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Reviewed by Michael McDonald

Outside Looking In:
Adventures of an Observer

by Garry Wills

Do the words “The Wills Watch” mean anything to you? If you’re a conservative of a certain age whose political views were shaped by reading William F. Buckley, Jr.’s National Review in the 1970s, I’m sure they will. The “Wills” in question is Garry Wills, the prolific journalist, critic, and historian who, apart from scientific matters, seems to specialize in just about everything under the sun—while devoting particular attention to American politics and history, Roman Catholicism, and Classical antiquity.

Wills began his writing career at National Review in 1957, thanks to Buckley. “But,” as Wills writes in his new memoir, Outside Looking In, “the convulsions of the 1960s and their aftermath tore many people apart, and they did that with us.”1 That is to say, in a twelve year period Wills grew increasingly estranged from the kind of conservatism espoused in the pages of National Review and moved from right to left on the contentious issues then roiling American society: principally civil rights and the Vietnam War. By the end of the 1960s, estrangement had led to irreconcilable differences; Wills and Buckley parted ways.

Sadly, the separation was not amicable. Enter “The Wills Watch,” a recurring feature of the magazine, which was usually written by the late Joseph Sobran. (Ironically, Sobran would himself be forced out of National Review many years later, in the wake of columns of his that Buckley deemed to be “contextually anti-Semitic.”) “The Wills Watch” existed to chronicle Wills’s post–National Review activities in service to American liberalism.

Wills had long since departed from National Review when I (to indulge in a bit of memoir writing of my own) began subscribing in the malaise- and stagflation-ridden Age of Carter. It was, however, through “The Wills Watch” that I not only became aware of Wills’s previous association with the magazine, but also became curious about the reasons for his apostasy. The first book by Wills that I read was Confessions of a Conservative, when it came out in 1979. I disagreed with much of the political philosophy that it espoused, but was captivated by its first third, in which Wills vividly recounted what it was like to work at National Review with Buckley, Frank Meyer, Willmoore Kendall, William Rusher, and other important figures from the magazine’s early years.

From Confessions of a Conservative, I went on to several of Wills’s earlier books: Chesterton (1961), Nixon Agonistes (1970), Bare Ruined Choirs (1972) and Inventing America (1978). My reaction, in each instance, was quite similar: great admiration for individual passages of bravura writing that were overshadowed by serious reservations as to the larger political, historical, or religious arguments being made, especially on such matters as the meaning of “true conservatism.” And yet when all was said and done, there could be no doubt: a habit had taken hold. I had become a “Wills watcher” for life.

In the pages of National Review, “Wills watching” was generally conducted with a light touch: a regretful skewering of a formidably gifted former colleague who had inexplicably changed sides. Indeed, properly viewed, these barbed rebukes were nothing if not backhanded tributes to the intellectual contributions that Wills had made to the conservative movement before taking leave of his senses to embrace radical chic. Yet, at times, it morphed into Wills bashing. For example, one issue of the magazine dedicated an entire cover to a doctored photo, in which Wills’s head was superimposed upon a shotgun- and spear-wielding image of Black Panther Party founder Huey Newton.

It behooves me, then, to be clear about what I mean by “Wills watching”—especially because Wills himself is a self-described “wordaholic.” Thus, for example, in his new book, Wills castigates Buckley for having “poisoned the general currency” of the word “oxymoron.” Buckley, per Wills, thought it was a fancier word for “contradiction” and, as a result, legions of conservatives are now wont to say, as Buckley first did, that an “intelligent liberal is an oxymoron.” But Wills observes that the Greek word means something quite different: something that is surprisingly true, a paradox, a “shrewd dumbness.” Point taken: definitional precision matters.

There are two aspects to being a Wills watcher: the first is to be an avid Wills reader, no mean feat given the man’s Stakhanovite output. Wills regularly writes and reviews for many newspapers and magazines, foremost among them The New York Times and The New York Review of Books. In addition, he wrote, by my count, no fewer than forty-two books between 1960 and 2010. The second and less passive aspect of Wills watching consists of an alertness to the various ways—some less subtle than others— in which Wills himself takes his own peculiar liberties with words, as he chronicles his activities, his political allegiances, and, of course, the underlying “conservative” philosophy exemplified by those activities and allegiances.

