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 Putin.

When Yefimov was 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.

The death of Yefimov, whose name is sometimes transliterated from the Cyrillic as Efimov, was widely reported by Russian news media. Some reporters could not resist leading with his oddly warm but necessarily precarious relationship with Stalin, that famous lover of cartoons.

Others first mentioned Hitler, whom Yefimov depicted as a sinister mix of the crazy and creepy. Hitler vowed to shoot the cartoonist as soon as he captured Moscow.

Over almost the entire history of the Soviet Union, 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 such as Berlin and Yugoslavia, the Kennedy assassination and Mikhail S. Gorbachev's attempt to reform and salvage communism.

Cold War cartoon

The most famous story about Stalin and Yefimov is about something that happened in 1947, when Yefimov drew a cartoon for the newspaper 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. 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 U.S. 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 Yefimov felt was at least as intense. In 1940, for political reasons, Stalin ordered the execution of 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.

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, Yefimov said, "A cold shiver went down my spine."

Yefimov finished on time. For many years, the original cartoon, with Stalin's personal editing marks in red pencil, hung on his wall.

'Rather poor' drawings

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. 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 the newspaper Izvestia through his brother's connections.

Throughout his life, Yefimov was at the center of his country's cultural elite. He and the poet Vladimir Mayakovsky became friends, despite Mayakovsky's remark upon first seeing Yefimov's drawings. "Rather poor, aren't they?" Mayakovsky said, according to The Morning Star, a London newspaper. "In fact, very poor."

Trotsky, however, liked 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 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.

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.

Yefimov said he hated Stalin for killing his brother but was proud of the Soviet Union's successes and glad he propagandized about them. He told Russian Life, "When you are a political cartoonist, you have to keep pace with politics."

Yefimov married twice and outlived both his wives.

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