Samuel Untermyer, a hard-nosed lawyer, an eagle-eyed investor, a big-hearted civic leader, and a green-thumbed horticulturalist, was torn when America fought Germany in World War I—only to be among the first Americans to turn on Hitler’s Germany, long before America entered World War II.

In truth, Untermyer’s nostalgia for his ancestral homeland in 1917 was far more characteristic than his fiery advocacy 16 years later. Born to German Jewish immigrants turned Confederate supporters in 1858, Untermyer described himself “as one of German parentage, whose ancestors were for centuries imbedded in the soil of that land,” and someone with the “strongest feeling of sympathy toward the German people.”

Indeed, Untermyer grew up in the clubby confines of the German immigrant elite. His law firm was a partnership of German-American relatives. He even married a non-Jewish German woman Minnie Carl. But within weeks of Adolf Hitler’s coming to power in January, 1933, when most German Jews were deciding to stay in Nazi Germany—and most Americans were trying to appease it—Untermyer understood what was happening...

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