Tim Keller and the Two Senses of “Winsome”

Tim Keller and the Two Senses of “Winsome” May 11, 2022

Image credit: The Atlantic

Over the last week or so, there’s been something of an online dust-up involving the approach to Christian cultural engagement modeled by Tim Keller—pastor of Redeemer Presbyterian Church in New York City. Keller has long been a favored target of those who would challenge “establishment” American evangelicalism from the right, but in recent weeks he’s been subjected to a level of criticism previously reserved for perceived defectors like Russell Moore.

The current brouhaha began when the ever-interesting James Wood published a thoughtful piece entitled “How I Evolved on Tim Keller” at First Things. Wood’s argument, to be clear, is the farthest thing from incendiary: it renders gentle disagreement with certain aspects of an “elder statesman’s” intellectual trajectory. Specifically, drawing on Aaron Renn’s “three worlds” thesis of patterns in American Christianity, Wood reflects that the “winsome model” of Christian engagement—often associated with Keller—seems increasingly ill-suited to the contemporary moment. Wood points out that “[i]f we assume that winsomeness will gain a favorable hearing, when Christians consistently receive heated pushback, we will be tempted to think our convictions are the problem,” and argues that Keller’s generally apolitical orientation risks “encourag[ing] in its adherents a pietistic impulse to keep one’s hands clean, stay above the fray, and at a distance from imperfect options for addressing complex social and political issues.”

Here’s what I take Wood to be emphasizing, in broad strokes:

  1. There’s no clean line between political convictions—which are typically founded on moral convictions—and theological commitments. Hence, it isn’t wrong for Christians to judge that some political project is more consistent with those commitments than another project, even if those commitments are never fully realized.
  2. The elite secular world is growing increasingly hostile to traditional Christian convictions, in an expanding range of spheres. This will make it much more difficult for “known” Christians to attain positions of mainstream cultural influence without being pressured to compromise their convictions. In many cases, doing so may be impossible.
  3. Those in positions of influence within the Christian community have a responsibility to be clear-eyed about these trends and to help equip their parishioners accordingly.

All of this seems plainly correct to me. And I agree with Wood that sometimes, Keller’s work (in particular his Twitter presence) can come off as somewhat above-it-all, reflecting a perhaps unduly optimistic view of the status quo.

I thought it would end there, until erstwhile conservative commentator David French blasted out a decidedly uncharitable reply entitled “A Critique of Tim Keller Reveals the Moral Devolution of the New Christian Right.” French reduced Wood’s argument to merely a “Great Rationalization,” implicitly charging Wood with merely carrying water for right-wing populism. That analytical frame is extraordinarily shopworn at this point—it is long past time for commentators, French in particular, to stop interpreting every issue through the lens of the 2016 presidential election—but French’s piece nevertheless kicked off a whole new round of online denunciations on all sides.

What to make of it all? I wasn’t originally going to write about this issue, but the more I’ve reflected on it, the more it seems like an important conversation to have—in particular because the word “winsome” was so frequently used at my undergraduate alma mater that it became a punchline. Is it possible to better spell out what is meant by this fraught term?

Etymologically, the word clearly has to do with winning someone over—but how, and for what? Indeed, the word has at least two different senses, which are worth distinguishing: inculturation is not the same thing as courtesy.

By “inculturation,” I mean the sense that Christians today can be respected members of elite secular culture while making few moral compromises, and should aspire to that goal. Hence, “winsome” here would mean that others are won over such that they accept Christians as peers within the same circle or class. It’s that ambition that Wood—and I—would increasingly find dangerous under present conditions.

“Courtesy” is something quite different—a disposition willing to see the image of God in others, to extend kindness even where it is not necessarily reciprocated, and (in discourse) to avoid bad-faith interpretations of an opponent’s arguments. It is not in any sense, however, “unilateral disarmament” when it comes to fighting for truth. “Winsome” in this sense means that the other is won over in that their prior negative perception is at least somewhat destabilized, or that their understanding of their opponents becomes a little more nuanced.

(Note that in the former case, the governing assumption is that the “other” is merely curious; in the latter, the “other” is assumed to be somewhat hostile. This is essentially the “neutral world”/”negative world” distinction that Renn builds out.)

Criticism of winsomeness-as-inculturation should not (and need not) shade over into criticism of winsomeness-as-courtesy, although in practice it often does. It is beneath the dignity of Christians to suggest that those who don’t have bomb-throwing temperaments are, automatically, moral compromisers.

Some years ago, I heard Keller speak at a Veritas Forum event alongside Yale professor Anthony Kronman, on the subject of Kronman’s new book Confessions of a Born-Again Pagan—a lengthy treatise defending a neo-Spinozist religious orientation. The conversation was measured, thoughtful, and respectful, even though both discussants had profound disagreements with one another. It was winsomeness-as-courtesy at its best: Keller wasn’t gunning for a teaching job at Yale, and Kronman wasn’t auditioning for a staff position at Redeemer. And the Church still needs people who can have these kinds of conversations.

I get the sense that some of Keller’s online critics (though certainly not Wood, to be clear) are frustrated as much by his modeling winsomeness-as-courtesy as by any tendencies toward winsomeness-as-inculturation. And that’s a problem, even though it’s not the one French diagnoses.

I’m sure Keller has said things over the years that I wouldn’t want to defend. (I’m sure I’ve said things over the years that I would no longer defend!) But the issues here are very different than those raised by thinkers who insist, say, on applying Foucauldian genealogical critiques to the bulk of the Christian tradition. “Misreading the moment” is not the same thing as a self-conscious campaign to revise longstanding doctrine.

I’ve appreciated Keller’s work for a long time. I don’t agree with everything he’s said in the last few years. But I’m grateful for his ministry nevertheless.

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