Those who might be inclined to regard this month’s selection of his and her gifts for Valentine’s Day (see "Love Matches," page 88) as yet another example of our society’s coarse commercialization would do well to remember that the romantic sentiments we idealize on this particular holiday have long been trafficked in the matrimonial marketplace. In the Europe of past centuries, noble parents routinely bartered their children’s hearts and fates to gain political advantage, while in the New World, cupidity, rather than cupid’s arrows, paired off the progeny of the upper classes.
During this country’s Gilded Age, few in the matchmaking profession equaled the success of Mrs. Richard T. Wilson. The wife of a Georgia businessman who had amassed a small fortune selling cotton to the British during the American Civil War, this determined lady installed her brood in the former Fifth Avenue mansion of Tammany Hall boss William Tweed and proceeded to launch a breathtaking assault on New York’s patrician bastions. She managed to marry her eldest daughter, May, to Ogden Goelet, heir to a real-estate fortune that rivaled that of the Astors. Emboldened by this coup, she secured for her son, Orme, an Astor bride—Carrie, the youngest daughter of the Mrs. Astor of Four Hundred fame. Next, she cast an eye across the Atlantic in search of an aristocratic mate for her daughter Belle, who, in 1888, married Sir Michael Henry Herbert, brother of the Earl of Pembroke. Finally, she saw to it that her youngest child, Grace, reigned in drawing rooms on two continents as Mrs. Cornelius Vanderbilt III. The "marrying Wilsons," as the family were called, provided irresistible fodder for the tabloids, one of which observed that this industrious mother had "brought more money into her family than the original J.J. Astor or Commodore Vanderbilt had gained…. No financier in the world controls as much money as Mrs. Wilson and her son and daughters. No American matron has ever approached her record as a matchmaker."
Yet in the first half of the following century, the children of Mrs. Harvey W. Cushing would give the marrying Wilsons a run for their spouses’ money. This ambitious wife of a prominent Boston neurosurgeon assiduously groomed her three daughters to scale the social heights. Their education and upbringing emphasized good manners and poise, and one by one the young ladies—who would later be featured in Life magazine and dubbed the "fabulous Cushing sisters" by the press—made their debuts. Mrs. Cushing conducted her first experiment in hypergamy on behalf of the middle sister, Betsey, who in 1930 married James Roosevelt, the son of the governor of New York. The groom possessed no personal wealth of his own, but when his father was elected president, Betsey became the de facto White House hostess, thanks to the frequent absences of the first lady, who preferred social work to social functions. This arrangement enabled young Mrs. Roosevelt to advance her siblings. She gave a coming-out tea for her younger sister, Barbara, and she introduced her older sister, Mary, to Vincent Astor. The millionaire philanthropist subsequently invited Mary—or Minnie, as she was known—to accompany him on scientific trips to Fiji and the Galápagos Islands. In 1940, Helen, Astor’s wife of 26 years, divorced him on charges of mental cruelty, and Astor proposed to Minnie. Only a week before the nuptials, Barbara, or Babe (pictured)—undeniably the most beautiful of the three—wed Stanley Grafton Mortimer Jr., heir to a founder of Standard Oil.
Still, despite these successes, the fabulous Cushing sisters only surpassed the achievements of the marrying Wilsons during the second phase of their careers. Months before her sisters’ weddings, Betsey filed for divorce from Roosevelt and took up with John Hay "Jock" Whitney, the grandson of financier William C. Whitney and, at the time, one of the wealthiest men in America. Two years later, Whitney divorced his wife and married Betsey. In 1946, Babe ended her faltering marriage to Mortimer and, one year later, became the bride of CBS founder and media mogul William S. Paley, who had obtained a Reno divorce from his first wife. Even Minnie made a change—but one that her mother and Mrs. Wilson would doubtless have considered perverse: In 1953, she left Astor and married painter James Fosburgh for love.
