Out on a Limb: Selected Writing, 1989-2021, by Andrew Sullivan (Avid Reader Press: 2021), 576 pages.

Few have followed in the footsteps of Andrew Sullivan. As a British-born, unabashed Reagan-Thatcher conservative, he became one of the most clever and subversive writers at a popular left-leaning U.S. political magazine. As an established journalist decades later, he became one of the earliest proponents of internet blogging as an alternative medium. As a gay man, he has often chastised the radical identity politics of his peers, and been rebuffed for doing so. At odds with his Church because of his sexuality, he has remained one of Christianity’s stalwart defenders in the public square. Many have had reason to passionately disagree with him. Almost none disrespect him.

His thoughtful, often contrarian views are now collected in his recently published volume of essays, Out on a Limb: Selected Writing, 1989-2021. The book is a thrilling intellectual romp through the last 30 years of political and cultural debate. It is also about a love for the American idea, and the disappointment only an immigrant can feel when the nation fails to live up to it. To call Sullivan’s writing consistent would be misleading. He is a peculiar kind of conservative. But he is, on second reading, precise in negotiating practical solutions to political disagreement. Because he cares not just about the future of the American project but, ultimately, about the souls of the people he writes about, whether they agree with him or not.

Borrowing from the conservatism of Michael Oakeshott, Sullivan has always put the “radical acceptance of what is,” as he summarizes the British philosopher’s outlook, at the center of his political philosophy—the empirical reality of a society’s customs and beliefs before their ideal formulations. For both, conservatism is not an ideology; it is a disposition. “To be conservative,” Oakeshott wrote in a seminal essay, “is to prefer the familiar to the unknown, to prefer the tried to the untried, fact to mystery, the actual to the possible, the limited to the unbounded, the near to the distant, the sufficient to the superabundant, the convenient to the perfect, present laughter to Utopian bliss.” It embraces tradition, but not uncritically so.

Such conservatism is not the usual mode of discourse in American politics, to say the least. No lawmaker or party official would be worthy of its name. Few voters would find comfort in it. It eschews partisanship and resists favoritism. It is not a “conservatism of faith,” as Sullivan says much of the post-Reagan right has become, preferring clear governing principles grounded in eternal truths about humanity. It is, rather, a “conservatism of doubt,” skeptical about any one faction in a polity being privileged with a better understanding of the good life. It is prone to incremental change. Its watchwords—not often celebrated today—are compromise, coherence, restraint. A conservative like Sullivan who doubts, then, is one who is often reviled, even by those with whom he holds beliefs most in common. The political figure he admires most is a “trimmer,” one who keeps the ship of state on an even keel as it is blown and tossed by the winds of ideological disagreement. “What the conservative is about, in other words,” Sullivan says, “is balance.”

So he writes, for example, with directness about how federal hate crime legislation builds a society of increasing suspicion and mutual recrimination. But he also writes with moderation about the necessity of legalizing civil marriage for gay men and women. He rouses journalists and politicians to a moral clarity about their shameful treatment of Monica Lewinsky, but he kicks himself decades after the Iraq War for his “narrow moralism.” (He elides in the collection his own earlier defense of the war.) He dares to call Barack Obama’s candidacy “necessary,” and, equally daring, he praises Margaret Thatcher as a feminist “liberator,” one who dodged the leveling forces of British leftism. Perhaps most importantly, he argues against the “privatization of faith” that liberalism imposes, and defends great religious figures who “renounce power.” Yet he inveighs against religious fundamentalism in political rhetoric.

For this reason, conservatives have often looked askance at Sullivan, just as he has looked askance at them. More than a few of the essays are takedowns of the Gingrich-led Republican Revolution, which he dismisses as “inherently pessimistic.” During the Bush presidency too, he argues conservatives lost their emphasis on economic freedom, limited government, and personal responsibility, choosing instead to put their faith in the outcome of two dubious wars: a war on terror abroad and a statist war on progressive culture at home. Conservatives have good reason to quibble with these characterizations. They are overly broad. And if conservatism is really about restraint, as Sullivan says, shouldn’t restraint apply to laws that would edge out traditional morality? Is a man who revels in the “sexual energy” of Princess Diana or gay bacchanalia truly conservative? There appears no limiting principle to his political philosophy, just a guarded incrementalism, a continual march toward increasingly worse compromise.

The difficulty of Sullivan’s conservatism is that it holds the importance of societal pluralism and political assimilation in tension. America’s greatness, he says, is its ability to integrate disparate people around universal freedoms. But equally, he says, it is our “talent for contradiction,” our truly classless exchange of ideas, that makes us great. It is what gives us the “primary colors” of our national spirit, from Hamilton to hip-hop. And it’s what gives us Sullivan’s own ideas about conservatism being the best check on unbridled liberalism; about civility being as important as good lawmaking; about the dangers of using opposing extremisms to justify a more radical politics; about the horrors of torture; and about the mobocratic tendencies of journalists in legacy newsrooms.

Yes, Sullivan can be a gadfly. But he is one who chastens conservatives and liberals to better versions of themselves. It’s something he’s able to do because he believes a healthy polity rests on a bedrock of religious morality. He cautions Christians against placing their faith in politics because he knows societies must rely on more than political arguments to flourish. Above all, he is a writer in the tradition of Samuel Johnson, bringing all available faculties—intellectual, emotional, moral, and spiritual—to bear in his work.

If current trends are any indication, his will continue to be a path rarely taken. The left defenestrated him last summer. He was fired from New York magazine, abruptly and somewhat preemptively, for, in his words, not being “actively committed to critical theory in questions of race, gender, sexual orientation, and gender identity;” in other words, for not being an ideologue. (The New York Times issued its parting shot against him shortly after, when their media critic visited Sullivan at his home on Cape Cod to try to make him apologize for publishing excerpts of The Bell Curve in the 1990s.) And he has already departed from the right. Embracing disagreement for so many years may have generated his most influential writing, but it has politically isolated him. For the time being, his is a footloose tribe. Follow him if you dare.

Josh Christenson is an assistant editor for the Washington Free Beacon.