When Boston Red Sox owner Tom Yawkey died in 1976, he left his entire baseball empire in the care of his wife Jean. At first it appeared that she had no interest in taking his place. However, circumstances arising from internal jockeying by others to take over the ballclub led to her emergence as one of three general partners in charge of the operation. Then, following disputes over management decisions and an agonizing legal battle, she gained majority control. Her passion for baseball outweighed her stoic reserve, and she spent the rest of her life in the quest of a World Series title. That ultimate prize remained as elusive to her as it had been to her husband. Nonetheless, she came to be known as the most powerful woman in baseball history.
Because she valued her privacy and avoided interviews, details of Jean Yawkey’s early life remain somewhat vague. Much of what is known we owe to the journalistic efforts of Susan Trausch of the Boston Globe. In an enlightening piece titled “The Woman Who Owns The Red Sox Keeps Her Private Life Private,” Trausch provides important biographical details.1
Born in Brooklyn, New York on January 24, 1909, Jean Remington Hollander was “raised in the village of Freeport, N.Y. on Long Island.”2 Although the identity of her parents remains uncertain, it is known the she had an older brother George. Jean graduated from Freeport High School in 1926. The editor of the school’s paper, she once took honors in its annual public speaking contest. Following graduation, she married Charlie Hiller, the former star of Freeport’s basketball team. The marriage was short-lived, ending either in divorce or when Hiller died. Then, for more than a decade, Jean made a living as a model and salesperson at New York City’s exclusive women’s clothing store, Jay Thorpe. A striking, statuesque brunette with dark brown eyes, her innate air of refinement served her well. Legend has it that she met Tom Yawkey at Jay Thorpe when he was shopping there with his first wife Elise.3
Nowhere is it said that Jean Hollander broke up Tom Yawkey’s first marriage. It is clear that that union was troubled. The two had been separated for three years before Elise filed for divorce in Reno in November 1944. The following month on Christmas Eve, Tom and Jean (then Jean Hiller) were married in a private ceremony in Georgetown, South Carolina where Tom owned a home and a large expanse of land. Trausch writes that at their wedding they were dressed in “their hunting clothes, casual pants and tops, much more like L.L. Bean than Jay Thorpe.” This and other evidence points to Jean’s persona as quite the opposite of that of Tom’s first wife Elise, a socialite of the first order. Jean was more of an outdoors person, and gravitated toward a simpler way of life. Although Tom owned a mansion elsewhere in the Georgetown area, he and Jean preferred to live in a relatively modest beach lodge on the South Island property during the offseason.
Born in Detroit in 1903, Tom Yawkey was raised by an uncle after his father died. Uncle Bill Yawkey once owned the Detroit Tigers. That no doubt contributed to Tom’s lifelong love for the sport of baseball. In 1933, after his college years at Yale, and on attaining his 30th birthday, Tom seized the opportunity to use his substantial inheritance to purchase the Boston Red Sox. After he married Jean, it became obvious that she shared his baseball zeal. Compatible in other ways too, the couple did not gravitate toward the social set. During the baseball season they lived in a suite at Boston’s Ritz-Carlton Hotel. Then their activities centered on the Red Sox. After a game at Fenway, they would immediately return to their hotel where they often entertained ballplayers and close associates.4
In time, Mrs. Jean Yawkey became a fixture at Boston’s Fenway Park. She rarely missed a Red Sox home game. She and Tom sat in separate rooftop boxes because she disliked hearing him cuss with his pals. Her attention always on the game, she shared her box with trusted friends. Chain smoking and often sipping on a martini, her trusty binoculars on hand, she meticulously recorded each play of each inning in a specially-bound score book. Interestingly enough, her penchant for scorekeeping mirrors that of the first woman owner of a major-league team, Helene Britton, onetime owner of the St. Louis Cardinals. Moreover, Joan Payson, the original owner of the New York Mets devised her own complex method for game tallying.
Although a pall remained over the Red Sox organization owing to the fact that it was the last major-league team to integrate, Tom Yawkey was well liked by most who knew him. Many of the players looked on him as a father figure. He and Jean had no children of their own, so one could say the Red Sox became their family. Sadly, more than 30 years after they wed, Tom was diagnosed with leukemia. Boston fans and players alike were heartbroken when he died on July 9, 1976. He left his baseball holdings to a trust controlled by his widow. Tight lipped about her plans for the ballclub, Jean Yawkey finally issued a brief statement in April of the following year. It simply said that offers to purchase the Red Sox would be accepted.
