Political Philosophy

In Search of Virtù

February 10, 2021

Carson Holloway

Washington Fellow

A few years ago, seeking to understand Donald Trump’s remarkable triumph, I wrote a short article examining his Machiavellian virtues as a political leader. Now, in the wake of his defeat, it is equally instructive to attempt a Machiavellian account of the defects that may have prevented his continued success. To be clear, I am here interested not in any errors Trump may have made after the 2020 election, but errors he made earlier, which prevented him from making a stronger showing in the election.

This undertaking encounters an immediate objection: why should conservatives use Machiavelli’s teaching as a tool for understanding and guiding our politics? After all, most American conservatives believe in the reality of, and the binding quality of, moral principles in a way that Machiavelli clearly rejected. We want our rulers to be guided by sound moral principles, but Machiavelli famously taught that no successful ruler can be consistently “good” and hope to succeed. 

The proper response to this challenge is that anyone who wants to understand politics—as well as anyone who wants to succeed in politics—has to be able to think like Machiavelli. His account of the often harsh realities of political life is too accurate to be safely ignored. This is not to say that conservatives should simply become Machiavellians—amoral seekers of political power for its own sake. It is to say that any effort to guide political life by sound moral principles will fail if it does not also take into account the reality of power politics.

Our greatest statesmen have understood this well. Contemporary conservatives tend to revere Abraham Lincoln. If they would attend closely to his career, they would see that he never made any important decision without considering both the principled basis for his actions as well as the implications for his own power, that of his party, and that of his country. Lincoln was not a political prophet (unlike, say Frederick Douglass) but a practical statesman who knew that he would need to succeed in winning and holding power if he were to do any good for his country as a politician. 

What, then, are the Machiavellian virtues that permitted Trump to succeed to the extent that he did? Machiavelli teaches that humans are primarily self-interested beings. Where many conservative candidates had failed by offering appeals to abstract principles that are of little interest to ordinary voters, Trump succeeded by offering a straightforward and unashamed appeal to the self-interest of Americans.  While Trump’s universally-known slogan issued a call to “Make America Great Again,” his build-up to that slogan in his stump speech always included a promise to “make America wealthy again.”  Trump followed through on this pledge by cutting taxes, cutting regulations, and reconfiguring American trade policy with a view to promoting American manufacturing.  The economic result: better GDP growth and rising wages for the working class.  The political result: Trump won many millions more votes in 2020 than he had in 2016.

Trump also understood or intuited Machiavelli’s observation that in every political community human nature expresses itself in two “humors”: the people and the great. Trump the populist grasped that, as Machiavelli admonished, it is better to found one’s power on the people than on the great, because the former are more numerous and less demanding than the latter. The people mainly want to be left alone and have their essential interests respected, where the great cause trouble because they are ambitious to rule and want to impose their wills on the people. By understanding this Trump was able, with not much difficulty, to take over the Republican Party over the strenuous objections of its wealthy donors and their preferred leaders. 

Finally, Trump understood with Machiavelli that republican self-government tends to foster both an ardent love of country and a spirited self-respect in ordinary citizens. Hence Trump’s routine appeals to the patriotism of his voters, as well as to their resentment at having been disdained by their own ruling class. These themes provided an emotional energy to Trump’s movement without which a mere appeal to self-interest would probably have been insufficient to deliver victory in 2016.

Trump’s Machiavellian astuteness carried him through many storms. By his attention to the self-interest, self-respect, and patriotism of his voters, he forged for himself a loyal political following that supported him through the two nerve-wracking years of the (spurious) Mueller investigation and earned his party a satisfactory (although not ideal) outcome in the 2018 elections. Trump’s base likewise sustained him through an impeachment in the final year of his presidency and made his 2020 campaign competitive even though he was opposed by many of the nation’s most powerful and wealthy interests. In sum, Trump’s understanding of and loyalty to his “people” permitted him to face down and almost defeat most of “the great” in league against him. 

Almost—but not quite. Why, then, did Trump’s Machiavellianism fail him? 

We might at first be tempted to conclude that Trump was defeated through no failing of his own but was instead overpowered by forces beyond all human control. Machiavelli himself suggests that such things can happen. Perhaps Trump is like Cesare Borgia, as described in Chapter 7 of The Prince: a man who carefully laid the foundations of present and future power through his bold and spirited actions, but who was in the end undone by an extreme malignity of fortune. Perhaps Trump was similarly bested by bad luck in the form of the COVID pandemic and the novel election practices that it allowed in certain states that would have been necessary to his victory. 

Although this account might be attractive, especially to Trump’s most ardent fans, Machiavelli’s presentation of Cesare Borgia calls us to a more searching inquiry. For by the end of Chapter 7, Machiavelli reveals that Cesare, although assailed by an extreme malignity of fortune, had also made errors that, combined with bad luck, led to his downfall. Cesare misunderstood an essential element of human nature: he foolishly believed that great ones will forget past offenses, and so he faced a determined enemy where he expected to find a much-needed ally.

