In all the rarefied rooms through which he moved with leonine grace in the prime of his life, Ben Bradlee benefited from a singular gift: everyone he encountered wanted to be like him or with him. He wore the honor as lightly as one of his trademark bold-striped shirts.

Since Bradlee’s prime constituted (more or less) the last half of the 20th century—and a few good years of the 21st—his admirers amounted to an honor roll of his era. Not for nothing did he call his memoir A Good Life, a title that he suggested, with typical insouciance, was better than Personal History, the Pulitzer-winning memoir of his Washington Post patron, Katharine Graham.

Bradlee’s self-confidence was the stuff of legend, and, as the saying goes, when the legend becomes fact, print the legend. When he walked through the newsroom of the Post that he single-handedly had made (in Post editor Meg Greenfield’s words) “dangerous to people in government,” he clanked between the waist and knees (as he would have himself confessed). Lesser men, and lesser journalists, would have given their “left one” (as he also would have put it), to have a tenth of his talent, fame, or wealth.

His pedigree was Brahmin and his blood was blue. His maternal great-uncle, Frank Crowninshield, was the founding editor of Vanity Fair. He spoke grammatically perfect French with an unyielding Boston accent. He survived four years of naval service on destroyers in the Pacific during World War II and made a splash as Newsweek’s man in Paris in the golden days of the postwar 1950s. But his greatest break came through a willful bit of luck, when he found himself the Georgetown neighbor of his fellow Harvard graduate, Senator John F. Kennedy, when they and the world were both still young.

They shared parties and children and drinks and danger. (And, if Kennedy had had his way at the last birthday party of his life, they might have shared Bradlee’s second wife, Tony, too. Tony confessed decades later to V.F.’s Sally Bedell Smith, for her book Grace and Power, that J.F.K had chased her around the presidential yacht during a long and bibulous night—which Bradlee claimed was news to him.) When Kennedy became president, Bradlee enjoyed access to the White House that was then extraordinary and that would be inconceivable today. Did he know of Kennedy’s sexual recklessness? To his last sentient day he insisted he did not, explaining that they had mostly been together in the company of their wives, where such exploits would have been unlikely conversational grist. A fair point, but an asterisk on history’s ledger all the same.

Bradlee’s Kennedy scoops ended with the assassination—and his friendship with Kennedy’s widow, Jacqueline, dwindled, too. Their bond was severed entirely after Bradlee published Conversations with Kennedy, in 1975, a volume that proved he’d been keeping copious contemporary notes of conversations with the president a decade earlier that Jacqueline considered confidential.

But his Kennedy White House coverage—compromised or comprehensive (take your pick)—was as nothing compared to what would follow.

So many of Bradlee’s greatest achievements are enrobed in a glow that is too good to check. His recommendation that The Washington Post’s publisher Philip Graham buy Newsweek, leading to a hefty finder’s fee in Post stock, which turned into a fortune when the company went public; his crusading editorship of the Post through the Pentagon Papers and Watergate (not every editor can claim the honor of being portrayed by Jason Robards); his—and his third wife, Sally Quinn’s—purchase of Robert Todd Lincoln’s Georgetown home for a then-record-setting price.

Regrets? He had a few, among them the failure of his first marriage to Jean Saltonstall, a fellow Bostonian, and the inadvertent hurt he had caused her upon his return from the Navy when he’d seen so much and she had not. (He confessed as much to Charlie Rose on TV).

Doubts? Only a few recorded, among them—in a scribbled, torn note never sent to Quinn, the onetime star Post reporter who captured his heart, before their marriage—whether Quinn loved him only for all the wrong reasons. That missive became public via Bradlee’s Eve Harrington amanuensis, Jeff Himmelman, a young researcher for Bob Woodward to whom Bradlee had given carte blanche to mine his papers, and who found in them no little lead among the gold. Himmelman, in his controversial 2012 memoir-biography, Yours in Truth—which turned trust into tell-all, but was heavily documented—also chronicled how the children from Bradlee’s first two marriages sometimes envied (and often resented) the attention—which is to say, love—that he lavished on the frail but plucky son from his third.

Bradlee’s management of the Post was brilliant—capricious, instinctive, sometimes wrong but never dull. He played favorites. He pitted rivals against each other, to make them better. He kept people on edge, as he himself actually was, whatever surface cool he pretended to affect.

In the late 60s, when he hired the superb Eugene Patterson as his managing editor, the partnership came a cropper. “I thought he was kind of a clever dilettante,” Patterson told David Halberstam for The Powers That Be, Halberstam’s definitive history of The Washington Post, CBS, Time magazine, and the Los Angeles Times. “But he is ruthless and he is tough and he is smart and able and very much in charge of the paper. I made the mistake of thinking that he needed me, and he did not.”

I can’t claim to have known him intimately, but I treasured our occasional intimate encounters over 20 years. His gleeful, resilient vulgarity—a hard-earned sailor’s privilege—leant hope to the most embarrassing moments, as it did when I explained some predicament to him at a friend’s wedding, and he replied, “Well, that was a shit sandwich, for sure.” When I left The New York Times for V.F. after 23 years, I met him at a Washington Christmas party and confessed that I didn’t think daily journalism was much fun anymore.

“It hasn’t been fun for a long time, pal,” he said.

But nothing looms larger in my memory of Ben than the night of a post-9/11 book party for our mutual friend, Haynes Johnson, whom Ben had hired and turned into the Post’s past master of political pulse-taking for a generation. Haynes had just had the bad luck in that fearful moment to publish a very good but suddenly irrelevant book called The Best of Times: America in the Clinton Years. I arrived late—delayed by some chaotic assignment in The Times’s Washington Bureau (Was it anthrax? The sniper? The hell if I can remember, but I was beat)—to a book party given by Haynes’s great friend, Marcia Hale, whose elegant house in northwest Washington sits atop a long, steep, stone staircase.

In the foyer, I found Ben in deep conversation with my wife, Dee Dee Myers, as the party was winding down, and the house was emptying. In a dyslexic faux pas, I reached over to pump her hand, and leaned in to kiss his lips. He kissed me right back and then reeled. “Wow!” Sally, approaching from the corner, asked, “What about me?”

I blushed, and broke out in a fabulous flop sweat. The next day, I sent him a short note, trying to explain how only post-traumatic stress disorder could have led me to give a shake to my wife, and a kiss to my career idol. I begged his pardon.

By return mail came a bright-blue-and-white personal notecard, with this piquant and perfect scrawl: “Dear Todd: Who would I ever tell?”