On September 29, 1977, it was announced that an agreement had been reached for an estimated $15 million. The group making the offer was headed by former Red Sox backup catcher Haywood Sullivan and the club’s former trainer Buddy LeRoux. The plan placed Mrs. Yawkey in the background as a limited partner. But before the other American League owners could approve the proposition, she exerted her authority by firing the club’s general manager Dick O’Connell and two of his aides. Haywood Sullivan was named as O’Connell’s replacement.
O’Connell was undoubtedly more than competent in his job. Tom Yawkey hired him years earlier, and had every confidence in him. But, for whatever reason, Jean Yawkey did not like the man. Reports of the time reveal that she had not spoken to him for several years before Tom’s death. O’Connell was probably not the first, and definitely was not the last person to be the target of Jean Yawkey’s silent treatment. She replaced him with Haywood Sullivan, who had become somewhat of a surrogate son to her. Hired by O’Connell as director of player personnel in 1966, Sullivan eventually gained status as one of the few people invited to sit with Mrs. Yawkey in her rooftop box. So it seems that in addition to O’Connell’s alienation of the deceased owner’s wife, his dismissal may have also been fueled by something akin to nepotism.
Not long after the firings, the AL rejected the sale proposal. Then, when A-T-O Corporation of Ohio tried to force a sale with a bid of $18,750,000, Mrs. Yawkey stepped in and supplemented the Sullivan/LeRoux tender. Her contribution of Fenway Park upped it to $20.5 million. The value of the ballpark accounted for the increase. She also lent money to Sullivan and LeRoux so that they could avoid bank loans, which had been one of the league’s main concerns. The final agreement named three general partners: Sullivan, LeRoux, and Mrs. Yawkey. Nine investors were limited partners, Mrs. Yawkey included. She was both a general and a limited partner. To manage her holdings, she formed the trust JRY Corporation, becoming its president and sole stockholder.
In May 1978, the AL owners approved the group’s revamped bid. The new ownership retained Sullivan as general manager and named LeRoux vice-president, administration. Mrs. Yawkey served the role of team president. The three general partners wielded the power, but the limited partners were to collect a major share of the profits until their investment was returned with interest.
During the changes in management, the Red Sox continued playing over .500 as they had since 1967. But when they dropped to fifth in the AL East in 1980, Sullivan and LeRoux decided to fire manager Don Zimmer. Mrs. Yawkey vehemently opposed the move. This perhaps precipitated the distance that developed between her and Sullivan. The two continued to maintain something of a filial relationship, but they often butted heads in matters of hiring and firing. She apparently viewed his every disagreement as disloyalty. Another factor that came into play was her desire to continue operating the Red Sox in her husband’s tradition. To her, building a winning club took priority over increasing revenue. Free agency had just come into being when Mrs. Yawkey took over, so that placed a new dimension on such a practice. It likely did not sit well with her when in 1981 the club lost its most popular player to the White Sox due to Sullivan’s negligence. He mailed prized catcher Carlton Fisk’s contract two days after the deadline.
Most of what is known about Jean Yawkey during her ownership years is based on observations by reporters, business associates, and Red Sox players and staff. She shunned interviews and public speaking. She even declined to speak at Cooperstown at her husband’s induction into the Hall of Fame in 1980. That might lead to the belief that she was unapproachable and coolly detached. However, her acquaintances attributed that demeanor to shyness. Some said that she had a great sense of humor and a loud, hearty laugh. She was also known to engage in warm conversation with fans, ballplayers, and Red Sox staff members. But when approached by the media, she would clam up. That’s what made her willingly, if reluctantly, taking the spotlight during a nasty power struggle in 1983 so significant. At that time her indomitable strength of will prevailed.
A contentious relationship among the new owners existed from the start. LeRoux and Kentucky coal mine owner Rodgers Badgett, the limited partner with the largest investment, focused primarily on padding the profits. They even cut back on team and fan amenities. Because of her free-spending style, Mrs. Yawkey strongly disapproved of such tactics. Probably hoping to control an empire of his own, LeRoux made a failed attempt to buy the Cleveland Indians sometime early in 1982. Then, in May of the next year, Boston TV executive David Mugar made a substantial offer for LeRoux’s and Badgett’s shares in the Red Sox. Citing right of first refusal, Mrs. Yawkey and Sullivan prevented that deal from materializing. They had no quarrel with Mugar, but they wanted to purchase those shares at “fair market value” themselves. So they proposed eliciting an appraisal. By this time Mrs. Yawkey was no longer on speaking terms with LeRoux. The breaking point came when Badgett criticized her in a memo. Highly insulted, she blamed LeRoux. Finally, the former team trainer made a move that both bewildered and offended Red Sox nation.
