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The Official Presidential What-If Tier List

A look at some of the many would-be candidates and leaders the country nearly had in advance of the latest most important election of our lifetimes.

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ettingermentum
Aug 25, 2026
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As hard as it may be to believe, it is true: the 2028 presidential election cycle will begin in earnest less than three months from now. As things stand, we are a long way from knowing how this race will go, who it will be contested between, or even what its most important issues will be. But there are two things that we can say with absolute certainty: a) that it will be framed in absolutely existential terms, and b) that voters will regard it as such. Despite the deep and chronic unpopularity of both major parties, the historically consistent unpopularity of major party candidates, and widespread disillusionment in the fairness and legitimacy of the very foundations of American society, recent presidential elections have been characterized by record-high turnout and record-low third party vote shares. The fight for the White House, it seems, has become one of the last places where the public sees any room for contingency, feels any agency, and thinks that anything truly meaningful is happening at all.

It’s not hard to see where they get the idea from. Since the year 2000, all of America’s presidents but one have been either elected or re-elected by small margins across a small number of state(s). The sole exception—Barack Obama—only narrowly won his party’s nomination. The reality that every one of our recent leaders were all only a few bad breaks away from never coming to power at all has loomed extremely large in our collective consciousness, especially so for those to the left of center. After having come out on the losing side of a brutal four of the five ultra-close races of this century, liberal voters have built an entire folk history about the importance of close presidential elections, which they have come to see as the casual factors behind essentially every negative occurrence in American history. Simply replace Richard Nixon with Robert Kennedy, Ronald Reagan with Jimmy Carter, George W. Bush with Al Gore and Donald Trump with Hillary Clinton, it is said, and you solve all of modern America’s problems, from the fascists to the wars to an entire half-century of stagnant wages and rapidly-growing inequality.

How much of this is true? How much isn’t? These are the questions that this article will seek to answer, as the actual implications of the country’s leading alternative history scenarios have gone largely unexamined despite how massively important they are to modern American political culture. Going all the way from Abraham Lincoln’s running mate choices in 1864 to the many opportunities Democrats had to defeat Donald Trump over the past decade, we will look at the most famous examples of would-be presidents and judge them based on how much they could have truly improved things if just a little more broke their way. In doing so, we will follow a brief set of ground rules:

  • We will consider would-be general election winners, would-be presidential successors, and would-be major party nominees. Those in the final category will be at something of a disadvantage, as we will not work off of the presumption that they would have won the general election if nominated. Most in this category rank low for this reason, but some of the most interesting are at the top.

  • With the exception of what-ifs involving elections well before the emergence of the modern party system, this list will consist exclusively of potential Democratic presidents and party nominees. Although there is no shortage of fascinating alternative history scenarios involving conservative Republican politicians, they all either result in things becoming outright worse or only improving in incredibly tenuous and indirect ways. Perhaps one day they can be reviewed in a list about the biggest dodged bullets in American history.

  • Since this is meant to be an exploration of modern liberal historical mythology, most of the cases we will review will be recent—i.e., within the past 50 years. This, however, is not at all a hard rule. Make no mistake: there will be a Benjamin Butler section.

To see what the verdict is for Ted Kennedy, Henry Wallace, Al Gore, Bernie Sanders and many more, read on.

F Tier

Hillary Clinton 2016

Hillary Clinton arriving on stage at the AIPAC Policy Conference in Washington, D.C., 2016

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