Outside Looking In seems principally intended to provide an overview of the main political incidents in Wills’s life, as well as a distillation of many of the people and issues upon whom and which he has trained his gimlet eye throughout his career. There is an “executive summary” or “greatest hits” feel to the book. Veteran Wills watchers will recognize many of the anecdotes he recounts—anecdotes that he previously described with greater feeling in earlier books and essays. But if you’re new to Wills watching, Outside Looking In is a good place to begin. All the more so since the book also offers numerous opportunities to move from the passive to the active part of Wills watching—which is where the real pleasure is to be had.

The opening chapter of Outside Looking In sets the tone for the whole. Titled “Reading Greek in Jail,” it juxtaposes Wills the scholar with Wills the activist. The time is 1968. The place is the Democratic convention in Chicago—“a swirl of action,” of protesting, tear gas, and arrests. Wills is hesitant to take sides just then. But four years later, in 1972, “events catch up” with him, and he’s involved in protests that lead to his arrest. Wills reads the Greek New Testament while incarcerated and tells his surprised cellmates that “learning Greek is the most economical intellectual investment one can make”: it opens the door to the entire Western philosophical tradition. In short order he describes helping others (including Karl Hess, a former Goldwater speechwriter turned reclusive anarchist, and the radical journalist I. F. Stone) in their attempts to master its complexities.

In the following chapter, “They’ve Killed Dr. King,” Wills relives what it was like to report on the aftermath of the assassination of Martin Luther King, Jr., and his impressions of civil rights leaders such as Jesse Jackson and Andrew Young. In the next, he unexpectedly finds himself in a strip club in Dallas, as a reporter for Esquire magazine, trying to uncover what may have motivated Jack Ruby to murder Lee Harvey Oswald.

The chapters move swiftly. We follow Wills interviewing both the inventor of Mace and Pentagon brass on how the National Guard intended to control inner-city rioting. A subsequent chapter recounts his years in Baltimore, when he served on an educational board with Thomas D’Alesandro III, the city’s mayor and Nancy Pelosi’s brother, and got to know local luminaries such as the “underground” filmmaker John Waters. He delves into his love of movies and opera and the celebrities in both worlds whom he came to befriend (such as Paul Schrader and Beverly Sills). He describes his impressions of various presidents: Nixon “was not the cartoon figure of liberal myth” but rather “an intellectually serious and prepared candidate”; George H. W. Bush, however, seemed “devoid of personal reading memories.” Wills seems most impressed with Jimmy Carter, in large part because of Why Not the Best?, a campaign book that Carter had written that “had a precision that comes from clear thinking.”

He makes some fairly prosaic observations along the way: for example, “Books can open doors,” and “Discussions with conspiracy theorists [here in reference to Oliver Stone] are a waste of time.” But a few aren’t so bland. One of my favorites concerns how ex-politicians make for bad academics. Why? Because they don’t know what to do when their stock of anecdotes runs out: “Politicians live for contact with people. They lose the gift for contemplation, or research, or simple reading. Being alone with a book is a way to die for many of them.”

Wills devotes the four final chapters of the book to more detailed renderings of the four figures in his life who seem to have been most important to him: his father, Jack; his great friend Studs Terkel; Bill Buckley; and his wife Natalie. Wills did not have a particularly close relationship with his father, who is described as a boxer, gambler, failed businessman, adulterer, and racist who never read a book in his life. Yet Jack had “an infectious sense of fun.” For that reason, while Wills the younger believes that though there isn’t much of his father in him, he wouldn’t want to remove what little there is. Wills’s admiration for Terkel stems from Terkel’s sympathy for the common man. Wills describes “the Terkel talent for instant connection with people,” and says that he would have been ideally suited to conduct peace talks in the Middle East.

Buckley, in Wills’s charming portrait, is “one of Wodehouse’s blithe young men—Psmith, say, or Piccadilly Jim—who act forever on impulse.” A born risk-taker, he was “hour by hour, day by day . . . just an exciting person to be around.” Wills extols Buckley’s generosity to family and friends and, along the way, punctures the myths that grew up about him, which depicted him as a social, intellectual, and/or ideological snob. And he wonderfully reveals a secret side of Buckley, “his least plausible identity, that of a working stiff”: in fact, Buckley never had nearly as much money as was commonly supposed, and he had to work hard and tirelessly to adopt his chosen lifestyle. Though it took over three decades, Wills and Buckley reconciled and resumed their friendship in 2005, thanks to Buckley’s sister Priscilla.

