a Montana mining town, buried next to a man who probably didn’t love her. Trump’s lies had consequences that echoed through markets, courts, and the political system itself. Banks made loans based on fraudulent statements, investors lost money on schemes that collapsed, and charges that a federal prosecutor said had sufficient evidence to “obtain and sustain a conviction” for attempting to overturn an election disappeared only because you can’t prosecute a sitting president. Jane exaggerated her goodness and her badness in equal measure, seeking attention and drinking money. Trump exaggerated his wealth and his victimhood in equal measure, seeking power and immunity from consequences. One sold photographs. The other sold a country on the idea that the truth is whatever you’re confident enough to say.

What makes both figures quintessentially American is this: we made them famous for it. We bought the photographs, we elected the president, and we turned their fabrications into folklore and their fraud into politics as usual. Edward Wheeler made Calamity Jane a dime novel hero, reality television made Trump a boardroom genius firing people who had worked for him. The media ecosystem that elevated Jane’s tall tales was penny dreadfuls and traveling shows, the media ecosystem that elevated Trump’s was cable news and Twitter. The technology changed. The scam didn’t. Neither figure would exist without our collaboration. We’re not victims of the con—we’re participants. We want the myth more than we want the truth, we want to believe that a dirt-poor frontier woman was a hero or that a mediocre real estate heir was a genius. We want the story to be better than the facts.

The tragedy isn’t that Martha Cannary lied about her life. It’s that the lies were more interesting than what she actually did—which was survive impossible circumstances as a woman alone on the frontier, show occasional compassion to the sick, and maintain a sense of humor about her own bullshit.

The tragedy isn’t that Donald Trump lied about his wealth. It’s that we rewarded him for it at every turn—with loans, with fame, with power—until lying became not just profitable but presidential.

They’re both master class practitioners of the same fundamentally American art: inventing yourself out of whole cloth and selling the pattern to anyone who’ll buy it. One ended up in a grave in Deadwood. The other ended up in the Oval Office.

Different centuries. Different consequences. Same grift.

And we keep falling for it.

FTS