Yawkey died during the influenza epidemic of 1918, Uncle Bill legally adopted his young ward, rearranging his name from Thomas Yawkey Austin to Thomas Austin Yawkey. But Bill Yawkey would follow his sister in death less than a year later, not long after he and Tom had set out on a motoring trip across the country to celebrate Tom’s sixteenth birthday. They had just stoppedin Georgia to visit Bill’s closest friend on the Tigers, legendary outfielder Ty Cobb, when Bill was stricken with a virulent pneumonia. He died days later in his famous friend’s arms, but not before extracting a promise from Cobb that he would help look after Tom after he was gone. Bill’s stake in the Tigers was sold off by his estate’s conservators—for considerable profit—but Ty Cobb kept his word, serving as a substitute foster father to young Tom. The fiercely aggressive, and probably sociopathic Cobb thus became the second of Tom Yawkey’s dubious male role models.
Now the presumptive heir to both his mother’s and uncle’s shares of the Yawkey fortune, Tom moved on to Yale, and got down to seriously pursuing the around-the-clock cocktail-hour lifestyle he’d learned from Uncle Bill; he came closest to applying himself academically when he played some second base for the Bulldogs baseball team. He also ended up in the vanguard of a tumultuous cultural revolution: GIs returning from World War I tours of duty in Paris and other European capitals had brought home with them an appetite for more sophisticated sin; tastemakers and advertisers capitalized, and young Americans following their lead threw aside the lingering puritanical inhibitions of the nineteenth century with a vengeance. The last gasp of the Victorian generation’s crusade to stamp out the evils of hedonism came in 1919: a misguided constitutional amendment called the Volstead Act, better known as Prohibition, which outlawed the production and distribution of alcohol. Free, filthy rich, and twenty-one, openly scoffing at Prohibition, Tom Yawkey was frequently singled out in the press as a standard-bearer for this “Roaring Twenties” generation. A few years later Tom married a Jazz Age icon, a legendarily alluring dancer and beauty queen named Elise Sparrow, who had once posed for a famous portrait as a “flapper,” the era’s signature party girl. During the rest of the decade, their sybaritic life drifted hazily between a Park Avenue penthouse, the old family manse in Michigan, and a sprawling rural estate in South Carolina, stocked with game birds and deer for Yawkey’s frequent hunting trips. During one of the many stag retreats they spent together there, his mentor Ty Cobb planted the ideain Yawkey’s head that, just as his late uncle Bill had, Tom might find his calling—and prove to his disapproving trustees he could make money as well as spend it—in the ownership of a major-league baseball club. On another hunting trip the following year, Yawkey received something a lot less welcome from his old friend: a brutal alcohol-fueled one-sided beating—sudden acts of violence being just one of Cobb’s misanthropic tendencies—that abruptly ended their relationship.
The Jazz Age ended just as suddenly not long afterward, but 1929’s catastrophic stock market implosion hardly dented the Yawkey family’s commodity-based businesses. As his thirtieth birthday approached, the age when the trust stipulated that control of his fortune would pass into his hands and instantly make him one of the fifty wealthiest men in America, Tom Yawkey remembered Cobb’s advice. When he got word that Boston’s American League franchise was in play, Yawkey swooped in and snapped up the Red Sox during the darkest hour of the Great Depression. Like much of the rest of the country, America’s national pastime, and the Red Sox and Fenway Park in particular, had fallen on hard times. For the first time in his life, when many of baseball’s owners were either scraping by or actively