The compound consisted of seven buildings—“seven moons orbiting a dead planet,” as it is described in “Infinite Jest”—all leased to various substance-abuse and mental-health assistance groups. Wallace met Deb Larson, the director, at his new temporary home. Tall and blonde, she walked with a limp: drunk, she had fallen down in her kitchen, hitting her head, causing a partial paralysis. Even then she hadn’t stopped drinking. Wallace respected her. She was pretty and smart and gave him a link to an old life that was still his present—you could almost see Harvard from the top floor of the building. Recovery facilities tried to control the stress levels of their participants, and one activity they generally prohibited was school. Wallace had no choice but to call the philosophy department at Harvard and ask for a leave of absence. He was too humiliated to go back to get the vegetable juicer, a gift from his mother, that he had left behind in the graduate office.

Wallace was expected to find low-level work. The writer, whose only real skill was teaching and writing, cast around and was able—probably thanks to the presence on his resume of the head of Amherst College security as a reference—to get hired as a guard at Lotus Development, a large software company. Granada House rules stipulated a forty-hour workweek, so Wallace got up at 4:30 in the morning to take the Green Line subway and worked until 2 P.M., walking to a vast disk-packaging plant in Lechmere, clocking in his whereabouts every ten minutes and twirling his baton (or so he later said). He would tear pages out of his notebook and send letters to his friends, maintaining contact with the small group of editors and writers who were vital to him. The Lotus experience, he recalled in a later interview, reminded him of “every bad ’60s novel about meaningless authority,” but at the time he bore it well. “Give me a little time to get used to no recreational materials and wearing a polyester uniform and living with 4 tatooed ex-cons and I’ll be right as rain,” he wrote the editor and literary critic Steven Moore with ironic brio shortly after starting. Even inside Granada House, he managed to attend to the business of being a writer—following up on submissions to magazines and reading pages of stories he had coming out. He could see the strange side of his situation. When the galleys of his story “Order and Flux in Northampton” arrived from Conjunctions with a page missing, he told his editor Brad Morrow he could send it at his convenience. “I’m not going anywhere for Xmas,” he wrote.

But in his heart he was stunned with what had happened to him. “I am,” he wrote his former professor at Amherst Dale Peterson, “OK, though very humiliated and confused.” He was sharing a barracks-like room in Granada House with four men, one of whom, he wrote Rich C., who had been his twelve-step program sponsor the year before, had had a stroke while on cocaine and had a withered right side. “Mr. Howard,” he told his Norton editor, Gerry Howard, “everyone here has a tattoo or a criminal record or both!” To Peterson he reported, “Most of the guys in the house are inmates on release, and while they’re basically decent folk it’s just not a crowd I’m much at home with—Heavy metal music, black t-shirts & Harleys, vivid tattoos, discussion of hard-vs.-soft-time, parole boards, gunshot wounds and Walpole—” Massachusetts’s toughest prison. Wallace continued at his security job for more than two months, and then, unable to bear getting up so early, he quit. He went to work as a front desk attendant at the Mount Auburn Club, a health club in Watertown. His job was to check members in—he called himself a glorified towel boy—but one day Michael Ryan, a poet who had received a Whiting Award alongside him two years before, came to exercise. Wallace dove below the reception desk and quit that day.

Wallace’s friends were accustomed to his exaggerations and inventions over the years—they came with his clownish, hyperbolic persona—but when they visited him at the halfway house, they found that what he said was true: he had stepped through the looking glass. His friend Debra Spark, a fiction writer, remembers sitting in on a group therapy session with Wallace one day and being amazed to hear someone recount killing someone while drunk. All the same, Wallace found his place; order, no matter how foreign the context, was always easier for him than the unstructured world. He met with a counselor, as required, and nearly every evening he drove to different parts of the city with other Granada House members for substance-abuse meetings. His sponsor was named Jimmy, “a motorhead from the South Shore,” as he called him to the novelist David Markson, with whom he had begun a correspondence. Wallace read the Big Book and enjoyed making fun of its cheesy 1930s adman vocabulary to his friends: “tosspot,” “Dave Sheen heels,” “boiled as an owl.” “He laughed at them, but he also knew he needed them or he would die,” Mark Costello, who visited him at Granada House, remembers.

If Wallace found himself in unfamiliar territory, the residents didn’t know what to make of him either. One remembers wondering, “This guy can probably go to Betty Ford. Why’s he here with us welfare babies?” No one really cared for his cleverness. He was to them a type they’d seen before, someone who, like the character Geoffrey Day in “Infinite Jest,” tries to “erect Denial-type fortifications with some kind of intellectualish showing-off.” Wallace was back in high school, trying to figure out his place in the pack. “It’s a rough crowd,” he wrote Rich C., “and sometimes I’m scared or feel superior or both.” Yet a piece of him was beginning to adjust to the new situation. He remembered his last failed attempt to get sober and how he was no longer writing and asked himself what he had to lose. He came to understand that the key this time was modesty. “My best thinking got me here” was a recovery adage that hit home, or, as he translated it in “Infinite Jest,” “logical validity is not a guarantee of truth.” He knew it was imperative to abandon the sense of himself as the smartest person in the room, a person too smart to be like one of the people in the room, because he was one of the people in the room. “I try hard to listen and do what [they say],” he wrote Rich C., “I’m trying to do it easy … this time,” not “get an A+…. I just don’t have enough gas right now to do anything fast or well. I’m trying to accept this.”

Not that things came easily. The simple aphorisms of the program seemed ridiculous to him. And if he objected to them, someone inevitably told him to do what was in front of him to do, driving him even crazier. He was astonished to find people talking about “a higher power” without any evidence beyond their wish that there were one. They got down on their knees and said the Thankfulness prayer. Wallace tried once at Granada House, he told Costello, but it felt hypocritical. (All the same, Wallace liked to quote one of the veteran recovery members, the group known in “Infinite Jest” as “the crocodiles,” who told him, “It’s not about whether or not you believe, asshole, it’s about getting down and asking.”)