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Grace Kelly Married Into Royalty, But Her Family Couldn't Keep Their Act Together

Updated August 13, 2021 148.8k views10 items

Grace Kelly was a Hollywood starlet who walked away from the spotlight to marry into royalty. As the pinnacle of beauty and style in the mid-twentieth century, Grace Kelly became a 1950s film star after appearing in movies like Rear Window (1954) and To Catch a Thief (1955) and even won an Academy Award for her role in The Country Girl (1954).

Everything changed when Grace Kelly met Prince Rainier III of Monaco in 1955 and, when they married the following year, she started a new life as Princess Grace of Monaco. Leaving acting and the US behind, Grace Kelly wasn't able to escape everything from her past, however. The Grace Kelly family tree was always lurking in the background. From the role her family played in her nuptials — paying a massive dowry just for the marriage to proceed — to the scandalous sexual relationships that characterized Grace Kelly's family history, the reality of her family life was often anything but the glamorous fairy tale it was thought to be. 

  • Her Oldest Sister Peggy Died Of Alcoholism After Her Teenage Daughter Ran Away

    Grace Kelly's older sister, Margaret — who went by Peggy — suffered through two failed marriages, first to George Liddell Davis, Jr. and then to Eugene Conlan.

    Margaret had two children with Davis, twin girls named Margaret and Mary Lee. In 1963, 15-year-old Mary Lee ran away with her 18-year-old boyfriend, John Paul Jones, Jr. The two ended up in Des Moines, Iowa where Mary Lee worked as a waitress. They got married although Margaret didn't attend the wedding. Margaret (Kelly Davis) Conlan died of alcoholism in 1991.

  • Photo: Unknown / Wikimedia Commons / Public domain

    Her Father Competed In The Olympic Games As A Way To Disprove Haters Who Decried His Irish-Catholic Background

    Grace Kelly's father, John B. Kelly, Sr., was a self-made millionaire and a former world-class rowing champion. His determination and success was in spite of being discriminated against for his working-class Irish Catholic family line. When John, Sr., known as Jack, tried to compete in the prestigious Henley Royal Rowing Regatta in 1920, he was turned away because he "he had worked as a bricklayer and was, therefore, by lofty British standards, not a gentleman." The fact that he was Irish Catholic did not help his cause either.

    Jack's rejection was highly publicized and, while he had already decided against competing in the 1920 Olympics, he changed his mind. He told the media "I had made all the arrangements to sail for England… I’ll go to the Olympics now for sure. I want to get a crack at the man who wins the diamond sculls." Jack went on to compete in the 1920 Olympic Games in Belgium and again at the 1924 games in Paris, earning three Olympic medals. 

    Jack's brother, George, the Pulitzer Prize-winning playwright, went the other direction on how he handled his background. He chose to hide his roots and George was ashamed of his poor family, of being one of ten children, and that his education ended in the fourth grade. To make up for it, he "invented any number of fictions to conceal the truth about his upbringing."

  • Her Uncle George Had A Secret Male Lover Who May Have Blackmailed Him

    George Kelly met his long-time companion, William Weagley, when Weagley was most likely working as a bellhop. His relationship with Weagley, who was described as "a slightly built, plain-looking, unsophisticated, high school educated (the commercial course) lonely small-town book-keeper," was a blend of servant and partner, with Weagley often preparing meals and tending to Kelly. The two were fairly open with their relationship, although Weagley was often called Kelly's valet when they were together in public.

    The LGBTQ+ taboo at the time is starkly apparent when one takes into consideration what resulted from another relationship Kelly had with a bellhop prior to that with Weagley. Somehow, Kelly ended up paying for the man's education, possibly in some sort of blackmail-type context. 

  • Her Uncle Walter Was A Successful Actor Until His Sudden Death

    Grace Kelly wasn't the only actor in her family. Her playwright uncle George dabbled in acting but her father's other brother, Walter, was a successful vaudeville performer during the 1920s and 1930s. Walter C. Kelly starred in 1935's The Virginia Judge and 1936's The Tugboat Princess but, after a car accident in 1938, returned to Philadelphia where he died of injuries he'd received the following year. According to some accounts, he was broke, despite his success as an actor. Jack Kelly's sister, also named Grace, had wanted to be an actress but passed in her twenties.