He Was a Lifelong Con Man. His Biggest Mark: Adolf Hitler.

On February 18, 1937, Freeman Bernstein eased his pudgy 63-year-old body out of the back seat of a rented limousine at the Hollywood home of actress Mae West. Thirty years earlier, Bernstein had been West’s agent, booking her in vaudeville shows. Now he was hawking jewels he’d smuggled from China. A tough customer, West bought some rubies and sapphires but rejected the cheap zircon that Bernstein tried to pass off as a diamond. Then she autographed a picture for her guest, writing “To Freeman Bernstein, who was my first agent at the age of 10.”

Bernstein took West’s check and the picture and instructed his chauffeur to drive him to the Brown Derby restaurant. On the way officers of the Los Angeles Police Department stopped the limo and arrested Bernstein: He was wanted in New York for swindling the German government out of nearly $150,000 by selling the Nazis a load of what was supposed to be valuable nickel but which turned out to be scrap metal.

“Adolf Hitler was on bended knee begging me to help him get some nickel,” Bernstein told reporters the next morning. “Hitler got just exactly what he paid for in that deal—scrap steel and nickel—and I’ll prove it.”

The tale of an American accused of swindling Hitler made news nationwide and inspired a cringe-worthy Wisconsin State Journal headline: “Jew Denies Gyping Hitler in Junk Deal.”

Actually, Bernstein did bilk Hitler—or at least the Führer’s government—but that wasn’t surprising. He’d been flimflamming suckers on several continents for decades. Bernstein was a carny, a card sharp, a con man, a shady showbiz promoter, and a racehorse owner so crooked he was banned from tracks in Canada, Mexico, and Austria. But he was charming and persuasive and he convinced countless dupes to invest in his dubious schemes.

“Even when fleecing the gullible, he did it with such infectious high spirits that he believed the marks didn’t really mind,” Walter Shapiro wrote in Hustling Hitler, his wry 2016 biography of the grifter.

Freeman Bernstein was born in 1873 in Troy, New York, son of Polish immigrants. He quit school after fifth grade and at 13 experienced the first of many arrests, for stealing $10 from the pocket of a man who’d doffed his clothes to swim in the Hudson River. Bernstein drifted into the carnival business, receiving a valuable education in the art of the grift. By the early 1900s, he was a low-rent impresario, booking vaudeville acts in the boonies. The troupes he hyped as “The Greatest Aggregation of Vaudeville Talent Ever Brought Together” consisted mainly of has-beens, wannabes, and goofy novelty acts—a one-legged acrobat, a dwarf comedy team, and “the white man who sings coon songs.” 

When a performance failed to draw a crowd, Bernstein would grab the box office receipts and flee on the next train, leaving his performers stiffed and stranded. In 1912, he took a 45-member opera cast to Puerto Rico; when the show failed to attract audiences, he skedaddled. “He’s left stranded troupes all over the world,” the editor of Variety, the showbiz newspaper, lamented.

In 1915, inspired by the huge success of the movie Birth of a Nation, Bernstein created a film company, found impressionable investors, and produced two movies, both starring his wife, singer May Ward. When the first, a Revolutionary War drama entitled A Continental Girl, tanked, Bernstein made his second movie steamier. In Virtue, Ward played an innocent farm girl lured into sexual slavery. Bernstein billed the film “the Most Striking, Realistic and Sensational Film Ever Presented.” Alerted, censors in Philadelphia and New York banned Virtue. Bernstein recouped his losses when a mysterious fire incinerated his movie studio, which he’d presciently insured. He showed a Variety reporter the policy, saying, “See, I told you there was money in pictures.”

Ah, so many Freeman Bernstein scams, so little space:

During World War I, he set up carnivals outside army bases and took doughboys’ dough with rigged games.

In 1929, Bernstein—rebranding himself “Roger O’Ryan”—staged a week-long Irish Fair in the Boston Garden, advertising “SOD FROM EVERY COUNTY IN IRELAND…HUNDREDS OF IRISH COLLEENS.” The sod was grown in Massachusetts and the colleens were local showgirls. On the fair’s final day, Bernstein took the money and ran, leaving employees unpaid. “OWNER OF IRISH FAIR MISSING,” screamed the Boston Herald’s front page. “COLLEENS CLAMOR FOR WAGES.” Soon, Bernstein—dubbed “Mr. O’Ryanstein” by the Herald—was wanted for fraud.

Any time cops and creditors closed in, Bernstein took to the sea, sailing to Europe or Asia, earning cash en route by skinning fellow first-class passengers in high-stakes card games. Upon docking, he’d search for and frequently find rubes dying to be separated from their lucre. “A guy like me should travel,” he wrote in a letter from London. “There are so many saps around, I don’t know which one to tap first.”

Bernstein spent much of the 1930s in China, calling himself “The Jade King” and selling precious stones—and dubious facsimiles—to tourists. Occasionally, he’d smuggle jade into the U.S. by feeding the jewels to Benny, his Sealyham terrier, shortly before he and the pooch strolled through customs, retrieving the stones when Benny relieved himself.

Bernstein was in Shanghai in 1934 when he conceived his notorious nickel-to-Nazis scam. He met a German diplomat who said his government was looking to buy large quantities of nickel, needed to make weapons. Bernstein claimed to have a nickel connection in Canada, which produced most of the world’s supply but had barred the metal’s export to Germany. The diplomat suggested Bernstein meet an official at the German embassy in Washington. In 1935, Bernstein visited the fellow, bringing samples of high-grade nickel he’d bought at a shop in Manhattan. Impressed, the bureaucrat dispatched Bernstein and his samples to the Fatherland, where Nazis gave him $1,000 as a down payment on an order of 225 tons.

Setting his trap, Bernstein told his customers that, to avoid the embargo, the shipment would come labeled “scrap metal.” Then he found a crooked Canadian junkman. Together, the pair gathered 225 tons of scrap and a smidgeon of nickel, bribed an inspector to certify that the load was 99 percent nickel, and shipped it all to Germany, collecting nearly $150,000. It was, biographer Shapiro wrote, “the grandest racket of his career.”

Fearing the inevitable indictment, Bernstein fled to China but when he returned to Los Angeles in 1937 to sell jewels, the cops nabbed him. He spent seven weeks in jail then went free on bail. After years of legal wrangling, the charges were dropped in June 1941.

Seven months later, Bernstein was on his way to meet with a Hollywood producer when he suffered a fatal heart attack.

“When I die,” he’d bragged years earlier, “no matter where I go, you can gamble that I will pick up a little coin on the jump.”

This article appeared in the Winter 2023 issue of American History magazine.