Most of the good things that happened in Wills’s life resulted from books. In the memoir’s last chapter, Wills recounts how books— and in part the ruse of a lost book—led him to meet his wife, Natalie, and then to their subsequent intellectual partnership in fifty years of married life.

The best biographers are able to move beyond the masks their subjects present to find what Leon Edel has called the “figure under the carpet” or “life myth,” the “inner myth we all create in order to live.” A good biographer considers not simply the facts of a life but also how his subject wanted to be perceived. The concluding chapters of Outside Looking In demonstrate Wills’s surefooted talent as a biographer. Unfortunately, he is less successful as an autobiographer or memoir writer. Perhaps this is because— as La Rochefoucauld says—it’s easy to see through other people, but we have a harder time seeing through ourselves. Coming to grips with his own “life myth” seems beyond him.

Wills’s title is revealing: Wills wants to be perceived as an “outsider” and a mere “observer.” Why does Wills think of himself as an outsider? First, because of his family: “Neither of my parents went to college or read books”; they also felt that his reading was “abnormal.” He adds that his penchant for reading further cements his position as an outsider: “Reading has made me not so much a participant in life around me as an observer. I have stood to the side of events.” Finally, Wills portrays himself as an outsider because he thinks that he is not easily categorized. He maintains that he stands between the liberal and conservative poles, as shown by his presence on two very different enemies lists: Nixon’s and Alger Hiss’s. Furthermore, whereas liberals are secularists, he is a Catholic. Similarly, he is viewed as a journalist in the academy and as an academic by journalists.

But isn’t an “outsider”—to be definitionally precise again—a person who is isolated from and does not fit into conventional society? Such a definition more than applies to a writer and intellectual such as George Orwell, but not Garry Wills, who is the very model of an insider, and specifically an honored member of the liberal establishment. Consider the evidence. Even during his National Review years he sailed not only with Buckley, but also, as he takes care to point out, with John Kenneth Galbraith and Walter Cronkite. Buckley also helped Wills in the search for a scholarship which took him to Yale, where he studied under the eminent classical scholar Bernard Knox.

The evidence of his insider status following his break with Buckley is still more impressive. Important civil rights leaders, such as Jesse Jackson, asked him to ghostwrite their memoirs. He offers a celebrity list of protesters with whom he has marched: Gloria Steinem, Marlo Thomas, Bella Abzug, John Conyers, Judy Collins, Richard Avedon, and the Berrigan brothers, to name but a few. He casually mentions writing a speech on Jefferson for Sargent Shriver to deliver in France. He has received many honorary degrees. He writes for the leading liberal establishment journals. A party celebrating the publication of one of his books was held at Sardi’s in New York. He received a National Humanities Medal from President Clinton.

In the 1970s, along with Lillian Hellman, Hannah Arendt, and Robert Silvers, Wills was invited to attend a private conference exploring the possibility of impeaching Nixon. In 2009, President Obama invited him and a few other select historians to dinner at the White House, at which Wills advised him to pull out of Afghanistan. Like Byron’s Childe Harold, Wills would have us believe that he “stood among them, but not of them; in a shroud of thoughts which were not their thoughts.” This is, frankly, incredible. Wills stood among “them”—the “them” being the legion of liberal activists, politicians, intellectuals, and academics he has associated himself with since leaving National Review—precisely because the shroud of their thoughts, on most divisive political issues, so neatly enfolds his own.

As Wills himself notes, he was associated with the New Journalism, a style of writing marked by advocacy and activism. Esquire claimed credit for inventing the style, in which journalists apply the subjective techniques of fiction to reporting on current events. As befits a New Journalist, Wills was not an unblinking observer who merely allowed stories to tell themselves. Instead, like his hero Terkel (whose oral histories shape their narrative to conform to Marxist ideology), Wills is a man of the political left. He can hardly be compared to Christopher Isherwood, who, in Goodbye to Berlin, purported to be “a camera with its shutter open, quite passive, not thinking.” The shutter of Wills’s reportorial camera is always open, but is never passive, particularly when it comes to devising ways to advance political liberalism.

