Wodehouse and Milne were the same age and from the same class. They socialized and played cricket together, and Milne put up some money for a stage adaptation of one of Wodehouse’s novels. Their careers ran in parallel for a while, both writers striving in various forms and media, particularly theater and fiction. Both men became very popular writers on both sides of the Atlantic, Wodehouse for his farcical novels about British twits and Milne for his four volumes of children’s verses and stories.
After Wodehouse was interned by the Germans near the start of World War 2 and recorded a few radio broadcasts for the Reich in 1941, many British authors wrote public letters lambasting him. Milne was among the sharpest critics. He reminded newspaper readers that Wodehouse had spent the previous World War far away in America and had moved around in the 1930s to find tax havens.
Many analyses of the rift say Milne was jealous of Wodehouse’s success. Wodehouse himself advanced this idea in his 1975 interview with The Paris Review, and it may have been true. The Milnes do seem to have been capable of nursing great resentment over time.
However, both authors were tremendously successful. The difference was that Milne hated how the public and critics had pigeonholed him while Wodehouse embraced those limits. Milne kept trying to write adult novels, plays, mysteries—anything but children’s books. Wodehouse had stopped writing quasi-serious novels like The Coming of Bill and musical comedies and dove into the capers his readers wanted. He also eschewed politics while Milne kept writing about that concern.
Another factor not usually noted is that Milne had helped his son Christopher join the British military. I don’t think it was coincidence that as another example of Wodehouse’s irresponsibility Milne quoted his quip that he wouldn’t care about a son until he was in the First Eleven. Milne knew that Wodehouse had no sons, and thus no sons in the war. (Yet another factor: Milne had been pacifist until shortly before the war, so he wrote with the zeal and gnawing conscience of a convert.)
Ironically, Wodehouse’s stepdaughter Leonora, whom he was very close to and who telegraphed him to stop broadcasting, died in 1943. Thus, by the time Wodehouse was free to digest the controversy, he had actually lost a child during the war. Christopher Milne survived to carry on his own resentments.
Twice in the 1950s Wodehouse, now permanently settled in America, used his fiction to attack Milne. In 1975 he claimed to have gotten over the feud, at least enough to appreciate Milne as a writer, but by then Milne was dead.