George Wallace. Henry Ford. Hitler.

No, it’s not the start of a bad joke. These are just a few of the historical figures to whom critics are comparing Donald Trump.

Of course, finding an exact precedent for Trump is a futile exercise. History is not a cycle that repeats itself over and over, but rather a never-ending continuum filled with intersecting layers. Think of it as less of a carousel, and more of a roller coaster that keeps adding new twists and turns, much to the discomfort of its nauseated passengers.

Still, historical comparisons are useful in examining how elements of the Trump phenomenon work. One of the most puzzling questions about Trump has been his knack for political mobilization. How has a widely panned candidate managed to gain such a substantial following? The answer lies in the strategy of another polarizing leader: William “Boss” Tweed.

Both men built a fervent political base out of a single demographic to which they did not belong. By focusing on the special interests of that neglected group, Tweed and Trump found success in a political climate that otherwise would’ve labeled them as crooks and liars.

Tweed’s Tammany Hall machine relied on securing the votes of recent immigrants, particularly the Irish. In an environment plagued by poverty and nativism, Tweed smelled opportunity. He and his colleagues created an early welfare system that supplied the immigrants with food, jobs, and housing in exchange for political support. Historian Kenneth D. Ackerman writes that Tammany Hall provided “state money for schools and hospitals, lumps of coal at Christmas, and city patronage jobs to put bread on family dinner tables.” Though the self-serving motives behind Tweed’s generosity were clear, New York’s poor continued to back him based on the simple fact that he made their lives better when other politicians just didn’t seem to care.

Tweed and his cronies used their growing power as an opportunity to embezzle thousands of dollars from public projects, most infamously through a phony renovation to the City Court House. Nevertheless, Tweed never viewed his theft as an immoral act. It was business, and he was good at it. Towards the end of his life, Tweed explained, “The fact is New York politics were always dishonest, long before my time. There never was a time you couldn’t buy the Board of Aldermen […] A politician coming forward takes things as they are.”

Sound familiar? Trump has similarly used bankruptcy laws and eminent domain — meant for “public use” — to his advantage.

Trump’s outspoken beliefs and motivations have already earned him the spite of many fellow billionaires, but he doesn’t seem to care. Instead, he has established his base among the less-educated, blue-collar voters across the country.

With promises to secure jobs at home and kick ISIS’s ass abroad, Trump has amassed a committed base of support. Based on a New York Times analysis, Trump support correlates strongly with white people who ethnically identify as “American,” those without high school degrees, and those who live in mobile homes.

Many of Trump’s supporters look to him as a paternal figure capable of redirecting America’s wealth back to its forgotten citizens. Paul Weber, an attendee of a Trump rally in Iowa, complained that recent immigrants are “getting pregnant and coming here and having babies,” allowing them to “get everything and the people that were born here can’t get everything.” Many also chalk up Trump’s personal success, multiple declarations of bankruptcy notwithstanding, as a sign that he would have better control over economic fluctuations. “I like him because he’s a businessman,” explained Trump enthusiast Linda Wilkerson. She added, “We’re in terrible financial debt. I hope he can bail us out.”

So, what can we expect from Trump based on Tweed’s trajectory? For one thing, Tweed’s subsequent downfall demonstrates just how fragile Trump’s popularity may be. He too is dependent on single group’s allegiance, and any hit to his tough-guy reputation could prove fatal. It’s just like that old saying about putting all your eggs—or Trump steaks—in one basket.

But where will this decisive blow come from? Trump’s media presence, currently one of his greatest assets, could become his undoing.

Like Trump, Tweed had a less than amicable relationship with the mainstream media. Perhaps in another world, the two men would meet in a penthouse to sip some vintage brut and scowl at caricatures of bloated bellies and bad comb overs.

Tweed was a favorite target of cartoonist Thomas Nast, nowadays most famous for his design of the modern Santa Claus. Nast portrayed Tweed as a sleazy criminal who stole funds from public projects while wearing a diamond on his shirt and a money sack over his head. The efforts of Nast and other journalists eventually exposed Tweed’s fraudulence and damaged his popularity among immigrants. He died penniless and imprisoned in 1878.

So far, Trump has dodged every media attack, somehow turning each gaffe and insult into a display of American authority. However, Trump will not be as invulnerable should he ever have the responsibility to govern. He has little to lose as an outsider candidate, but any corruption in office would reveal him as the hypocrite he is.