Similarly, Trump may have erred by drifting to some extent from his original Machiavellian position. He neglected his strongest ground: the people versus the great. Trump energetically denounced the Democrats as socialists and even communists when it would have been better to lead the people against the establishment once again. There was good material here. After all, the COVID response in many states has enriched large corporations while decimating small businesses. 

Moreover, Trump’s 2020 campaign may not have been sufficiently positive and future-oriented to appeal to the self-interest of voters. Machiavelli teaches us that human acquisitiveness is insatiable. A successful politician, then, must not only remind the people of the good things he has provided in the past (which they will tend, selfishly, to forget), but also of the good things that he will provide in the future. Trump, then, may have made a misstep by relying too much on a negative critique of Joe Biden. This is an understandable error, since Biden’s manifold weaknesses invited a negative campaign. But Trump had won in 2016 not only by trashing the country’s political establishment but also by promising something new and better. 

If these were mistakes, they were probably not deadly ones. On a Machiavellian account, Trump’s most fundamental and destructive (to him) error was his failure to sufficiently respect the appearance of morality that political life demands—and here I must acknowledge that Catherine Zuckert noted this defect in Trump in a critique of my original article. According to Machiavelli, although the prince cannot be good consistently, he must consistently appear to be good, because the people demand it, and the people are the wise prince’s base of power. Machiavelli famously admonishes in chapter 18 of The Prince that a leader should take care that he always appear “altogether merciful, faithful, humane, upright, and religious.” 

Supporters of a Trumpist right need to face the reality that the American people—and especially the ones who turn the scales in national elections—have a gentleness of spirit that precludes supporting a leader who is too verbally pugnacious. 

Here we need to be precise. Trump did not entirely neglect this essential Machiavellian precept. He routinely presented his positions in moral terms. Nothing is more common than for Trump to claim that we “have to do the right thing,” or to present the actions of his rivals as a “disgrace.” Indeed, in some important ways Trump was superior to past Republicans on this very point.  It had become routine over the last two or three decades for national Republican leaders—think of Bob Dole, George W. Bush, John McCain, and Mitt Romney—to acknowledge the moral legitimacy of most of the left’s demands while offering less ambitious proposals in pursuit of the same ends.  In contrast, Trump never conceded the moral high ground to Democrats, which is wise, both because it is disadvantageous to do so and because they don’t deserve it.

But Trump overlooked something important, about which both his friends and enemies constantly reminded him: the need to be nice, or the need to at least appear to be nice. Americans on the whole are a gentle and easygoing people. They want a certain toughness in the president, of course, but they also want him to be restrained, to be likable, to be kindly. Trump is actually capable of projecting these qualities, no doubt because he actually possesses them. Anyone who has seen him with the victims of a natural disaster, or at an event honoring aged veterans, has seen how solicitous he can be.

Trump, however, seems to have wanted to present the kindlier side of his character only on his own terms—reserving the right to be as brutal as possible with his enemies. The trouble is not that he would retaliate rhetorically on his enemies. No doubt the necessities of Machiavellian politics require such displays of strength and willingness to fight. The trouble is that his retaliations were often personally abusive in a way that many voters think is not appropriate to the presidency. There is nothing wrong with Trump calling James Comey a “liar and a leaker.” That is just telling the truth. But to use Twitter, for example, to comment on Mika Brzezinksi’s personal appearance is too much for most Americans. 

Here we encounter a strange paradox in Trump’s approach to American politics. Trump is sincerely patriotic and he made a point of continually reminding Americans of the need to show reverence for their country, to not let it be a “laughingstock” in the face of the world. It somehow escaped him that many voters would agree with him on this, and for that very reason be put off by his determination to retain and display his brawling persona even while occupying the country’s highest office. 

Here we also encounter a certain flaw in Trump’s character, understood from a Machiavellian point of view. Trump is too proud to be a complete Machiavellian. He has a certain sense of honor and disdains to appear to be other that what he is. This is in one sense a source of great Machiavellian strength. The Florentine warns that princes must not be light and changeable, and Trump’s honorable determination to be loyal to his own voters was essential to his political success. Nevertheless, it is central to a Machiavellian populism that the prince attend to appearances: the people expect you to appear to be moral in a way they can recognize and approve, and the prince has to accommodate that expectation. 

Machiavelli is famous as a teacher of political realism, and his teaching is indispensable even for those who are not themselves Machiavellians. To have any hope of making things better, we have to face them as they are. Traditional Republicans and old-school conservatives have to face the fact that their technocratic policy prescriptions have little appeal to the self-interest or self-respect of contemporary voters. Supporters of a Trumpist right need to face the reality that the American people—and especially the ones who turn the scales in national elections—have a gentleness of spirit that precludes supporting a leader who is too verbally pugnacious. 

These reflections point the way forward for the American right. To borrow the famous language of George H.W. Bush, that way requires a “kinder, gentler” Trumpism—one that appeals to the self-interst, patriotism, and self-respect of ordinary Americans, but without descending to a personal abusiveness that most Americans cannot stomach. This path, and the chances of success that it holds out, awaits whatever politician of the right has the Machiavellian astuteness to follow it.

Originally published by Law & Liberty.