Elaine Steward: 30 years later, first female assistant GM reflects on making history with Red Sox

By Gordon Edes
Elaine Steward at 2019 Winter Weekend

Elaine Weddington Steward was 26 when she became assistant general manager of the Boston Red Sox, the first woman in Major League Baseball ever to be promoted to that position, and only the second African-American.

That moment, in 1990, was recognized for what it was—historic—and Bob Watson, for one, expressed the confidence that it was a portent of more to come.

''It’s obvious that barriers are coming down,’’ said Watson, who in the course of a 19-year big-league career once played for the Red Sox, became the first African-American to be named an assistant GM and ultimately went on to sit in the big chair, first with the Houston Astros and then with the New York Yankees, who in 1998 made Watson the first African-American GM to win a World Series. Watson died in May at the age of 74.

But in truth, those walls have been slow to tumble. Last December, the Red Sox promoted Raquel Ferreira to executive vice president/assistant general manager. Ferreira is only the third woman since Steward to ascend to that position, joining Yankees assistant GM Jean Afterman and Kim Ng, who was an assistant GM with the Yankees and Dodgers before taking an executive position in the commissioner’s office. Ng interviewed for several GM vacancies, but no woman has yet to become a GM.

Out of 30 teams, there are currently four minority heads of their teams’ baseball operations: Detroit Tigers general manager Al Avila; San Francisco Giants GM Farhan Zaidi; Chicago White Sox executive vice president Ken Williams; and Miami Marlins president of baseball operations Michael Hill.

Work to be done? “Quite a bit,’’ said Steward, who is now in her 32d year and ranks as one of the longest-tenured members of the Red Sox front office, having first joined the Red Sox legal department in 1988 before general manager Lou Gorman named her his assistant two years later.

Steward’s 12-year run as assistant GM under first Gorman and then Dan Duquette ended when the club was sold in 2002, but she still deals with a host of issues, primarily on the business side, as the club counsel.

“Unfortunately, I thought things would have moved along more than they have,’’ Steward said in a recent Zoom conversation. “In terms of baseball, there are a lot fewer African-American players as well. It’s kind of sad to me there are so few players right now. There’s definitely work to be done.

“Why hasn’t it happened? I don’t know, but I feel like we’re entering into an era in which hopefully certain issues of racial equity and gender equity will be addressed more openly and examined. Hopefully, this will be the time things will move forward.’’

And when that day comes, Elaine Steward’s improbable journey to ground-breaking pioneer should be celebrated and retold. It starts with being a helpful neighbor and babysitter, and involves one of the more momentous rain delays in baseball history.

Elaine Steward grew up in Queens, a short subway ride from Shea Stadium, home of the Mets. It was a banner day in the neighborhood when a Mets player, Felix Millan, moved in next door. It certainly didn’t go unnoticed by 13-year-old Elaine.

“Everyone was so excited that a Mets player was moving in,’’ she said.

“I went up to his apartment and offered to help, taking down some of their moving boxes.

“Eventually we became very friendly. And I started babysitting for his kids.”

Curious about her new employer, Weddington began to watch Mets games on TV, and became hooked. And it was while watching during a rain delay that Weddington learned of an opportunity that would alter the course of her life. Mets broadcaster Ralph Kiner was interviewing Bernie Beglane, the dean of athletic administration at St. John’s University, about an eight-week seminar sponsored by the Jackie Robinson Foundation that came with a potential scholarship to study athletic administration.

“At that point, I had never heard of working in sports as a career, right?” Steward said. “It was just fascinating to me. So, I attended the seminar, and I was lucky enough to have earned one of those scholarships by the Jackie Robinson Foundation.”

While at St. John’s, Steward landed a part-time job as a hostess in Shea Stadium’s Diamond Club, a role which also required her to work as the elevator operator.

“I realized when I was operating the elevator, that that was an opportunity,’’ Steward said. “Every time someone came in the elevator, whether it was Mr. (Fred) Wilpon, one of the owners, I would let people know that I was interested in working in sports as a career.’’

