March Madness 2024, Presidents Edition! Part 1

What is Presidential March Madness?

In 2019, I came across the idea of hosting “bracket nights”—creating a single-elimination bracket for any subject matter area and gathering with friends to debate each matchup until one champion remains. Topics could include great scientists, statesmen, foods, amusement park rides, pretty much anything. Alas, the pandemic would scuttle bracket nights, along with most all other social plans.

The idea has remained one that greatly intrigues me, and I’ve decided to apply it to former U.S. presidents in a series of posts, in the spirit of the annual March Madness basketball tournaments going on around this time. Here’s how it’ll work.

I’ll seed all former U.S. presidents in a 44-man bracket, divided into 4 quadrants of 11 each. Note that I’m excluding current president Joe Biden, both to avoid recency bias and to avoid judging him on only a portion of his time in office.
Seeding will be based on this historical survey from 2021. I’m not endorsing these rankings, but we need a place to start for seeding—upsets can always happen!
The first four posts in this series will cover one quadrant each, through the round of 16.
The final post will cover the eight quarterfinalists.
Each quarter of the bracket will be named for the top-seeded president in that quarter:
- 1: Abraham Lincoln
- 2: George Washington
- 3: Franklin D. Roosevelt
- 4: Theodore Roosevelt

Of course, any exercise like this is highly dependent on what kind of criteria we use. For instance, our authors of Patriot’s and People’s would likely have very different outcomes if they participated. Because of this, I encourage my readers to think through how you would decide each matchup differently, and what criteria you’re implicitly using. And if you differ strongly with any of my conclusions, mention it in the comments.

Here are my criteria, up-front and defined. As always, there’s a tradeoff between thoroughness and clarity. There are seven criteria: whichever president in a single matchup has the better record in four or more will win the matchup.

Foreign Policy & Crisis Management. This includes actions taken to win or avoid wars, as well as efforts in navigating/preventing emergencies both at home and abroad.
Consistency with American Ideals & Constitution. This refers, not only to the Constitution itself, but America’s other founding documents (the Declaration and the Federalist Papers, for instance). Part of the executive’s function is to uphold the ideas America is founded on: consent of the governed, equality before the law, and limits of governmental and executive power.
First Citizenship & Contributions Out of Office. A good president avoids personal misconduct and retains some level of moral legitimacy. Also, a president’s contributions to America (or humanity) either before or after their time in the White House will be considered here.
Having & Articulating a Vision for America. Another two-part criteria. It is not sufficient to simply have a vision so much as convey one, both to colleagues in government and the American people.
Contributions to Prosperity. On some level, this encapsulates Reagan’s challenge to Jimmy Carter in the 1980 election: “Are you better off now than four years ago?” Of course, many such factors of well-being are outside presidential control, but the well-being of citizens is an area that governments should be judged upon.
Minimizing Externalities. Many government actions have long-reaching consequences that will outlive the president who oversees their first implementation. In this category, there are bonus points for leaving the country “better than you found it”, and penalties for leaving a successor stuck holding a ticking time bomb.
Vice President/Cabinet. I think it’s fitting that in the event of a 3-3 tie in the other six points, the quality of a president’s VP and cabinet should decide the matter. Especially as the executive branch has grown, it’s critical for presidents to surround themselves with conscientious and competent people.

One more procedural note: the numbers next to each president’s name refer to their rankings in the C-Span survey, not their chronological order.

With no further ado—let’s jump into the Madness!

Lincoln’s Quarter—Play-In Round

(32) Benjamin Harrison vs. (33) Rutherford B. Hayes

These two presidents, both Republicans, served single terms only a few years apart from each other in the late 19^th century. Hayes frequently gets a bad reputation for the “backroom” deal that brought him into office when the 1876 election was thrown into the House of Representatives. The result of this was a premature end to federal occupation in the postwar south, which left many freed blacks to fend for themselves. Because of this, we have to penalize him for the externalities this left to subsequent presidents. Also, Hayes sent federal troops to break up labor strikes in Pittsburgh, ostensibly to protect government buildings.