Wills’s embrace of liberalism is further revealed in his enthusiasms; “The country is full of people who stood a little taller in their youth because of Jesse Jackson [and his chant ‘I am—somebody!’].” One doubts that Jackson has read many books, but Wills’s disdain for those who read little is nowhere evident here. Wills also praises Terkel for his ability to “size up phonies or ideologues, the greedy and selfish politicians.” Perhaps Terkel had such a talent, though he was only too happy to provide a blurb for the memoirs of the former Weatherman William “I don’t regret setting bombs” Ayers. (“As sensitive and gifted a chronicler,” Terkel piously proclaimed, “as he is a teacher.”) In any case, Wills doesn’t possess it. That is evident from his admiration for Hillary Clinton: “I came to know her fairly well and to like her a lot. She has a wonderful sense of humor. . . . She is a sincere practitioner of religion. And she was also humble.” Someone good at sizing up phonies might note that Hillary could speak self-righteously of “the politics of meaning,” while also making a quick $100,000 in cattle futures. She also didn’t hesitate to back Dick Morris’s (sleazily unprincipled, if ultimately successful) triangulation strategy, with the goal of securing a second term for her husband. But Wills is oblivious to the questions justifiably raised about Hillary’s character. She tells him one day that her favorite book is The Brothers Karamazov (“it opened ranges of spirituality I never dreamed of”), and Wills all but swoons.

Another theme that Wills stresses in the book concerns his bona fides as “an average guy.” Thus he was a fan of Johnny Unitas and the Baltimore Colts when he lived in Baltimore in the 1960s and 1970s. He boasts that he leads a traditionalist life, never having tried marijuana or even tobacco. “I have mainly been a conventional person, a churchgoer . . . saying the rosary every day.” “I have also been incurably square, middle-class, never bohemian. I remain old-fashioned.” In a concession to the reigning tell-it-all climate prevailing in book publishing, Wills further volunteers that his wife is “the only person with whom I have ever had sex.”

I was surprised to read Wills’s avowal of being a churchgoer who’d believe in the Catholic Church even if God didn’t exist. In this respect he reminds me of a character from Brian Moore’s 1972 novel Catholics, the abbot of an Irish monastery who stalwartly defends the passionate traditionalism of his monks and holds the mass in Latin. The abbot vigorously prefers his monks to the post–Vatican II Church that, in his view, has capitulated to secularism—even though he himself doesn’t believe in God.

Wills has translated the Latin satirist Martial and is surely familiar with this famous line of his: “lasciva est nobis pagina, vita proba” (“my writing may be naughty, but my life is pure”). Wills seems to be saying something similar: “My writing may be liberal, but my life is traditional,” implying that in some sense he’s really a conservative. Unfortunately, what one thinks matters in addition to how one lives: Lenin lived a bourgeois life as an exile in Paris and Zurich, but remained ever the radical at heart.

As we have seen, Wills wants to be understood as a conservative. Indeed, he writes, “One of the reasons I am a conservative is that I do not believe that ‘cannot’ should be removed from the dictionary. Recognition of limits is important to human life, and especially to human politics.” But he calls the importance of that recognition into question, immediately adding: “On the other hand, a defiance of human limits is an exhilarating prospect.” For Wills, the 1960s were a “fizzy time of youth and change.” Others, however, who really are conservative, would say that the country suffered a collective nervous breakdown. Wills not only found the 1960s exhilarating—it was also when he turned decisively to the left.

Pace his protestations, Wills is a liberal—albeit a liberal who is highly intelligent and at least something of a traditionalist when partisan politics aren’t at stake. I was reminded of this recently when he unleashed a witheringly sarcastic and completely justified attack, in the New York Review of Books, on two academics, Hubert Dreyfus and Sean Dorrance Kelly (the chairman of the Harvard philosophy department) for their new book, All Things Shining: Reading the Western Classics to Find Meaning in a Secular Age. To Wills’s dismay, the authors, far from defending the Western intellectual tradition, end up celebrating superficiality and attacking Western culture (particularly as embodied by Wills’s personal hero Augustine of Hippo) for its invention of “inwardness,” its search for deeper meanings in life. It was yet another bravura performance on his part.

Gary Wills is a living, breathing oxymoron in the Willsian sense of the word: a paradox who displays “a shrewd dumbness” in his writing. That is what makes Wills watching such an endlessly fascinating hobby. Read this book and you’re likely to take it up, too.

  1. Outside Looking In: Adventures of an Observer, by Garry Wills; Viking, 195 pages, $25.95.

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