In early 2009, as Malcolm Toon lay dying at age ninety-two in a hospital in Pinehurst, North Carolina, the New York Times had his obituary at the ready. That’s the way it is with someone like Toon, A37, F38, who leaves an indelible mark on the world—the Times plans ahead, to make sure that it can, at any moment, come out with an appreciation that does justice to the life lost. Toon was the former U.S. ambassador to Czechoslovakia, Yugoslavia, Israel, and, most famously, the Soviet Union, but after he died on February 12, 2009, his Times obit remained unpublished for more than eight years. Why? Because despite its preparations, the newspaper missed the news that he had actually died.

It wasn’t until this April that a Times editor named William McDonald began to suspect that something was amiss. Looking through the paper’s advance obits, McDonald saw that Toon was still in the files. “That would have made him close to a hundred years old,” McDonald said, “so out of curiosity I Googled ‘Malcolm Toon died,’ just to make sure that he was indeed alive.” What he found instead was that a local North Carolina paper had published an obituary in 2009. This was especially curious given McDonald’s discovery that the Times’ advance obit for Toon, originally written in 2006, had been substantially revised in 2010—a year after Toon had died. Somehow, in researching the ambassador’s life for the update, the writer “had seen nothing to indicate that Mr. Toon was dead at the time.”

When an obituary finally appeared in the Times on May 1, 2017, under the byline of staff writer Richard Goldstein, it not only memorialized Toon but marveled at how long his death had escaped the paper’s notice. After all, Goldstein wrote, Toon was “a leading State Department expert on the Soviet Union and Eastern Europe during the Cold War.” He was “characterized in the Times in December 1978 as becoming ‘one of the most influential postwar ambassadors in shaping the policy of the United States toward the Soviet Union.’”

Toon’s commanding knowledge of international affairs in general and the Soviet Union in particular sprang from a deep commitment to understanding the world in which he lived. In a 1989 interview with the American Diplomacy editor Henry E. Mattox, he explained that he had been drawn to Foreign Service work largely because of his childhood as a first-generation American. “My mother and father were graduates of Ellis Island,” he noted. In fact, the family moved from Scotland to the United States, and then back to Scotland, and then back to the States again. As a result of all that travel, Toon said, he “became interested in foreign cultures and languages. Then I started my schooling at Tufts University, and my interest in becoming a career diplomat intensified.”

In the years following his graduation, the country became embroiled in World War II. He joined the Navy, commanding a P.T. boat in the Pacific. After the war, he joined the State Department and opted for its Soviet specialist program. “At that time, unless you were a complete idiot, you had to recognize that the real problem of the post–World War period was going to be the Soviet Union,” he told Mattox. Toon served as a Foreign Service officer for several decades, became fluent in Russian, and, after a long string of high-profile positions, was appointed ambassador to the Soviet Union in 1976.

Toon set the blunt tone for his ambassadorship at his very first press briefing. Asked what his role in the Soviet Union would be, he is reported to have replied, “I think my job is to teach these guys how to act like a great power instead of some two-bit banana republic.” Toon would remain skeptical of the Soviets’ motivations throughout his nearly three years as ambassador to the country. For instance, in an address he delivered as the main speaker at Tufts’ commencement ceremonies in 1977, he said that even though he supported détente with the Soviet Union, he was concerned that some in this country may not be approaching it with open eyes. He believed that rather than anticipating “an era of good feeling,” we should “look to a period of reduced tensions.” He warned against “exaggerated and even false” hopes of affinity with the Soviets. Robin Knight, a former Moscow bureau chief for U.S. New and World Report, described his “core attitudes regarding the USSR and communism” as “acerbic, yet ultimately offset by innate diplomatic caution.”

Toon’s suspicion was not reserved for the Soviets, however. He was also skeptical of the trend later in his career toward awarding diplomatic posts as political favors. He once told the Los Angeles Times about an admiral he’d met who wanted to be an ambassador when he retired. “I replied that when I retired from the Foreign Service, I’d like to command an aircraft carrier,” Toon recalled. “The admiral said that was ridiculous because a naval command requires years of training and experience. I said, ‘That’s how it is with an embassy.’”

So how did the passing of such a distinguished, colorful, quotable diplomat elude the New York Times? The problem seems to have been a simple oversight. Publications typically learn that a person has died because someone close to the deceased sends a notification. In Toon’s case, his inner circle did get the word out to the news sources that appear to have mattered most to the man. There was the obituary that McDonald found in Toon’s hometown newspaper, and others in Fletcher News and the Foreign Service Journal. But the need to contact the Times apparently slipped everyone’s mind.

On the other hand, so did the need to contact any other national news organization, or even the State Department, and that, as McDonald pointed out, meant that, even eight years late, the Times had “something of a scoop.” McDonald, who has worked at the Times since 1988, said he could remember only one similar case: that of the Green-Beret-turned-antiwar-activist Donald W. Duncan, dead for seven years and memorialized only in a local paper in southern Indiana before the Times broke the story to the wider public.

In the big picture, Toon’s lack of a timely send-off from a national news organization hardly matters, of course. When he died, he was mourned by the important people: friends, family, neighbors, old classmates, old colleagues—those who’d had the privilege of knowing him personally. He was then laid to rest in Arlington National Cemetery, across the river from the State Department and beside his wife of fifty-three years, Betty.