Thompson was sixty-seven when he ended his life: young by actuarial standards, but older than he ever thought he would be. He’d had a hip replaced and he was in constant pain from nerves impinging on his spine. A month before his death, during a trip to New Orleans, Thompson planned to attend a party given by his politico friend James Carville, but he was in a wheelchair and wouldn’t let people carry him up to the dining room. And he knew what everyone else knew: that he’d done his best work twenty years before. Brinkley, like Thompson’s first wife, Sandy, partly blames cocaine—which Thompson called “a worthless drug” even as he snorted it—for the long, slow slide. And self-inflicted celebrity got in his way. After the 1972 campaign, he was too famous to do much reporting: wherever he went, he became the story, no longer just for himself, but for other reporters. Rolling Stone miscast him as a war correspondent during the fall of Saigon in 1975: he missed the evacuation while trying to buy eavesdropping equipment in another part of the city. The previous year, he’d gone to Zaire for the Ali-Foreman fight, and missed that, too. He was in the hotel pool, floating around with a pound and a half of pot he’d thrown in—and he didn’t even file that story. For the rest of his career, he was essentially an armchair commentator, retooling his Nixon-era outrage to fit Ronald Reagan, Bush forty-one, Bush forty-three.

It’s painful to read the accounts, both in McKeen’s biography and in Conversations, of the aging Thompson commanding his Woody Creek visitors to read his work aloud, and insisting that they slow down in order to bring out the rhythmic nuances. You can’t help but be reminded of King Lear coercing his daughters to demonstrate their love through flattery: it suggests an unassuagable insecurity. Sandy, who asked him for a divorce in 1978 when she could stand no more of his drugging and womanizing, considers Thompson a failure on his own terms. “He was a tortured, tragic figure,” she told McKeen. “I do not think he was a great writer . . . . He had the genius, the talent, and, early on, the will and the means. He was horrified by whom [sic] he had become and ashamed . . . . He knew he had failed. He knew his writing was absolutely not great. This was part of the torture. And yet, he could never climb back. The image, the power, the drugs, the alcohol, the money . . . all of it . . . he never became that great American writer he had wanted to be. Nowhere close. And he knew it.”

But how much great work can any writer do in a lifetime? Fitzgerald and Hemingway, Faulkner and Twain, all produced more tailings than gold. Thompson left us one canonical classic (Fear and Loathing in Las Vegas), the funniest and darkest book ever written about the American political process (Fear and Loathing: On the Campaign Trail ’72), and volumes of letters rivaled in American literature only by those of Ezra Pound for their voice and vigor. It should have been enough to satisfy anybody but Thompson himself.

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David Gates is the author of the novels Jernigan and Preston Falls and a collection of stories, The Wonders of the Invisible World. He is a former senior editor at Newsweek, where he wrote about books and music, and his nonfiction has appeared in The New Yorker, GQ, The Oxford American, The Journal of Country Music, and many other publications.