The Great American Grift: A Dynasty of Corruption

Illustration showing historic American corruption alongside modern political profiteering by the Trump family. — The Great American Grift

The Great American Grift: From Bootleggers to Billionaires, and the Dynasty Now Steering the Ship of State

If there’s one tradition that has endured from America’s first plundered acre to its latest golden penthouse, it’s this: the richest families in the country rarely made their fortunes in ways you’d call clean. At the top of the national mythology are the titans families whose wealth was built not on brilliance or innovation but on schemes, strong-arming, and the dark arts of early capitalism.

The Rothschild banking “innovations,” the Kennedy bootlegging empire, the Gambino crime family, the Medellín cartel. The Sacklers, high society’s genteel drug dealers who pumped OxyContin into the bloodstream of a nation. Jay Gould, the robber baron’s robber baron, who traded in bribery, collusion, and market manipulation with the enthusiasm of a man collecting rare wines. Rockefeller, once the richest man on earth, perfected monopolization and corporate espionage so thoroughly he all but wrote the playbook.

And then there were the American opium kings: John Jacob Astor, John Murray Forbes, Samuel Wadsworth Russell, Warren Delano (yes, FDR’s grandfather), and the Perkins clan, families who rode the 19th-century narcotics trade to dizzying heights of respectability.

This is the American origin story nobody puts in textbooks: genocide, slavery, and every shade of profiteering in between. The path to great wealth has never been lined with virtue. It has always been paved in vice.

Enter the Trumps: America’s Most Persistent Family Business

Which brings us, inevitably, to the Trumps, one of the most ethically compromised dynasties in modern U.S. history.

The saga begins with Friedrich Trump, the “adorable” grandfather of our esteemed modern political protagonist. After failing to complete mandatory military service, he was effectively told not to return to Germany once he had emigrated to the U.S. in 1885. When he attempted to move back years later, German authorities bluntly rejected him. So he fled, much like his grandson would nearly a century later from Vietnam service back to the United States, new bride in tow.

By then Friedrich had already made a tidy fortune in the Canadian Northwest by providing two essentials to lonely miners: sex workers and liquor, both illegal. In Washington State, he perfected a second hustle, filing a gold claim on land already claimed by another, then using the loophole to build a boarding house instead of mining it. A Trump tradition emerged early: find the crack in the system—then widen it by force.

He died in the 1918 influenza epidemic, leaving the family business to his 15-year-old son, Fred Trump Sr., who built an empire not through brilliance but through the abundant generosity and loopholes of the U.S. government.

The Fred Trump Era: Subsidies, Scandals, and Systemic Discrimination

Fred Trump Sr. became one of New York’s most prolific builders, using government programs intended for returning veterans to create what was essentially a personal machine for manufacturing profit.

Government Money, Maximum Extraction

FHA-Backed Loans: Fred leveraged federal guarantees to build tens of thousands of homes.
Cost Inflation: Senate investigations in the ‘50s and ‘60s found he systematically inflated building costs to pocket “windfall profits.”
1954 Senate Report: Found that Trump and associates siphoned off millions more than the government intended.
1966 State Probe: Revealed illegal profit-routing through equipment-rental scams on Trump Village.

The Art of the Tax Dodge

A New York Times investigation later documented “dubious tax schemes” and outright fraud used to funnel an estimated $400 million (in modern dollars) to Donald Trump and his siblings tax-free. The dynasty’s second golden rule emerged: Never pay a dollar you can stash offshore instead.

Discrimination and the Klan

Fred also left a trail of racial exclusion:

1973: The Justice Department sued Fred and Donald Trump for systematic violations of the Fair Housing Act.
Evidence: Black tenants labeled “C” for “colored”; fake “no vacancy” scripts; white tenants ushered in with ease.
Outcome: A consent decree, followed by continued noncompliance.

And in 1927, Fred Trump was arrested at a Ku Klux Klan rally in Queens, a detail the family insists was either mistaken, irrelevant, or both, yet which lingers like smoke in a closed room.

The Donald Era: Fraud, Foreign Money, and the Monetization of Public Office

If Fred built the machine, Donald industrialized it.

His business record, now confirmed in court includes:

The New York Fraud Case: A sweeping 2024 judgment found Trump, his sons, and his company guilty of a years-long pattern of fraudulent asset inflation designed to secure better loans and lower insurance costs.
Trump University: A $25 million settlement for defrauding thousands.
Tax Schemes: Consulting fees funneled to his daughter, questionable write-offs, and a tangle of evasion.

Profiteering from the Presidency

Donald Trump’s refusal to divest from his businesses made the presidency the most lucrative family venture yet:

Emoluments Concerns: Foreign governments and state delegations booked rooms in Trump hotels while seeking favor.
Self-Dealing: Government events held at Trump properties; diplomatic meetings staged in Trump ballrooms; Secret Service forced to pay Trump-owned resorts for lodging.
New “Ethics Agreement”: For his current term, the Trump Organization now allows foreign private deals—an open invitation for influence shopping.

Criminal Exposure

Trump now faces criminal charges in multiple jurisdictions tied to:

Election Subversion (Federal & Georgia)
January 6
Classified Documents Mishandling (Florida)
Business Record Falsification (New York)

This is, by any measure, the most legally embattled family ever to sit atop the American government.

A Dynasty With a Country at Its Disposal

The irony is that Americans have watched the same story unfold for 250 years and continue to feign surprise. The wealthiest families, colonial opium merchants, Gilded Age robber barons, modern corporate pushers—have always skirted or shattered the law for profit.

But never before has a family with this level of documented corruption had direct control over the nation’s secrets, global alliances, public funds, and the levers of justice itself.

Never before has the great American grift been granted a West Wing suite.

The tragedy is not that this is happening again. It’s that, once more, the country refused to learn from its own history.

Why It Matters

The Trump dynasty does not represent a break from America’s history of corruption—it is the culmination of it. For the first time, a family with a documented, multigenerational pattern of fraud, exploitation, tax evasion, and profiteering is not merely influencing the political system but running it. A nation cannot remain free when private criminal enterprise merges with public power.

Key Takeaways

America’s wealthiest families—from robber barons to drug empires—built fortunes through exploitation, not innovation.
The Trump dynasty fits squarely into this pattern: fraud, tax schemes, discrimination, and foreign money.
Trump has commercialized the presidency more aggressively than any leader in U.S. history.
The family now wields both private financial networks and state power—an unprecedented threat.
What appears new is actually old: America repeatedly rewards corruption—but never before at this scale.