Lionel Trilling and Donald Trump were both lifelong New Yorkers, but it’s safe to surmise they never met. Trilling (1905-75) was an English professor at Columbia and America’s last great literary critic. He wrote penetratingly about a Trumplike figure—Rudyard Kipling. Kipling (1865-1936) was of course the English novelist, short-story writer and poet. Much of his work, such as “Jungle Book” and “Kim,” was beloved in his time and is still read in ours. But Kipling had a political problem. Like Mr. Trump, he was viewed by many of his critics as a fascist.

Trilling...