William M. "Boss" Tweed stole so much money from New York City that historians still argue about the exact amount.
This is not because the records are unclear. It is because the number eventually becomes difficult to comprehend. Somewhere between thirty million and two hundred million dollars, depending on whose accounting you prefer, the human brain simply stops distinguishing between categories and settles on "a lot."
For more than a century, Tweed has occupied a special place in the American imagination. He is corruption in its purest form. The cigar-smoking political boss. The embodiment of machine politics. The villain in every high school textbook chapter about Gilded Age government.
This is why I suspect he would be delighted by modern campaign finance.
Not because it resembles Tammany Hall.
Because it surpasses it.
One can almost imagine Tweed reviewing the modern system the way an aging craftsman examines a newer model of his favorite tool.
First comes confusion.
Then admiration.
Then professional jealousy.
To understand why, it helps to understand what Tweed actually did.
Popular memory often treats him as a common thief who happened to enter politics. In reality, Tweed was something more interesting and considerably more American.
He built a machine.
Tammany Hall was not simply a corrupt organization. It was a political ecosystem. It found jobs for immigrants, delivered coal during hard winters, assisted widows, helped newcomers navigate city bureaucracy, and provided services that government often failed to provide. In return, it expected loyalty.
This arrangement was not especially noble.
Nor was it especially unusual.
Politics throughout much of the nineteenth century functioned through relationships, favors, patronage, and personal connections. Tweed simply became extraordinarily successful at it.
His famous observation remains one of the most honest statements ever uttered by an American politician:
"I don't care who does the electing, so long as I get to do the nominating."
Corruption, Tweed understood, is rarely about voting.
It is about access.
Modern Americans often imagine corruption as a suitcase full of cash changing hands in a dark room.
This is largely because movies have been tremendously successful.
Actual influence is considerably less cinematic.
Influence looks like a phone call returned promptly.
Influence looks like a meeting granted.
Influence looks like a donor reception.
Influence looks like a relationship.
Influence rarely arrives carrying a sign announcing itself.
That was true in Tweed's New York.
It remains true today.
The difference is scale.
Tweed needed ward bosses.
Tweed needed precinct captains.
Tweed needed newspaper editors.
Tweed needed contractors, saloon owners, businessmen, and neighborhood organizers.
Influence required an enormous amount of labor.
Modern America has streamlined the process.
Somewhere along the way, influence became an industry.
The ward bosses disappeared.
The consultants arrived.
The cigar smoke cleared.
The PowerPoint presentations multiplied.
One suspects Tweed would be particularly impressed by the language.
Nineteenth-century corruption spoke plainly.
Bribery was bribery.
Patronage was patronage.
Political machines were political machines.
Modern influence has acquired an entire vocabulary capable of anesthetizing the reader.
Independent expenditures.
Issue advocacy.
Political action committees.
Dark money organizations.
Regulatory compliance structures.
This is remarkable progress.
Nothing survives public scrutiny quite like terminology that sounds like a tax seminar.
The truly beautiful part, however, is that modern politics has accomplished something Tweed never could.
It has convinced nearly everyone that influence exists only on the other side.
Republicans believe wealthy Democrats distort politics.
Democrats believe wealthy Republicans distort politics.
Populists oppose special interests.
Special interests oppose other special interests.
Everyone is furious about money in politics.
Everyone is absolutely certain their preferred donors are the exception.
The system has achieved a level of sophistication that would have brought tears to Tweed's eyes.
Mark Twain once remarked:
"There is no distinctly native American criminal class except Congress."
This was unfair.
Congress has always contained many respectable people.
The problem is that Twain understood something essential about American politics.
We dislike corruption in theory.
In practice, we often object primarily to corruption benefiting someone else.
This is one reason political reform has always proven so difficult.
Every generation wants cleaner government.
Few generations wish to surrender influence.
To be clear, modern America is not uniquely corrupt.
The Athenians dealt with influence.
The Romans dealt with influence.
The British Empire dealt with influence.
The founders dealt with influence.
Politics is ultimately the allocation of power, and power attracts people who wish to shape its distribution.
The interesting question is not whether influence exists.
The interesting question is how honestly a society discusses it.
And here modern America becomes fascinating.
We have created a political culture in which nearly everyone understands the game while simultaneously pretending the game is not being played.
This would have baffled Tweed.
Tammany Hall was corrupt, but it was rarely subtle.
Modern influence often arrives wrapped in mission statements, legal disclaimers, and patriotic branding.
The machinery remains.
The packaging has improved.
Imagine explaining the modern system to Tweed.
"Large donors spend millions attempting to shape public policy."
"Naturally."
"They fund organizations that run advertisements."
"Reasonable."
"They hire lobbyists."
"Expected."
"They cultivate relationships with politicians."
"Of course."
"They insist none of this affects anything."
At this point Tweed would probably begin laughing.
And he would not stop for some time.
For generations, Americans have treated Boss Tweed as a warning from history.
A reminder of what politics becomes when influence operates unchecked.
This is fair enough.
History should contain villains.
But after examining the modern system, one suspects Tweed might feel less like a relic and more like an ancestor.
Not because modern America resembles Tammany Hall.
Because it has refined many of the same incentives.
Tweed's machine ran on favors, relationships, access, and influence.
So does ours.
The technology changed.
The scale changed.
The terminology improved.
The spreadsheets became more impressive.
But the underlying machinery remains surprisingly familiar.
One imagines Tweed surveying the landscape, removing his cigar, and offering a final verdict.
"Ladies and gentlemen," he would say.
"We've done it."
And for perhaps the first time in American history, everyone would immediately understand exactly what he meant.
— John Handcock