The Woodwards: Tragedy in High Society

At some point in 1942, William Woodward Sr. passed the 27-year-old Ann on to his son, five years her junior. It was love at first sight and very quickly the two were wed.

While her son's marriage started off happy, Elsie Woodward, the socialite who ran the most exclusive parlor of the New York 400, saw her new daughter-in-law as a gold digger who latched on to her son merely to get her hands on his $10 million fortune. Elsie considered Ann far below her in class and social skills and never accepted her into the family.

The Duchess of Windsor

Years later, Elsie, then the dowager empress of New York high society, talked to friends about her relationship with Ann. She recalled the first time she saw the beautiful model/radio actress. Ann was too pretty, too voluptuous to be a good person, she thought.

"One look and I knew the whole story," Elsie told her friends.

Elsie's scorn was palpable and soon the Vanderbilts and Astors and the rest of the pearls and party gown crowd who attended Elsie's parties picked up on it. Their rejection only served to fuel Ann's drive to gain acceptance. "She had no innards, no inside," a psychiatrist who treated Ann told author Susan Braudy. "All she wanted was to be Woodward."

Billy's sisters also froze off Ann. Even though she had been famous in her own right — her work on radio had gained the notice of The New York Times — she was too gaudy and flashy for their tastes. She once made the unforgivable faux pas of wearing red shoes with a blue dress and was seen smoking in public long before such behavior was tolerated in their circles.

There was only one woman in high society who ever really accepted Ann and that was because she was in a similar position. The woman was Wallis Simpson, the Duchess of Windsor. Simpson, of course, was the American divorcee for whom Edward stepped down from the throne of Great Britain to marry.