What Makes a Great President?

On a day created to honor George Washington, we're now supposed to celebrate every scoundrel, criminal, and creep to occupy the Oval Office. My new book assesses the worst presidents, and the best.

Atlanta, GA

February 16, 2026

[NB: The following is excerpted from the Introduction to my new release, Unconventional Wisdom: The Best and Worst U.S. Presidents, now available here.]

Years ago, tired of conventional wisdom and political propaganda, I wrote some sketches of prominent presidents to whom almost everyone pays reflexive homage.

As I did, I realized that the universal admiration (or revulsion) many of these men receive says more about our modern sensibilities than it does of the constitutional merits of any president’s performance.

Most of the men we’re supposed to consider “great” regularly engaged in outright atrocities and undertook actions that in the private sphere would be condemned as criminal. But because these acts were committed from behind a presidential seal, the repulsive policies made “statesmen” of the executives who authorized them.

Likewise, the presidents Court historians least respect are those who held back, respected limits, and deferred to state or legislative authority. Our modern Plutarchs view these men as weaklings who shrank from the moment. Accordingly, they occupy the bottom rungs of the presidential rankings.

Alter-Ego

Everyone likes to compile and argue about lists: Who are the best pitchers of all time? The greatest quarterbacks? Our favorite cities? Best composers? Greatest basketball player? Top movies? Best rock albums? Best winemakers? Favorite books?

These are the debates we love to have, at the bar, over dinner… or in silly essays. In this volume we consult our inner-Schlesinger, and catalog the most worthy and repulsive U.S. presidents. But our inner-Schlesinger is an alter-ego of those Establishment historians… père et fils… who popularized presidential rankings in the 20th century.

Unlike those hagiographers, we are wary of righteous rulers, and contemptuous of those who have all the answers to every problem… most of which they themselves imagined or caused. We want leaders who appreciate their own ignorance and respect their own doubts. We value humility over grandiosity, fidelity above certainty.

We shouldn’t honor presidents per se. Having a holiday for them seems un-American. The annual commemoration had an honorable origin. But, like fine wine at a frat party, it was defiled, diluted, and debased till it finally went bad. It has been perverted from a worthy occasion honoring a great man into a long weekend commemorating an assortment of awful ones.

Subterranean Speakeasy

The third Monday in February is still officially designated Washington’s Birthday, but is known colloquially as “Presidents Day”, as if being president was Washington’s most notable accomplishment.

The best thing he did as president was to stop being president. Voluntarily giving up power after a second term set an admirable precedent, and echoed his earlier act of relinquishing his commission and retiring his sword.

When he did so, King George couldn’t believe it. “If this is true”, said the mad monarch, “then he is truly the greatest man who ever lived.”

Washington was a great man. But was he a great president? Relative to the host of charlatans, hacks, and crooks that infest our own era, he was Solon and Solomon rolled into one. Still…like a subterranean Speakeasy…that’s a low bar.

Our criteria will be loftier, yet simple. We will judge presidents by how well they upheld their oath of office, how much wealth they left untouched, and how few people they managed to kill. That alone should whittle from the list most of the deadwood that’s piled up since Calvin Coolidge.

Let’s start with this disclaimer: I don’t think there should be a president. I am more a fan of the Articles of Confederation than of the US Constitution.

I realize that under the Articles there were eight presidents “under Congress assembled”. But none of them ever presumed to launch a war or meddle in the affairs of individual citizens. We don’t know who they were. Most alive at the time didn’t either. That’s as it should be.

But even under the Constitution, we’d probably be fine if only that moribund document were followed. Alas, it hasn’t been for over a century and a half.

Rouge’s Gallery

Yet that doesn’t let the Constitution off the hook. As Lysander Spooner said, the Constitution either permits what has happened or has been powerless to stop it. Either way, it is unfit to exist.

But it does exist…on paper at least. And it includes a president. Since the Constitution was adopted, there have been forty-five of them (not forty-seven: Grover Cleveland wasn’t two different guys; neither is Donald Trump).

It’s hard to come up with ten good presidents, and difficult to limit ourselves to ten bad ones. Since the branches hang heavy with foul fruit, let’s first relieve the tree of its rotten apples.

A good heuristic when evaluating presidents is that the ones Academia, the Literati, and establishment historians consider “great”…those who are universally admired by both sides of our narrow political spectrum …are almost invariably scoundrels. As Lord Acton said, “great men are almost always bad men.”

Which brings us, in chronological order, to our rouge’s gallery…with a brief explanation of why each reprobate made the roster.

Without further ado, let’s begin the lists, which can be found (with in-depth overviews of each entry on both rosters) in this book (or click image below):

JD