Boris Yefimov, a Russian cartoonist despised by Hitler and beloved by Stalin who for 70 years and 70,000 drawings wielded his talent as a keen sword to advance the goals of his country, died in Moscow on Wednesday.
He was 109, old enough to have seen the last czar pass in a coach; become friends with Trotsky; have Stalin personally edit his cartoons; and vote for Vladimir V. Putin. In dispatches about his death, his age was first reported as 108, then corrected by his family.
When Mr. Yefimov was just 107, several Israeli newspapers reported that he was very likely the oldest living Jew, though he began to practice his religion only when he was 100.
Over almost the entire history of the Soviet Union, Mr. Yefimov's cartoons provided sharp commentary on subjects as varied as laziness on collective farms, bureaucratic inefficiency, the trials of Nazi leaders at Nuremberg, foreign policy trouble spots like Berlin and Yugoslavia, the Kennedy assassination and Mikhail S. Gorbachev's attempt to reform and salvage communism.
The most famous story about Stalin and Mr. Yefimov is about something that happened in 1947, when Mr. Yefimov drew a cartoon for Pravda that is sometimes described as an opening shot in the cold war. It showed Gen. Dwight D. Eisenhower arriving at the North Pole to find Eskimos and polar wildlife. Mr. Yefimov's caption had the general exclaiming that the greatest threat to American freedom was right there.
The pretext for the cartoon was a report that United States troops were penetrating the Arctic to counter a Russian threat. Stalin ordered the cartoon to illustrate how ludicrous he considered such an action. But it came at a time of mounting tension between the nations, and American media reported the cartoon as serious news.
The tension Mr. Yefimov felt was at least as intense. In 1940, for political reasons, Stalin ordered the execution of Mr. Yefimov's brother, Mikhail Koltsov, a leading Soviet journalist who had been the model for the character Karkov in Hemingway's novel "For Whom the Bell Tolls." His brother's death was very much in Boris Yefimov's mind when Stalin summoned him to hear his idea for a cartoon.
Mr. Yefimov told Stalin it was a great idea. The cartoonist did not know whether to rush to finish it quickly, or take more time to show how important he considered the project. He proceeded methodically, until Stalin called him at 3:30 the next afternoon. He wanted the cartoon by 6.
In an interview with Russian Life in 1999, Mr. Yefimov said, "A cold shiver went down my spine."
Mr. Yefimov was born as Boris Fridland in Kiev on Sept. 28, 1899, the second son of a Jewish shoemaker. Within three years, his family moved to Bialystok, which is now part of Poland. It was there that he began to draw, when he was 5, and saw Czar Nicholas II, when he was 11. He studied art and then law before going to Moscow to escape the chaos of the civil war in Ukraine.
In the 1920s, he and his brother changed their last name, Fridland, partly because it sounded Jewish at a time when anti-Semitism was on the rise. He got a job at Izvestia through his brother's connections.
Throughout his life, Mr. Yefimov was at the center of his country's cultural elite. He and the poet Vladimir Mayakovsky became friends, despite Mr. Mayakovsky's remark upon first seeing Mr. Yefimov's drawings.
"Rather poor, aren't they," Mr. Mayakovsky said, according to The Morning Star, a London newspaper. "In fact, very poor."
Trotsky, however, liked Mr. Yefimov's cartoons so much that he wrote the introduction to the first book collecting them, in 1924. Only reluctantly did the editor of Izvestia agree to print the words of Trotsky, who by then was on Stalin's bad side. The editor was executed for this decision.
But even after Mr. Yefimov's brother fell into disfavor with Stalin, he himself remained one of Stalin's favorites. Stalin criticized the buckteeth he gave Japanese characters as racist, but nothing happened to the man who drew them.
Mr. Yefimov worked for many prestigious publications, and some of his cartoons in effect became national icons, like the one showing frozen German soldiers carrying a coffin labeled "the myth of the invincible German Army." He received two Stalin prizes, among many honors.
Mr. Yefimov — who said his longevity might or might not have been affected by his taste for vodka, cognac and beer — married twice and outlived both his wives.