The Art of Losing
Updated: Jun 20
This article originally appeared in The Millennial Review
Among the legions of hilariously audacious promises Trump made during the 2016 elections came the assurance we’d be winning so much we’d “get so tired of winning.”
Now, what ordinarily follows an opening line like the one above is an emphatic statement from Trump supporters that he’s accomplished more than anyone since FDR or from Trump opponents that he’s passed no major legislation while squandering whatever political capital he had on useless Tweeter wars. And each side would come armed with an exhausting list of examples to support their claim. But I’d like to do something different; I’d like to focus not so much on the question of whether we’re “winning” but ask what “winning” means, and whether—perhaps you should sit down for this—whether winning is the most important thing we could be focused on?
As we saw in early September with Trump acquiescing to Pelosi and Schumer’s debt ceiling deal—in spite of the fact he was holding all of the cards—when “winning” has no discernible purpose or direction, it can look an awful lot like losing. It’s easy to “win” when the definition of winning is altered each time an obstacle is encountered. But the first rule of progress is that we must be progressing towards something rooted in more than the ever-changing fickle mood of popular sentiment. To quote G. K. Chesterton: “As long as the vision of heaven is always changing, the vision of earth will be exactly the same. No ideal will remain long enough to be realized, or even partly realized. The modern young man will never change his environment; for he will always change his mind. This, therefore, is our first requirement about the ideal towards which progress is directed; it must be fixed.” Unless and until we can agree on what the heck Make America Great Again! actually means, we might as well be shouting Change You Can Believe In!
And therein lies the problem: when your core principle is winning, you tend to support winning over core principles. The emotional appeal of feeling like a winner outweighs the wisdom in considering the long-term implications of an immediate win. There’s a worrisome shortsightedness to the sort of winning Trumplicans advocate that may jeopardize whatever temporary gains have been made. Sure, we can screw Ryan and McConnell and all those “establishment” Republicans who are supposedly standing in the president’s way; but when we have to side with Pelosi and Schumer to do it, what have we accomplished?
It would behoove those who recently lost heart with the conservative movement because it’s supposedly no longer “winning” to re-examine our history. Edmund Burke, the father of modern conservatism, bemoaned a world descending into radical revolution in the eighteenth century. Russell Kirk penned his famous 1953 masterpiece, The Conservative Mind, as a sort of obituary to the conservative movement. Barry Goldwater, the first modern “conservative” candidate for president, suffered one of the most lopsided defeats in American history in the 1964 election. That same year, Ronald Reagan’s efforts to support Goldwater in his famous “Rendezvous with Destiny” speech was likewise a failure. A decade later Reagan was again rejected in the 1976 presidential primaries. The following day he told his campaign staff, “Sure there’s a disappointment in what happened; but the cause goes on.” He could say that because Reagan’s message was about the cause, not Reagan.
And yet, these men ultimately accomplished far more in defeat than most have in indiscriminate victory. It was because of their tireless efforts in the face of defeat that the conservative movement didn’t perish. None of them determined that—having faced defeat and bitter rejection—they’d just as soon abandon their principles and adapt a view that was more favorable to the constantly changing whims of the masses. Political loses, setbacks, and failures are not necessarily a sign of weakness or impractical purity. Losing is the default position in politics; winning is rare, and winning without suffering heavy losses in the process is miraculous.
Economist and Nobel laureate Milton Friedman said of Ronald Reagan that he, “was the first president in my lifetime who was elected not because he was saying what the people wanted to hear but because the people had come around to wanting to hear what he was saying. He said the same thing in 1980 that he had said in 1964 in supporting Goldwater. He could not have been elected in 1964, and he was elected in 1980.” The reverence shown Reagan in the Republican party borders on the absurd—not because he is particularly undeserving, but because so many have claimed him as their political role model while advocating policies or tactics that he largely disapproved. It’s easier to advocate the idea of Reagan the victor than Reagan the conservative. That is, it’s easier to support someone who’s a “winner”—whatever that may mean—than someone who is advocating a specific worldview, regardless of how popular those views happen to be.
None of this suggests that it is appropriate to hold to such political purity as to be a martyr in every fight. Wisdom decrees that we are to use discernment in choosing our battles and determining which hills are worth dying on or when compromise is warranted. The so-called “Eleventh Commandment”—Thou shalt not speak ill of any fellow Republican—has been attributed to Reagan to illustrate that he well understood there are times when political purism stands in the way of the cause, just as there are times when a lack of principles stands in the way.
Libertarians and classical liberals may lose heart staring into the abyss of popular sentiment growing against the principles of liberty and limited government. But the conservative trusts in Providence. That is, the conservative does not take it upon himself to “save humanity” but trusts that a Higher Power has ordained what shall be. The conservative’s charge is to act with integrity and wisdom and to leave it to Providence to determine the ultimate fate of the civilized world. The conservative isn’t looking for a miniature messiah in the form of a political savior—as Trump has come to represent for so many—but a transcendent Messiah, irrespective of who happens to be in power.
Perhaps at this point you’re growing uncomfortable because I’m getting religious; but that is precisely the point. As British philosopher Roger Scruton observed in his book, How to be a Conservative, “The loss of religion makes real loss more difficult to bear; hence people begin to flee from loss, to make light of it, or to expel from themselves the feelings that make it inevitable.” One does not have to be pious to understand that the absence of religion from society leaves men vulnerable to a nihilism that reduces life’s pursuits to “fun” and “winning”. Scruton continues, “The Western response to loss is not to turn your back on the world. It is to bear each loss as a loss. The Christian religion enables us to do this, not because it promises to offset our losses with some compensating gain, but because it sees them as sacrifices. That which is lost is thereby consecrated to something higher than itself.”
Even non-religious conservatives such as Matthew Arnold and John Ruskin recognized there was much at stake with the loss of Christian culture in the West. And the conservative movement has traditionally held that our religious heritage is a sacred inheritance worth preserving for more than nostalgia’s sake. An inability to stand on principle and take a loss is itself a sacred loss greater than whatever a temporal victory may bring. An overemphasis on “winning” is an indication that we’ve lost the soul as people place their identity in the misery of a political tribe.
“I am a conservative. Quite possibly I am on the losing side; often I think so,” wrote Russell Kirk several generations ago, “Yet, out of a curious perversity I had rather lose with Socrates, let us say, than win with Lenin.” Can Millennial conservatives muster the strength of mind to say the same today? Once again, a new generation of conservatives faces the very real possibility of the movement fading into oblivion. The only thing that has prevented that in the past were those brave men and women willing to choose the prospect of losing over meaningless victory. Let us pray that we can find the same courage. Because when all we’re about is winning, we’ve already lost.