Before getting to that point, Steward learned about the Jackie Robinson Foundation program that was offering a sports management scholarship at St. John's University. Steward landed that scholarship and earned a law degree, and the rest, as they say, is history.
Following an internship with the Commissioner's Office under Peter Ueberroth, Steward got a job with the Red Sox in 1988.
In 1990, the Red Sox promoted Steward to assistant general manager under Lou Gorman. It marked the first time a black woman earned a position that high in a front office in the Majors.
"Lou Gorman was looking for someone to assist him with a lot of the administrative parts of his job," said Steward. "They asked me if that sounded like it would be something that would be of interest to me. Obviously it was. It was an incredible opportunity. They interviewed a number of folks, but I ended up being selected to fulfill that position and work with Lou. It was really like a dream come true."
For a few years, Steward assisted Gorman -- and briefly Dan Duquette -- on player contracts. She currently handles legal matters for the Red Sox, working as vice president/club counsel.
"And coming here, there were so many mentors -- Lou Gorman was wonderful, John Harrington, Mrs. Yawkey was great to me," Steward said. "These are people that made a decision to give me an opportunity and to give me the tools to do it and they had faith in me and I'm forever grateful for that."
Did Steward know she was paving the way for other minorities and women to rise through the ranks with baseball franchises?
"I was obviously aware of it, but I think the way my parents brought me up was that whatever I was interested in, work hard towards it, and I always felt like I should go for what I was interested in," said Steward. "If someone else had a problem with it, that's their problem. I just put my best foot forward and do the best that I can, work hard and hopefully things work out."
That motto has worked for Steward for nearly 30 years now with the Red Sox. She appreciates her place in baseball history, but she has never been a self-promoter.
"I was proud of that. There was, at that time, some level of interest in the story," Steward said. "I tend to be a bit of an introvert, so that may not have always been that comfortable for me. But I did realize that it was important to other people that story be out there so other people could be inspired as I've been inspired by people before me."
Mentorship is an ongoing thing for Steward, and it stretches from strangers to her own children.
"I do get a lot of calls from folks, and yes, I do enjoy mentoring younger folks," Steward said. "I have three daughters now. One of them has recently entered into the business world. The other two will be doing that very shortly. I do understand the importance of mentoring young folks. It really feels good when you're able to help someone along the way."
As for Black History Month, Steward thinks it is crucial.
"I think schools don't really focus on black history enough," said Steward. "I know when I was going through school, it might be a couple of sentences here and there in a history book. I think it's very important that we understand what contributions have been made by black people. Anyone who contributes to the betterment of our lives should be recognized. I believe some of this has been trivialized or ignored, so I do feel that Black History Month is very important, because it is a time to highlight some of these contributions that have happened."