People frequently ask what David Foster Wallace would have made of the Web. It’s a weird question, because Wallace, who died four years ago, actually lived well into the Internet era, even unto the age of Facebook and Twitter. But reading Wallace or reading about Wallace it doesn’t feel that way. When he wrote about how the media permeates all of our actions and thoughts he was referring to television. The plot of “Infinite Jest” hinges on the whereabouts of a short movie so entertaining that it kills whoever watches it. But even in 1996, a videocartridge would have seemed a little dated.

Not everyone took this plot device at face value, though. When Infinite Jest came out, the more perceptive critics tagged it, with its schizophrenic narrative movement and overstuffed cabinet of characters, as actually about the Web. The book, instructed Sven Birkerts in a review in the Atlantic, “should be seen… as a response to an altered cultural sensibility.” To which Wallace demurred, “This is sort of what it’s like to be alive… . You don’t have to be on the Internet for life to feel this way.” He added that he had never been online.

Looking at the wonderful inside cover of one of Wallace’s notebooks from the archives at the Ransom Center in Texas, dating from around 1999 (pictured above, click on the image to expand), you can see that although Wallace was likely exaggerating his Luddite stance, he was not exaggerating by much. What more analogue technology is there than scotch tape and scissors? Wallace used his improvised bulletin board for dictionary definitions, starts on plot ideas, a quote from Beckett on how hard it is to write, a little happy-face squiggle, plus his mailing address with the offer of a reward in case the notebook goes missing.

All the same, if Wallace disliked the new technology personally, he could hardly help being curious about its effect on what he called “old eternal verities.” And so, likely with the help of a researcher, shortly after changing his number yet again to keep ahead of his fans (note the crossed-out phone number on the notebook flap) he began thinking about this vast new source of information and images. The result was “Wickedness,” an unfinished story from around 2000, now part of the newly opened Pale King boxes in the David Foster Wallace papers at the Ransom Center.

Until I saw “Wickedness,” I did not know that Wallace had ever left a stand-alone story unfinished. He tended to recycle what he wrote, and so stories became sections of novels and sections of novels were calved off into stories. But “Wickedness” (also “Wickeder”) appears to connect to no other Wallace project. Maybe it was the start of a new novel, maybe it was meant to be a short story, maybe it was an exercise in voice or a response to the noir novels he enjoyed. In its pages, he returns to the great theme of “Infinite Jest”: the lethal power of media. Only this time, he posits that the locus of our self-annihilation has moved online.

The plot of “Wickedness” centers on a tabloid reporter named Skyles who, dying of cancer of the mouth, is trying to shoot pictures of Ronald Reagan beset by Alzheimer’s for the Web site Wicked.com. Reagan’s privacy at the San Placido Institute—“the Betty Ford of nursing homes,” Wallace calls it—is a matter of not just his own security but also the nation’s: we need to remember him as he was, powerful and in command. “The nation’s morale could be affected, the integrity of the social order,” Wallace writes. “At a certain point their lives are no longer their own.” Skyles’s motive seems to be revenge: a pair of old tabloid buddies have visited him on his boat The Rodent, and revived in him the outlaw pleasures of transgressive photography. (Though Wallace voted for him twice, his choice of Reagan as Skyles’s target seems more plot than emotion driven, but he does get in a few digs in at various public figures: Nancy Reagan’s secret service name, for instance, is Mantis.)

The issue of the media’s increasingly ferocious invasions of privacy was one that Wallace felt acutely after the publication of “Infinite Jest.” In “Wickedness,” the old tabloids—The Star, The News of the World—repulsive as they were, are depicted as playing by rules, but the new ones do not. “Despite all the hoopla about populism and information,” Wallace writes of the Web, “what it really was was the bathroom wall of the U.S. psyche.” He invented for the story the sites Latrine.com, 10footpoll.com, and filth.com, which will stop at nothing to publish humiliating photos of celebrities: “Of this Senator’s penile implant (his pacemaker interdicted Viagra, the RN they’d bought off confided). Of the aging TV actress’s horror and seclusions since the plastic surgery she had to repair the botched face-lift itself was botched and left her with eyes 6” high…. Of William Shatner toupeless.”

What has changed? When Wallace wrote a long piece on the adult-entertainment awards, in 1998, he asked Premiere to order the videos in competition and ship them to him in Bloomington, Illinois. But in the era of the Internet, such shame is removed. Public vices have become private obsessions. The porn theatre has disappeared and the porn video flourishes. “ ‘Title of movie not shown on bill’ tripled hotels’ in-room porn revenues,” Wallace writes at one point. So, too, the Web’s appetite for destructive journalism: we are no longer ashamed to read tabloid news, because it just comes to us on the computer. We don’t choose it; it infiltrates our air. It’s not that these ideas were so new, even in 2000, but in a Wallace story, the statement is conveyed with such intensity that it feels discovered anew. One can see in the margins of the story example after example added of privacy shredded. You sense that Wallace is genuinely mad about it—and intrigued, taking on the persona of the guilty “ogler” he describes in his own essays. “Wickedness” is prescient—one thinks of the blandly shameless mix of crime and sex stories on the AOL home page—but, most of all, it is powerfully wrought.

Wallace wrote the story in the characteristic tiny, forward-charging handwriting with which he attempted new fiction—what he called “freewriting.” (I owe thanks to James Lamon, a recent University of Texas graduate and Wallace scholar, for his deciphering of these and other scribbles). The story stops suddenly with Skyles, masquerading as a maintenance man, with a camera hidden in his apron at the nursing home, trying to catch the Gipper drooling. It is not clear whether he will shoot the pictures or renege, and what Wallace thought of any of the four thousand or so words he had come up with at this point is also a mystery. “I’m trying,” he writes touchingly along the left margin of the first lined notebook page. And elsewhere, “Blankness is OK.”

Blankness in the end won out. But not before Wallace deftly drew a protagonist who pushes the James Ellroy hard-boiled model over into the grotesque. Wallace, as ever, is interested in how much honesty we are capable of, the way we use our eyes as social censors—half of Skyles’s face has been destroyed by a cancer and replaced with “a hardened latex appliance fit over his right profile—they pretended it was to keep the wound sterile.” Skyles in turn admires a secret-service agent who has the courage to look at him.

In one final twist, there is a sense, “Infinite Jest”-like, that foreign governments are aware of the power of this new technology mated to our ancient self-destructive appetites, the way we Americans always latch onto what is worse, in order to hide all that is empty within ourselves. To that end, there is an interesting note in the margins on the last page: Internet Site Owned by Russians. But, as with the rest of the story, Wallace never followed up on the idea.

D.T. Max is a New Yorker staff writer. His book “Every Love Story is a Ghost Story: A Life of David Foster Wallace” was recently published.

Read more of D.T. Max's posts for Page-Turner.

Photograph courtesy of David Foster Wallace Literary Trust/Harry Ransom Center.