Neither president had major contributions outside of office. Both served in the Union volunteers, with Hayes rising to a slightly higher rank. Hayes’ administrators laid the groundwork for much of what would become the “modern” policy toward American Indians. While both held similar party platforms, Hayes took more decisive actions to limit corruption in government.

Final result: Hayes wins, 5-2.

(25) Grover Cleveland vs. (40) William Henry Harrison

Good old William Henry Harrison gets a raw deal in this one—that’s what happens when you die of pneumonia after thirty days on the job. It doesn’t help that he goes up against one of the more principled and less partisan presidents of the 19^th century—I maintain that Cleveland is underrated.

This is no sweep, though. While Cleveland insisted on being honest when accused of extra-marital affairs, Harrison’s military service during the War of 1812 gives him something to show for his career.

Final result: Cleveland wins, 6-1.

(24) Calvin Coolidge vs. (41) Donald Trump

What a contrast in styles! This matchup pits Coolidge (one of our most restrained presidents) with Donald Trump (who embodies the very absence of restraint). Further, it’s notable that despite William Henry Harrison serving only a month in office, the historians’ survey ranks him above “The Donald”.

Trump did, nevertheless, have a clear vision for America—one built around immigration enforcement and an “America-first” approach to the globalized economy. His administration also acted with some decisiveness in the COVID-19 pandemic, and despite frequent Twitter bombs, he kept America mostly free from embarrassing international incidents. However, he added more to the national debt than any previous president, the Trump White House was a hodge-podge of dysfunction, and he abjectly flunks the “moral authority” test. One could argue that Coolidge set Hoover up to deal with the coming Great Depression—however, I conclude that this is unfair. Contributions to prosperity is a close run, as Trump did preside over three prosperous years during his time in office…but this doesn’t quite top the “Roaring Twenties”.

Final result: Coolidge wins, 5-2.

Lincoln’s Quarter—Round of 32

(1) Abraham Lincoln vs. (33) Rutherford B. Hayes

It’s difficult to make much more than a half-hearted case for Hayes on this one. Lincoln’s time in office is largely defined by his management of the most severe crisis in American history: the Civil War. His vision for America was crystal clear: in favor of a single, united nation. Detailed scholars of the Civil War era will rightly point out that many of Lincoln’s actions as president went well beyond the powers granted to the federal government and the executive branch. Yet Lincoln’s employment of such means was largely devoted to the furthering of American ideals.

Where Lincoln is most vulnerable to criticism is his choice of vice president during his second term—while an electable candidate to woo northern Democrats, Andrew Johnson would be an ill-fitting president in the postwar government. Further, the Civil War was too traumatic an episode for there to be much prosperity, especially in the south (which was legally part of Lincoln’s jurisdiction at the time of his election).

Final result: Lincoln wins, 5-2.

(8) John F. Kennedy vs. (25) Grover Cleveland

Ah…now we enter dangerous waters. 1960 was the first election with televised debates, and Americans promptly elected one of the most handsome men ever to hold the office. Kennedy’s inspiring words (“pay any price…bear any burden…” and “the torch has been passed”) and mysterious assassination further cement him in the American mind as a president who had the right stuff but never got enough of a chance. Whether or not this is true is beyond our ken to determine. For our purposes, we must stick to the criteria.

Kennedy’s firm hand and willingness to give and take bore the U.S. safely through the Cuban missile crisis. This makes up for JFK’s poor handling of the Bay of Pigs invasion regarding the same island. Kennedy’s vision for America was both clear and inspiring, and he presided over an era of tax cuts and prosperity. However, Cleveland will simply not go quietly.

It may be unfair that we compare two presidents from such different times by the same measure, but that is what American ideals and founding principles require us to do. Cleveland pointedly refused to overstep his conception of what were appropriate federal actions, and in so doing, he gains a point over Kennedy for consistency with America’s founding. I’ll readily admit this is controversial, and Kennedy suffers because he served in a far more complex and dangerous time—the Cold War era. Yet so be it.

“First Citizenship” could also go either way. While Cleveland avoided the Civil War draft by paying a substitute to take his place, Kennedy did serve in World War II. Yet Cleveland’s commitment to honesty about his extramarital affair stands in contrast to Kennedy’s coverups of far more numerous infractions.

