by Mark Frost
His mother, Augusta Yawkey, had married a straightlaced insurance executive named Thomas Austin, a match that pleased her conservative tycoon father, William Clyman Yawkey, the reigning patriarch of their clan. But Thomas Austin died suddenly during his son’s first year, and when Augusta proved unable to subsequently cope with the trials of single motherhood, three-year-old Tom was delivered into the care of her brother, Bill Yawkey, a notorious New York bachelor playboy. Under the category of “What were they thinking?” young Tom grew up in his uncle Bill’s Upper East Side penthouse, a madcap whirligig of dissolute socialites, degenerate gamblers, pliable showgirls, and professional wrestlers. Determined to help his wayward son find some semblance of a vocation, William Clyman Yawkey made a bid to buy the Detroit Tigers in 1903 for the baseball-obsessed Bill, but died suddenly before the deal went through. With his share of the family fortune now available to him, Bill Yawkey doubled back and made an even better deal for the Tigers, and quickly decided he had found the millionaire’s ultimate toy train. Ballplayers, he discovered, shared all of Bill Yawkey’s manly interests—hitting, pitching, hunting, drinking, and playing the field, not necessarily in that order—and with Bill writing the checks, the party never ended. A few years later, in 1907, his Tigers rewarded their owner’s largesse by winning the American League pennant and playing in the World Series against the Chicago Cubs. Yawkey enjoyed that ride so much, even though they lost in five games, that he rewarded his Tigers with Series bonuses bigger than the shares received by the winners.
When Augusta 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 stopped in 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 idea in 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 looking to get out from under their obligations, Tom Yawkey had bought himself a job—and set course on an obsessive quest for the prize that had eluded his uncle and, he declared, would give his life meaning: winning a World Series.
Yawkey landed in Boston as a complete stranger—worse yet, a lifelong New Yorker—with no connections to its cloistered, tight-knit community; New Englanders greeted him warily. To win them over and demonstrate the seriousness of his intent, Yawkey immediately began a badly needed renovation of twenty-year-old Fenway Park. The park was stripped down to its original steel frames, and out went the old wooden bleachers and the slope on Duffy’s Cliff. Yawkey ordered up a new clubhouse and state-of-the-art amenities for his players, including a bar and a bowling alley in the basement. A new thirty-seven-foot-tall metal-and-steel wall, the exoskeleton of the Monster that stands to this day, went up over the newly level left field, sporting the game’s first electric scoreboard. Pouring fifteen thousand cubic yards of concrete, Yawkey added over ten thousand new seats and an expansive press box, employing more Bostonians than any other construction project had since the Crash. Having spent well over a million dollars, he now had the far more difficult problem facing him of a complete renovation of the Red Sox roster, a team that had finished dead last in nine of the last eleven seasons.
At the first owners’ meetings he attended that winter, Yawkey stunned his conservative old-school colleagues by jumping to his feet and bluntly announcing he was in the market for top-shelf players with which to stock his new ballpark and that money was no object. The other owners, quickly getting over their shock at this impropriety, proved only too happy to help; before the week was out, Yawkey had dropped another quarter of a million on a handful of has-beens and never-would-be’s, who would contribute little to changing the Red Sox’s losing ways. An informal competition developed around the league over the next few years to see who could get the Red Sox to overpay the most for marquee names like Lefty Grove and Joe Cronin, who were past their prime. Even bottom-of-the-roster players earned more than the league average under Yawkey, who proved to be a soft touch above and beyond salary for any of his men who came to him with a hard luck story; players on other teams began calling them the “Gold Sox.” By introducing “checkbook” baseball, Tom Yawkey changed forever the way the game was played in the front office, and his hyperactive turnover of talent, perpetually chasing big names with big bucks without much regard for actual need or overall chemistry, set the mood for much of the team’s next four decades.
Another destructive team dynamic was set up by Yawkey’s spendthrift tendencies: A long line of competent field managers found themselves constantly at odds with their general manager—all three of the men who ran the team through 1960 were Yawkey cronies, who only sporadically delivered the sort of player the field manager felt he needed to win. When in 1935 he finally l
anded a future Hall of Famer still in his prime, burly slugger Jimmie Foxx, Yawkey went out almost every night after games pub-crawling with the hard-drinking first baseman. Yawkey began a tradition of taking batting practice with his boys before home games and working out with them in the field, casting himself a whole lot more as a pal than a boss. Borrowing another page from Uncle Bill’s playbook, during spring training he arranged regular visits for his team to a local brothel; decades later a tenacious reporter from the Boston Globe uncovered evidence that Yawkey may have actually owned the brothel. For any manager trying to push, mold, or discipline the owner’s grab-ass buddies, the job was virtually impossible; turnover at the position became a constant.
