At the opening of his charming and absurdly readable memoir, “Outside Looking In: Adventures of an Observer,” Garry Wills remembers “a reviewer of one of my books in the 1960s [who] said that I did not really belong to the intellectual circles of that time. Though I seemed to be educated, I showed no influence from Freud or Marx, Nietzsche or Sartre, the stars of the fashionable intelligentsia.” Nearly half a century and a mind-boggling 42 books later (a couple of them compilations of his journalism for magazines), the same can be said: The greatest political commentator of our time still belongs to no trendy circles unless the circle could extend backward in time to one of his most profound influences (and the subject of his first book), G.K. Chesterton.

It was Chesterton who defined Wills’ political and economic ideals, such as Distributism, which was, in Wills’ words, “neither capitalist nor socialist, arguing for the preservation of private property but for its wider distribution.” The conservative William F. Buckley, who recruited Wills to write for National Review, told him that Distributism was “far from the free market capitalism … [that Buckley] considered the basis of modern conservatism” and that “Liberals … would soon be telling me that I could not belong to them either, since they were secularists — my religiosity disqualified me.”

Thus Wills maintains, correctly I think, that like Chesterton he remains an outsider, “incurably Catholic” in the words of one scholar, and, as Wills writes, “middle-class, never bohemian or avant-garde … ‘stodgy’ in my children’s eyes, puttering around my midwestern neighborhood unrecognized.”

Critics argue that a man who has amassed a friends list which includes Buckley, Studs Terkel (by self-definition an “old lefty”), the great quarterback Johnny Unitas, opera star Beverly Sills and cult filmmaker John Waters, to name just a few, is hardly justified in calling himself an outsider. But by Wills’ definition the term is valid. As he recently told an NPR interviewer, “I was always inside as an observer, never as a participant. I was never a member of a staff of a magazine, or newspaper, or political campaign, which I think helped me observe a little more passionately than I would have otherwise.”

book cover

Outside Looking In: Adventures of an Observer

By Garry Wills

Viking Adult, 208 pages

Buy the book

Wills might be called a passionate dispassionate observer. Virtually all of his long-term associations have come from his work as a writer, which has taken him to some unlikely places. One friend remarked that he never saw Wills “looking more out of place than when I sat on the floor of a stripper’s changing room, under a rack of scanty clothes, while ‘Tami True’ came off the stage and threw a robe over her pasties.” He has been thrown into jail (along with folk singer Judy Collins and photographer Richard Avedon) during anti-war protests (spending his time in stir reading Greek) and interviewed pestilential candidates on shaky, propeller-driven airplanes.

Of Richard Nixon (who put him on his enemies list because of a profile he had written), Wills argued, “He was not a right-wing extremist but an intellectually serious and prepared candidate, though one insecure and offensive.” Jimmy Carter, a failed one-term president in many people’s eyes, has had “the most successful ex-presidency of all time. No one else has made such an impact worldwide after leaving the nation’s highest office.” (I would look for Barack Obama to surpass that achievement.)

Wills makes a chilling and telling observation about Michael Dukakis, whom he overheard on a plane while covering his presidential campaign. Dukakis and a friend were discussing death. “You think of dying?” Dukakis asked. “Of course,” the man replied. “Don’t you?” “No, never.” “I was no longer surprised,” Wills concluded, “to hear such an answer from Dukakis. He is the supreme government wonk. If there is no government program against dying, why bother to think about it?”

Bill Buckley revealed to him how he beat a polygraph test upon entering the CIA: “I guess if you think you have a right to tell a lie, it will not register as one.” (Keeping his promise even after Buckley’s death, Wills does not tell us what the lie was.)

To see long excerpts from “Outside Looking In” at Google Books, click here.

Though Wills does not say it, his political sensibilities were surely shaped by Chesterton’s 1929 remark that the “business of the Progressives is to go on making mistakes. The business of the Conservatives is to prevent the mistakes from being corrected.” This explains why he has never pitched his tent in either camp. Nonetheless, Wills feels he has a right to define himself as a conservative. “One of the reasons I am conservative is that I do not believe that ‘cannot’ should be removed from the dictionary. A recognition of limits is importnat to human life, and especially to human politics. On the other hand, a defiance of human limits is an exhilarting prospect. …” One can only imagine Glenn Beck and Ann Coulter going cross-eyed at such a definition of conservatism.

The mainstream press has always been respectful of but a little puzzled by Wills, and now there’s less and less mainstream press out there. The left generally takes a patronizing tone toward his work and cherry-picks what it likes without bothering to consider the whole. The right has become so shrill and extreme that it almost ignores him altogether.

“Outside Looking In,” though, a book virtually devoid of politics, really seems to have some critics perplexed. In The Boston Globe, Bill Williams writes, “Wills lets us know that he has sailed with John Kenneth Galbraith and Walter Cronkite, as if it matters.” As if it matters is exactly the way Willis does not write about this; in fact, he mentions sailing with both men as an aside, in a parenthesis. (If you weren’t interested in such details, why would you read this book in the first place?)

In The New York Times, Dwight Garner criticized Wills’ “Steady drip of erudite but remote volumes. … Few of Mr. Wills’s recent books have warmed in your hands. They’ve been easier to admire than to embrace.” This is inexplicable. From 2005 through 2008 Wills wrote five books on Christianity. Perhaps Garner had no interest in the subject, but how can one characterize these books as “remote”? His book before “Outside Looking In” was “Bomb Power” (2010), about how the mere presence of nuclear weapons changed Western civilization; it is perhaps the only overheated book of Wills’ career.

Compared to most of his other books, “Outside Looking In” may seem slight, but after decades of dealing with such weighty subjects as the making of America, salvation and damnation, and the possibility of nuclear holocaust, Wills has earned the right to sit back, relax and talk about sailing, football, his wife Natalie, and anything else he damn well pleases.

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