On June 6, 1983, reporters gathered at Fenway anticipating the scheduled Tony Conigliaro Night, an event meant to benefit the former player hospitalized by a stroke. Taking advantage of the assembly, LeRoux called a press conference and made a startling announcement. He proclaimed that the majority stockholders were taking control of the Red Sox. That majority included himself, Badgett, and Boston attorney Al Curran. He rationalized that his investment as general partner coupled with Badgett’s and Curran’s limited partner shares outweighed all other interests. Naming himself managing general partner, he declared that the deposed Dick O’Connell would replace Sullivan as general manager. Choosing to engage in such histrionics just as Red Sox fans prepared to honor a fallen hero was tactless to say the least.
As the ballclub staff tried to make sense of the declaration, John L. Harrington, representing Mrs. Yawkey, and Sullivan took LeRoux’s place at the conference table. Harrington declared that the majority of the three general partners ruled, and that there would be no change in command. Regardless of Sullivan’s differences with Mrs. Yawkey, this was a situation that placed him solidly on her side. LeRoux’s action was temporarily blocked by a court order, and the dispute went to trial.
In July, the case was heard by Judge James P. Lynch at the Suffolk County Courthouse. Although Harrington did most of the testifying on behalf of both Sullivan and JRY, on Wednesday, July 13, Mrs. Yawkey took the stand herself. Boston Globe reporter John Powers described her there for two hours “in her tinted glasses and simple checked pantsuit.”5 Though not at all comfortable in this fishbowl setting, she held her ground, responding to questioning with terse directness. She grew indignant when the defense counsel spoke with his back to her. “I do not understand you when you walk away from me,” she charged. Few people realized before then that she suffered from a hearing problem. That physical deficiency undoubtedly contributed to her seeming reticence. And although she was subjected to some ridicule during the court ordeal, she ultimately won out.
In August, the court ruled the June 6 attempted takeover illegal, and “permanently enjoined and restrained” LeRoux from any future such attempted coup. It also held that if he wanted to sell his share, it must be offered to the other two general partners first. In one of her rare statements to the press, Mrs. Yawkey simply said “I’m very pleased,” adding, “It hasn’t been pleasant.”6 She went on to suggest that the partnership would continue as before. Nonetheless, she had gained new respect, refuting the notion that her shyness and hearing difficulty equated to weakness. The unpleasantness of the situation only served to toughen her, and she emerged as a person of note in the world of big-league baseball.
In 1984, Jean Yawkey was elected a member of the Board of the National Baseball Hall of Fame and Museum. She was the first woman to achieve that position. That same year, Lou Gorman came over from the Mets, replacing Sullivan as the Red Sox GM. The owners’ squabble had arguably taken its toll on the Boston club. During the year of their court battle, the team’s won/loss record dropped below .500 for the first time in nearly two decades. Gorman got it back on track, staying with the Red Sox for the remainder of Jean Yawkey’s ownership years.
The enigmatic Mrs. Yawkey exhibited true class when in 1986 her beloved Sox came within a strike of capturing her’s and Tom’s long sought-after World Series title. When Buckner’s error led to the club’s devastating loss, though sorely disappointed she remained composed and almost philosophical. Several years later, Rico Picardi of Harry M Stevens, Inc, the Fenway Park concessionaire and a Red Sox limited partner recalled that at the time she was consoling everyone else. He said that with tears rolling down her face she said, “We got beat fair and square and there was nothing to be ashamed of.”7 The following year, she bought out LeRoux for an estimated $7 million, giving her two votes to Sullivan’s one, effectively full control of the Red Sox. She also named Harrington, who by then had become her closest confidant, president of JRY Trust.
Against Sullivan’s wishes, in 1988 Mrs. Yawkey fired manager John McNamara and gamely took the heat when criticized for the timing. Although Harrington was her chief spokesperson, he made it clear that Mrs. Yawkey was the one running the Red Sox. He once told Boston Herald reporter Tim Horgan that “…the buck stops with Jean.”8 By 1990, her relationship with Sullivan had deteriorated to the point that the two no longer spoke. Unlike those with others, her dispute with him was more akin to a family feud.