Although he anticipated the future of baseball by pursuing 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 city workers. 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 native and war veteran, the disciplined, dedicated O’Connell had been with the team since 1947, worked his way up through the organization, and inherited the job by default when Ted Williams turned it down after retiring in 1960. For the first time in thirty years, the Red Sox had a general manager in place who was an executive first, not just another featherbedding former player and Yawkey yes-man. By mid-decade O’Connell had revitalized the Red Sox farm system, producing the first steady stream of solid prospects the team had ever seen; and, not coincidentally, for the first time in franchise history many of them were Latin or African-American. When the first wave of these players was ready to step up to the majors, O’Connell tapped the man who’d been managing most of them at the team’s Triple-A franchise in Toronto, hard-liner and future Hall of Famer Dick Williams, to take over what had devolved into an aging, overpaid, and complacent Red Sox squad that played to crowds occasionally numbering in the hundreds. Fans derisively referred to this bunch as the “country club Sox” and like the team itself, Fenway Park had also fallen into disrepair. Far from the cherished shrine of the game it is today, with its peeling paint and broken windows Fenway was dismissed by most as a rusted relic from a bygone age. In the course of lobbying for a new, modern park in downtown Boston, Yawkey used the now familiar refrain of blaming his team’s woes on their antiquated stadium, and like owners everywhere he also wanted the city and taxpayers to underwrite it. His new manager was about to change all that.
Schooled in the disciplined Dodgers tradition, the thirty-seven-year-old Williams brought the hammer down, replacing what he correctly perceived to be deadwood on the Red Sox roster with many of his players from Toronto, and opened the 1967 season with the second-youngest lineup in either league. Everyone expected that a few seasons of rebuilding had to follow. Expectations were so low that fewer than ten thousand people turned out for Opening Day and oddsmakers calculated that the Sox were 100–1 to win the American League pennant. But with his marine drill instructor’s mouth and sharp baseball mind, Dick Williams turned his team into a contender from day one; what was known as the “Summer of Love” across America became the “Impossible Dream” in Boston, as fans hung the theme of the hit Broadway musical Man of La Mancha on their improbably resurgent Red Sox. Young outfielder Tony Conigliaro slugged fifty-six home runs in his first two seasons and had already earned matinee idol status with Boston’s female population. He was joined now by a fiery, hard-hitting shortstop from Brooklyn who quickly became another fan favorite, Rico Petrocelli. But these Sox were led on the field by the man who had replaced Ted Williams in left field in 1961 but in the minds of Boston’s demanding fans never come close to equaling him, blue-collar workaholic Carl Yastrzemski. Solid but hardly a superstar to that point in his career, Yastrzemski came of age in response to Dick Williams’s tough discipline and won the Triple Crown in 1967, leading the American League in batting average, home runs, and runs driven in; he was only the third man to pull off that trifecta since Ted Williams himself, who did it twice. Yastrzemski was named the American League’s Most Valuable Player for his efforts, but it was his performance during the season’s last two weeks that earned him a place in the hearts of Red Sox fans forever. With four teams still in the pennant race down to the wire, Yaz hit five home runs, drove in sixteen, and hit an astounding .523 as Boston won eight of their last twelve games and captured the American League pennant with a one-game lead. Tom Yawkey embraced Yaz in the clubhouse, calling it “the happiest day of my life.” Despite Yastrzemski’s continued heroics in the World Series, the Sox came up short once again, when the Cardinals’ ferocious African-American star pitcher, Bob Gibson, beat them th
ree times, and they lost in seven games.
But the memories and emotions stirred by that breathtaking pennant race had provided such a joyride it hardly seemed to matter; baseball fever had been born again in New England. The old fans who’d drifted away during the indifferent years came back to the fold, and a generation of baby boomers fell in love with this modern edition of their parents’ and grandparents’ Red Sox. During an era when clubs around both leagues tore down their charming old prewar bandboxes, putting up soulless cookie-cutter concrete “multi-use” stadiums in their place, fans also renewed their affection for the quirky, angular ballpark where their Red Sox worked and played. The “Impossible Dream” also rekindled Tom Yawkey’s ancient obsession, and between 1968 and 1975, the frayed civic image of both the ballpark and its owner underwent a complete and remarkable conversion. For all the money the Red Sox had cost him through their many lean years—by 1967 his total losses were calculated at close to $8 million—Yawkey never felt the pinch; he was worth hundreds of millions now, and against the weight of that fortune the team remained at best a minor item on his balance sheet. And as a result of their “Dream” season, from ’67 on the franchise began doing something it had never done before: making more money every year. All talk of Tom Yawkey selling the Sox, a persistent rumor in Boston for the past decade, now vanished, as did any thoughts of tearing down Fenway Park. Yawkey showed up on most game days again, an old man now but still out there in spikes and sweats playing pepper with his bat boys—he often paid for the college education of his favorites—or taking a few grounders from longtime clubhouse attendant Vinnie Orlando before games. When he shuffled into the Red Sox clubhouse, a soft-spoken, retiring figure in baggy pants and a cheap windbreaker, newcomers occasionally mistook him for an attendant himself; during their first meeting in 1974 newly acquired outfielder Bernie Carbo asked Yawkey to run out and grab him some lunch.