big-name stars without much regard for cost, Yawkey was slow to react to the most important changes the game would experience over the next twenty years. During the first four decades of professional baseball’s existence, major-league teams had relied on the inexact science of scouting and a loosely defined “regional rights” system to find and sign young players. In the 1920s general manager Branch Rickey of the St. Louis Cardinals, lacking the funds to compete for expensive talent, decided to buy a series of minor-league teams all over the country—and the rights to all the players he then placed on their rosters—thereby controlling and streamlining the process of developing future major leaguers. When this revolutionary innovation produced a roster that resulted in five National League pennants between 1926 and 1934 for the Cardinals, every other team in the majors quickly adopted the same business model. With Tom Yawkey’s mind fixed on chasing established major-league stars, the Red Sox were one of the last to assemble what Rickey had called an effective “farm system.” They were the third to last team to add lights and schedule night games, the prevailing social trend as America’s game transitioned from its pastoral daylight roots to a primary form of evening entertainment for industrialized inner cityworkers. Then Yawkey missed the game’s next great sea change by a mile: After Jackie Robinson broke the color barrier in 1947, the Red Sox were the last major-league team to sign African-Americans—passing up players like the great Willie Mays and Robinson himself, who had been treated shabbily by team officials during a workout at Fenway and forever held a grudge against the Red Sox. As a result Yawkey’s Red Sox became the last major-league franchise to field a black player in their everyday lineup—second baseman Elijah “Pumpsie” Green, twelve years later, in 1959, a hard-to-justify reluctance that raised enduring and legitimate questions about Yawkey’s racial politics.
Off the field, as he entered middle age, Yawkey’s personal life came untethered; he never showed much interest in his only child, an adopted daughter, and he periodically lost his running battle with alcohol. His marriage to Elise had quietly died years earlier, but it ended legally with a Nevada divorce in 1944; she remarried in less than a month, and a few weeks later, just before Christmas, Tom Yawkey married the woman whom he’d been quietly seeing for over three years, Jean Hiller, an attractive, younger model whose interests, in sports and the outdoors—and pleasing her wealthy husband—more closely matched his own. Unlike the independent, socially ambitious Elise, Jean Yawkey doted on her husband, and for the first time in his life he found some measure of domestic stability. But the World Series title he craved continued to elude him. The Red Sox didn’t win their first American League pennant for Yawkey until 1946, then lost that World Series in seven games to the St. Louis Cardinals, the only time the first great star to emerge from Boston’s farm system, Ted Williams, would ever play in the postseason. The team wouldn’t deliver Yawkey a second pennant for twenty-one more turbulent years. During that long stretch, although he continued to profess that he wanted to win, it became increasingly difficult for New England’s die-hard fans to believe their team represented more to its owner than a big, shiny plaything that only intermittently captured his interest.
By the early 1960s, as the Red Sox continued to tread water,Yawkey had largely become an absentee owner. He had never bought a home in Boston, operating instead out of his suite at the Ritz-Carlton and preferring to base both his business and personal life in New York and on his forty-thousand-acre coastal estate in South Carolina. That left most of the chores of running the club to the Sox’s fourth general manager, Dick O’Connell. A Massachusetts
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