Although Boston won the division title in 1988, and again in1990, Mrs. Yawkey didn’t live to see her dream of a World Series title realized. On February 20, 1992, she suffered a stroke at her Four Seasons Hotel condo in Boston where she had lived alone since 1987. Found by a hotel employee who checked on her when she failed to come down for her morning paper, she was rushed to Massachusetts General Hospital. The 83-year-old baseball owner died there six days later. Her passing marked the conclusion of an era - the era of the Yawkey way.
Tributes to the departed Red Sox owner flooded the news. Such designations as Red Sox “grande dame” and “matriarch” conveyed the high regard held by New Englanders for Mrs. Yawkey. To some Boston residents she was “the soul of the city.”9 Unlike her female contemporaries, the bombastic, miserly Cincinnati Reds’ Marge Schott and Padres figurehead Joan Kroc, Jean Yawkey was joined with her ballclub family till death. Having a generous nature, she paid and treated her employees well. Credited with keeping her “house” habitable, she prevented venerable Fenway Park from falling prey to the modern feeding frenzy that consumed so many of its counterparts.
In addition to her ballpark, the Baseball Hall of Fame in Cooperstown holds lasting evidence of Mrs. Yawkey’s devotion to baseball. In 1990, she bequeathed a $1.5 million grant for the expansion and further development of its library. Five years earlier, she had commissioned sculptor Armand LaMontagne to do the remarkably lifelike basswood statue of Ted Williams for the museum. Also, her philanthropic endeavors are legendary. She particularly favored the Jimmy Fund of the Dana-Farber Cancer Institute, the official Red Sox charity.
A number of non-profit groups in New England and South Carolina received support from Mrs. Yawkey’s JRY Trust. On May 15, 1988, she was honored “for her lifetime of community service” at Boston’s Symphony Hall.10 That night she graciously accepted a newly established award named for her, the Jean R. Yawkey Award. An organizer of the event observed that she was delighted with the big turnout, and later stayed and talked with people outside on the street.11 Stories such as this counter her reputation as the Greta Garbo of sports.
The most telling tributes to Mrs. Yawkey were reactions to her death by active and retired Red Sox players. Revered slugger Ted Williams was said to be “hit hard by the loss of a friend.”12 Fellow HOFer Carl Yastrzemski, equally saddened by her death, told how much both the Yawkeys had meant to him. Then-current backup catcher John Marzano’s statement to the Boston Herald reflected the feelings of many of his cohorts: “It’s really sad – she was such a good person…everybody on the team will miss her.”13 He then reflected, “Here I am a guy who plays once a week, and every time she’d see me she’d say ‘John, you’re doing a great job, keep up the good work.’ She was always nice to me.”
On Friday, February 28, 1992, the ashes of Jean Remington Yawkey were ceremoniously spread over Winyah Bay at Georgetown, South Carolina Her husband Tom’s had been distributed there near the Tom Yawkey Wildlife Center 16 years earlier. Years before that, the couple’s initials, TAY and JRY, had been printed in white Morse code on the out-of-town scoreboard at Fenway Park. During the 1992 season, the Red Sox wore the initials JRY on their uniform sleeves in honor of Mrs. Yawkey. Three years later, she was inducted into the Boston Red Sox Hall of Fame.
Following Mrs. Yawkey’s death, John Harrington controlled the Red Sox as president of JRY Trust. In 1993, the corporation bought out Sullivan’s one-third share for $12 million. Eight years later, a group led by John W. Henry bought it all for $700 million with the proceeds going into a trust to benefit the numerous non-profit organizations that Jean Yawkey had favored. That truly marked the end of an era.
Stories about Jean Yawkey reveal that she enjoyed reading mystery novels.14 Yet her life remains somewhat of a mystery. In the dozens of print tributes to her in 1992, none named any living relatives. Some seven years later, the news surfaced that her nieces had questioned the contents of her will. The two daughters of Jean Yawkey’s brother George, who died in the 1970s, Patricia Hollander and Jane Esopa, believed that Harrington purposely left them out of the loop. The Long Island sisters, as well as Esopa’s three daughters, each received a small sum from an insurance policy - but nothing more. They contended that not only did Harrington not inform them of Mrs. Yawkey’s stroke (they heard about it on the news), but that he also failed to include them in the Georgetown memorial service. Harrington dismissed their charges with polite denials. Several news items suggest that the nieces’ limited finances prevented them from pursuing the matter further. Why they did not benefit from their aunt’s sizable fortune leaves room for all sorts of speculation. The truth may never be known.
