Cathy Young is contributing editor of Reason magazine and author of Growing Up in Moscow: Memories of a Soviet Girlhood.

The death of Soviet political cartoonist Boris Yefimov on October 1, largely unnoticed in the West, was not quite the end of an era--Yefimov's era ended long ago--but the end of a life that, Zelig-like, was involved in every transition of the last century of Russian history. More than a century, in fact: Yefimov (born Boris Yefimovich Friedland, in Kiev in 1899) was 109 years old when he died. As a boy, he watched Russia's last Czar Nicholas II go by in a coach. Four days before his death, he spoke to Dmitry Medvedev, who telephoned to wish him a happy birthday. He was present for the birth of the Soviet Union--and outlived it. One of the Soviet regime's most faithful servants, he was also in some ways its victim, losing a brother to Stalin's reign of terror. Such paradoxical accommodations were the essence of Yefimov's career, and his survival. In an interview last February, Yefimov said that the secret of his longevity was "a philosophical outlook on the vicissitudes of life. I didn't get too agitated over anything, not even when my brother was shot and I bore the mark of 'a relative of an enemy of the people' for 16 years." 

A talented graphic artist from his childhood days, he threw in his lot with the revolutionary cause as a young man, becoming a cartoonist for communist newspapers. He was befriended by Leon Trotsky, who wrote a foreword to Yefimov's first collection of cartoons in 1924. (The publisher of that collection was later shot; Yefimov lived to draw Trotsky as an evil-looking dwarf in a helmet with a swastika.) In 1938, Yefimov's older brother, journalist Mikhail Koltsov (the prototype of "Karkov" in Hemingway's For Whom the Bell Tolls), was arrested on charges of Trotskyism and later executed. In Stalin's Russia, a brother of an "enemy of the people" was always one knock on the door away from the gulag. For a while, Yefimov lay low, toiling as a book illustrator. In 1941, he returned to political cartoons and eventually became Stalin's favorite--a court artist to the Red Czar whom, he later said, he hated, dreaded, and revered at the same time. The conflicts of his position were many: Himself a Jew, he lent his acerbic pen to Stalin's anti-Semitic witch-hunt against "the murderers in white coats," the Jewish doctors accused of plotting to murder Soviet leaders. 

For more than 35 years after the death of "the Boss," Yefimov continued to work for the Soviet propaganda campaign du jour. Nothing if not adaptable, however, he adjusted well to the fall of communism, even drawing humorous advertising sketches for the Moscow office of Radio Liberty, which he had once lampooned as a den of anti-Soviet iniquity. At 100, he became a practicing Jew for the first time in his life. Among his last works was a 2007 poster that depicted a pipe-smoking Stalin trampling a rainbow with his boots. 

It would be easy to see this man as a cynical monster--and perhaps he was. Yet, curiously, Russian liberals who commented on his death, such as Ilya Milshtein, a columnist for the independent website Grani.ru, were reluctant to throw stones. It was as if the sheer length of Yefimov's life, his fantastic journey as a witness to several ages, inured him to attacks. Milshtein's obituary of Yefimov ends on a pessimistic note: "One is tempted to ask, is there a point in living a long life in Russia? ... If you're born under Nicholas II and die under Medvedev, it seems like a rather hopeless life." That's one way of looking at it; but one could also see in such a life a stark reminder of the fragility of oppressive regimes. Because no matter what sacrifices of integrity it may have required along the way, Yefimov survived a century of wars, revolutions, and murderous dictatorships to draw about them all.

(For more examples of his work, click here, here, and here.)