Jay Horwitz, the team’s media relations director, hired Steward as an intern, but she still kept her gig on the elevator, which led to another life-altering opportunity. In the course of a conversation with one of Major League Baseball’s attorneys, she learned about MLB’s executive development program, and landed an internship there. She also became very friendly with Gorman, who was then a Mets executive but would later become an ally after Red Sox CEO John Harrington and general counsel John Donovan contacted MLB to see if Steward could complete her internship in Boston, then added her to the team’s legal team in July, 1988.

Two years later, Gorman came calling, creating the position of assistant GM and appointing Steward. It made headlines across the country, and attracted the attention of a particularly distinguished observer.

“My husband would have had so much respect for Elaine,’’ Rachel Robinson, widow of the Hall of Famer who broke baseball’s color line in 1947, told the New York Daily News. “She has made her way with grace, dignity and great strength.’’

Steward had long regarded Rachel Robinson as a mentor, and had turned to her for advice when the chance to go to the Red Sox first surfaced. She admitted to a few apprehensions about relocating to Boston, a city to which she had never been.

“Sometimes we’d hear stories that maybe the city wasn’t the most welcoming to African-Americans,’’ Steward said. “I talked to people. I talked to Rachel Robinson about that issue. I remember her encouraging me to give it a try.’’

Rachel Robinson did so even though her husband had been accorded a sham tryout by the Red Sox in 1945.

“I think it’s a testament to what type of person she is,’’ Steward said. “She felt I would be offered an incredible opportunity by the Red Sox, and she thought it was in my best interests to pursue it.’’

Steward soon waded into the thicket of MLB regulations, contract rules and player negotiations. The work was nonstop. There was one player agent, she recalled, who was less than receptive to her presence.

“I introduced myself and said, ‘I'm going to be negotiating this contract on behalf of the Red Sox. I've been promoted to assistant general manager, blah blah blah. And I recall that the agent told me, ‘Hold on,’ and I guess he must have put the telephone receiver down. And I heard a conversation, something about, ‘Who's this person, who’s this girl, this black girl.’

“I remember thinking, ‘OK, what am I going to do?’ So, the person picks up the phone again. And I remember saying, ‘I want you to know that I heard everything that you said.’’’

The agent couldn’t get off the phone fast enough, promising to call back. But for the most part, because of her competence and quiet professionalism, Steward said she rarely encountered pushback, even as she was involved in negotiations with some of the team’s biggest stars, including Roger Clemens and Mo Vaughn.

She laughs as she described one meeting with Vaughn’s agent, Tom Reich, an excitable sort with a paint-peeling collection of adjectives. They were meeting in the lobby of New York’s Grand Hyatt Hotel when she presented a contract proposal for the slugging Vaughn that Reich deemed lacking. As his agitation grew, so did his decibel level.

“The funny thing was, my brother Derek worked security at the hotel,’’ Steward said. “In the back of my mind, I'm thinking, if my brother walks by and sees this man upset and yelling at me, it's going to be quite a scene. Luckily, he didn't come by.’’

Duquette, mindful that Steward had no background in player evaluation, an essential component for anyone aspiring to become a general manager, encouraged her to attend scout school. But it would have required being away from home for several weeks, and with young daughters, Steward passed.

In retrospect, there is a slight tinge of regret. “I enjoyed the job I had,’’ she said, “and I look forward to the day another woman is able to take that next step.’’

Steward has devoted considerable time to mentoring young men and women. And as she follows with keen interest the current national conversation on Black Lives Matter, she remains hopeful that baseball will aspire to greater diversity.

“I feel like this is a time where people are listening,’’ she said. “I also think that we see so many videos of things happening, it’s hard to deny when the evidence is right in your face. I’m hoping this is something that’s going to stick.’’

She noticed when all 30 of MLB’s general managers held signs that said Black Lives Matter on the night of the amateur draft.

“It is meaningful to see that symbolism,’’ she said, “but what ultimately will be more meaningful is when things progress. It’s wonderful to see people recognizing with words, but actions are really the things that are going to determine if we get there.’’