The final two categories are hardly close. JFK gets penalized for continuing the U.S. military presence in Vietnam, and for selecting Texas’ Lyndon B. Johnson as his vice president. Johnson would go on to preside over the largest expansion of the federal government—and most daring redefinition of America’s purpose—since the New Deal. The result of all this? Our first upset.

Final result: Cleveland wins, 4-3.

(9) Ronald Reagan vs. (24) Calvin Coolidge

While not a sweep, this one doesn’t feel close. We give Reagan credit for his deft diplomacy and statesmanship that contributed toward ending the Cold War—but we also have to recognize that many of his military operations were well beyond the spirit of the Constitution’s executive powers. He was known as the “Great Communicator” and did much to revive conservative thinking in a nation that had spent nearly eight decades trying different forms of progressive policies.

While Coolidge presided over a period of great prosperity, we give Reagan the edge there given the tax cuts, deregulation, and recovery from the economic “malaise” of the 1970s. The final two categories are fairly close; we give Coolidge a point for externalities given that much of the so-called “military adventurism” of the Bush administrations really got its start under Reagan. But this isn’t enough to alter the result. One win for the Gipper.

Final result: Reagan wins, 5-2.

(16) James Madison vs. (17) John Quincy Adams

It’s difficult to criticize much about Madison’s consistency with American ideals, or his contributions outside of the presidency. He is often called the “Father of the Constitution”, and his strand of political thought runs throughout America’s founding documents. As such, it’s also difficult to debunk his vision for America—Madison’s vision for America was in many ways the original vision for the United States under a federal system of government.

As if that wasn’t enough, Madison presided over the War of 1812. Whatever one feels is the principal cause of the war (American territorial ambitions in Canada, oppressive British practices at sea, etc.), it was necessary to go to blows with the British again in order to prove America’s legitimacy as a nation. The United States earned independence in 1783, but did not earn respect until 1815. Because of this, it’s tough to dispute that Madison clearly left office with the country having been better off because of it.

John Quincy Adams gets credit for a few things, however. The trade disputes and embargos leading up to 1812 did much to damage the U.S. economy, while Adams generally avoided such poor economic policies. Further, Adams governed as president while surrounded by a star-studded coalition of Whigs, included the “Great Compromiser”, Kentucky Congressman and perennial not-president Henry Clay.

On the whole, however, this matchup is not as close as the C-Span rankings would suggest.

Final result: Madison wins, 5-2.

Lincoln’s Quarter—Round of 16

(1) Abraham Lincoln vs. (16) James Madison

Here we have some very tough decisions. This is the type of matchup that feels like the final round, and a very difficult test for Honest Abe.

We already mentioned Madison’s record: “Father of the Constitution”, contributor to the Federalist Papers, and commander-in-chief during the War of 1812. I firmly think that Madison’s C-Span ranking does not do his contributions to America justice.

But recall: this is Abraham Lincoln! Madison may have the superior Constitutional bona fides and a more effective/less dissent-ridden cabinet and vice president. But Lincoln’s management of the Civil War was far more skillful at a moment when the utmost was required. His stand for the Union’s ideals was necessary to realize the first step toward racial equality—something Madison gave little attention to. The final nail in the coffin is Lincoln’s avoidance of any foolish peacetime economic policies like Madison’s embargo debacles…simply because Lincoln was practically never a peacetime president.

It’s painful for me to see an underrated founding father bounced so early—but it’s the right move.

Final result: Lincoln wins, 4-3.

(25) Grover Cleveland vs. (9) Ronald Reagan

Fresh off the upset of JFK, Cleveland now faces another 20^th century titan. This time, many of his same weaknesses are too much to overcome.

In his second term (1893-1897) Cleveland witnesses a major financial panic, one which brought political turmoil and labor violence far beyond the 1987 stock market crash on Reagan’s watch. Reagan’s White House included another future president at VP, and the tax cuts and liberalization of the economy contributed greatly to prosperity. Reagan is again vulnerable on some foreign policy points (Iran-Contra, Lebanon, etc.), but it’s not enough to change the outcome.