There are those who believe that even during Jean Yawkey’s years as owner, it was John Harrington who controlled the Bosox. Still, one only need note how her relationship with LeRoux, and then Sullivan soured. When they went up against her wishes, she shut them out. O’Connell too found himself a casualty of her ire, likely for similar reasons. So that would leave Harrington as either a master manipulator or simply one who followed orders without question. Perhaps the truth lies somewhere in between. All mysteries aside, Jean Yawkey’s legacy remains intact. The Boston Red Sox and Fenway Park live on.
An updated version of this biography appeared in "The 1986 Boston Red Sox: There Was More Than Game Six" (SABR, 2016), edited by Bill Nowlin and Leslie Heaphy.
Bodley, Hal. “Very private Yawkey stuck by her Red Sox,” USA Today, February 27, 1992.
Farmelant, Scott. “Boss Harrington,” Boston Magazine, June 1996.
Gammons, Peter. “Court upholds Sullivan, Yawkey,” Boston Globe, August 11, 1983.
Horgan, Sean. “End of a Red Sox era,” Hartford Courant, February 27, 1992.
Horgan, Tim. “Make no mistake: Yawkey’s in charge,” Boston Herald, July 31, 1988.
Horgan, Tim. “Mrs. Yawkey Takes Over as Red Sox Angel,” Boston Herald. March 18, 1978.
Krause, Steve. “Yawkeys ran Red Sox with class, integrity,” New England Newsclip Agency, Inc. February 27, 1992.
Murphy, Joe. “Mrs. Yawkey, we’ll miss you.” New England Newsclip Agency, Inc., February 27, 1992.
Powers, John. “Bosox’ brouhaha brings Jean Yawkey to stand,” Boston Globe, July 14, 1983.
Trausch, Susan. “The Woman Who Owns The Red Sox Keeps Her Private Life Private,” Boston Globe, April 6, 1989.
Whitney, George. “Fans’ Passion For Team Surpassed Only By Mrs. Jean Yawkey’s,” Diehard, March 1992.
“A night to honor Mrs. Yawkey,” Boston Herald, May 22, 1988.
“Jean R. Yawkey Inducted Into The Boston Red Sox Hall Of Fame,” Boston Red Sox press reelease, September 25, 1995.
“League Approves Sale of the Red Sox,” The New York Times, May 24, 1978.
“Owners give approval to Sox sale,” North Adams Transcript, May 24, 1978.
“Red Sox heirs in inheritance battle,” New York Post, March 19, 1999.
“Yawkey Grant Of $1.5 million To Aid HOF Library Expansion,” Hall of Fame News Release, Sept. 28, 1990.
Pacific Stars And Stripes, February 28, 1992.
Syracuse Herald-Journal, July 13, 1999.
Berkshire Eagle, October 25, 1977.
The New York Times
The News (Frederick, Maryland)
Albany Times-Union, New York
1 Susan Trausch, Boston Globe, April 6, 1989.
3 New York Times, February 27, 1992.
4 Both the Susan Trausch article and one by David Cataneo in the Boston Herald. February 27, 1992 say that the Yawkeys sometimes entertained players there, but this is not something we have been able to verify.
5 Boston Globe, July 14, 1983.
6 “Court upholds Sullivan, Yawkey,” Peter Gammons, Boston Globe, August 11, 1983.
7 “A night to honor Mrs. Yawkey,” Boston Herald, May 22, 1988.
8 “Make no mistake: Yawkey’s in charge,” Tim Horgan, Boston Herald, July 31, 1988.
9 “Fans mourn loss of ‘the soul of the city’” Kathryn Marchoki, Boston Herald, February 27, 1992.
10 Invitation to Jean Yawkey Night at the Pops, May 15, 1988.
Note: The Colonel Daniel Marr Boys and Girls Club of Dorchester and The Massachusetts Association for Mental Health sponsored the event…The New England Council of Women Professionals established the award.
11 Susan Trausch, Boston Globe, April 6, 1989.
12 “Williams hit hard by loss of friend” Dan Shaughnessy, Boston Globe, February 27, 1992.
13 “Baseball world mourns death of Sox matriarch” Steven Solomon, Boston Herald, February 27, 1992.
14 Susan Trausch, Boston Globe, April 6, 1989 and “A night to honor Mrs. Yawkey,” Boston Herald, May 22, 1988.