George Avakian and Cy Shain met in 1937, when Avakian was a freshman at Yale and Shain was a senior at DeWitt Clinton High School in the Bronx. They bonded over jazz, probably at the Onyx or Famous Door or one of the other clubs on West Fifty-second Street, and for the next seventy years they stayed in touch. On most matters–music, politics, baseball–they saw eye to eye. But on one thing they became great rivals, and it was serious business: the letters to the editor page of the New York Times.

It may now seem quaint, with even the greatest newspapers on the ropes, but for people of a certain age getting a letter published in the Times has always been a very, very big deal. Despite repeated attempts, Avakian, who became a legendary producer for Columbia and RCA Victor–Louis Armstrong, Benny Goodman, Johnny Mathis, Duke Ellington and Miles Davis were among the many icons he recorded–couldn’t buy his way into the paper. But Shain, who held a variety of government posts in judicial education and prison reform in California, managed to crack the code. And how.

Thirty-nine times over the past decade Shain, who lived in San Francisco, was in the paper on all manner of suitably weighty subjects: the Iraq War, campaign finance reform, the death penalty, nuclear proliferation. He had six letters printed each year in 2001, 2002 and 2003. People who have spent lifetimes trying to break into the Times might equate Shain’s record with Babe Ruth’s in 1920, the year he hit more home runs by himself than any other team in the American League. Meanwhile, in the Bronx, Avakian kept typing away–and striking out.

What explained their very different fates? It wasn’t politics: both were lifelong liberal Democrats who loathed George W. Bush and everything he stood for. In fact, it was only with Bush’s election in 2000 that their epistolary enthusiasms began; each was around 80 at the time. But there, alas, the similarities ended.

Avakian couldn’t contain his anger, and as anyone who reads the Times well knows, on the letters page no one ever gets too worked up about anything. Friends to whom he would sometimes send drafts forever urged him to tone things down. But try as he might–which, truth be told, wasn’t very hard–catharsis always won out over pragmatism. It started at the very outset of the Bush II era. “How many words have been written about the mess in Florida? 4 million, 400 million? 4 billion?” he wrote during the fiasco following the presidential election of 2000. “There are only four words which properly sum up the whole situation. They are: The fix is in.'” Of course, it got spiked. In another letter, from July 2007, he called Bush “the most flagrant liar in the history of the American Presidency.” Ditto. Three months earlier Avakian–like Shain, a World War II veteran–asked if Bush would view the Iraq War differently if his twin daughters had served there “and came home with one arm, one leg and one eye between them?” That, too, got nowhere. Worse, such letters seemed to poison the well for Avakian. Even when he wrote something more tempered or innocuous–bemoaning, for instance, that A-Rod’s home runs in the reconfigured old Yankee Stadium would have been mere fly balls back in DiMaggio’s day–it was rejected.

Shain’s letters, by contrast, were perfect Times material, which is to say, reasonable. When he raised the issue of the newly installed George W. Bush’s intellect and work habits, he did so gently. When he denounced the rush to war in Iraq, his tone was measured. His harshest adjectives were “sobering” or “bone-chilling” or “downright frightening.” And while Avakian was either blunt or discursive, Shain mastered the Times formula: invariably three sentences, or thoughts, first introducing, then elaborating upon, then concluding, an idea. Though he made his points, it was always with a jab rather than a roundhouse. Shain’s letters had the efficiency of haiku and the elegance of sonnets.

The Times has had more prolific correspondents than Shain; do a Nexis search sometime for Felicia Ackerman of Providence, Rhode Island, or Rachelle Marshall of Stanford, California, and see how often they come up. The paper offers no prizes for the fiftieth or hundredth published letter, nor would it: part of its mystique has always been that with multitudes clamoring to get into print, there’s no need for recidivists. But over the past ten years, Shain probably appeared as often as anyone. “You write a consistently thoughtful, articulate letter, with what we journalists call ‘sweep and scope,'” the paper’s letters editor, Thomas Feyer, once told him. (So good were they, Feyer went on, that when the paper devoted a clump of letters to a particular topic, it often put Shain’s on top.)

As he grew older, then lost his wife, getting into the Times became Shain’s way of keeping engaged with the world and in touch with friends, especially Avakian, since each appearance invariably led to an exchange of e-mails. Still, Shain took to waiting two months between attempts–in order, he once told Avakian, “to avoid wearing out my welcome.” The San Francisco Chronicle got his overage. A couple of times he even gave seminars around San Francisco on how to get letters published.

For all his frustration, Avakian was always magnanimous, even good-humored, about his friend’s successes. On occasion he’d send drafts to Shain, too, thinking, perhaps, that some of Shain’s magic might rub off on him. “As they used to say on Orchard St., ‘Nu?'” he wrote Shain in September 2006. Always, Shain was encouraging, counseling Avakian avuncularly–and futilely–to keep his efforts, as he once put it, “short and sweet and to the point.” For Avakian, all three were problems–especially the “sweet.”

Even the mighty Shain occasionally struck out. The Times wouldn’t let him liken Bush to a snake oil salesman, for example, or prophesy that Harding, Coolidge and Franklin Pierce would soon welcome him into the fraternity of worst presidents. But into early last year, his letters continued to appear: the only good thing about Bush’s State of the Union speech, he wrote in January 2008, was that it was his last. And but for one more effort that April, that letter turned out to be Shain’s swan song in the Times. Cancer and dementia took over.

Like most Times readers, Avakian didn’t notice that Shain’s efforts had ceased. But earlier this year, before heading to Los Angeles to collect a lifetime achievement Grammy award from the National Academy of Recording Arts and Sciences–he’d helped launch the organization fifty-two years before and is a past president–he began planning for a detour to see his old friend. His telephone calls and e-mails went unanswered, so when he reached San Francisco in early February, he went to Shain’s house. A neighbor told him a respirator had been rushed there a few weeks earlier and that Shain, who lived alone, hadn’t been seen since.

Shain had two daughters, but Avakian didn’t know their married names. Twice he went to Shain’s local post office to ask about him, only to get the runaround. He left town to collect his award without seeing Shain or learning what had happened to him. Twice he wrote San Francisco’s mayor, Gavin Newsom, asking for help tracking Shain down. Here too–as with all those letters to the Times–he got no reply.

Shain, it turns out, was still alive, in a hospice, when Avakian had come calling. But three days later, on February 10, he died. He was 88. For months before that, his daughters say, he’d withdrawn; still, their last picture of their father shows him reading, or at least holding–well, you can guess the publication, and maybe even the page. “I have many friends who, like myself, will miss Cy’s letters to the New York Times,” Avakian wrote the daughters after learning the news. Pleading with him to tone things down, his friends, he said, had always cited their father. “Unfortunately, the Times does not like my tone when I write about Republicans,” Avakian concluded, “and I refuse to change it.”

The Times has not acknowledged that one of its more reliable voices has been silenced. Even all those gentle pronouncements and well-mannered jabs on the letters page couldn’t win Cy Shain the ultimate Times encomium: an obituary. But undaunted, Avakian, who turned 90 on March 15, still sends in his letters. Some of them are about Obama, and since he actually likes the guy, maybe he, too, will now crack the code.