EHSA News
EHSA Revives Scholarship Honoring Legendary Coach Bill Stewart

Coach Bill Stewart Jr. doing what he did best.
In any given year, there are some 37,000 high school athletic coaches in the United States. The best ones know that the job is not just about wins and losses. It’s also about shaping young hearts and minds, inspiring students and creating a positive legacy. And perhaps no high school coach in recent decades has exemplified the position as well as ‘Coach Bill’ Stewart, Jr., EHS ’37, who during his 50-year coaching career — including 37 years as football, baseball and hockey coach at English High School mentored more than 4,000 students.
English High Alumni along with family, friends, former colleagues and athletes – as well as members of the community at large – are delighted that the Coach Bill Stewart Jr. Scholarship has been revived by The English High School Association. The scholarship was originally established on December 8, 1987, two days after Coach Bill passed, and is now awarded to the English High graduating senior athlete boy and girl who best exemplify academic achievement, competitiveness, spirit and good sportsmanship. The 2024 recipients are basketball player Elijah Smith and softball player Rose Monestime.

William Stewart III, son of Coach Bill Stewart Jr., at the English High 200th Anniversary Gala in 2022
The impetus for reviving the award came from Coach Bill’s son, William Stewart III, who heard from so many who wanted to keep his dad’s memory alive. He enlisted the help of one of Coach Stewart’s former players and President of EHSA, Mike Thomas ’67. Although initially stone-walled, Billy’s insistence and EHSA’s perseverance paid off. The Coach Bill Stewart Jr. Scholarship funds were discovered (after 11 years of being unawarded) in the Boston Schools’ Trust where they were misfiled under the wrong spelling of the ‘Stewart’ name. During Bill III’s career as a teacher and probation officer, he also mentored thousands of young people.

Coach Bill Stewart Jr. and young William Stewart III (number 84) on the sidelines of the 1957 English v. Latin game. English went on to win the Thanksgiving Day game 26-20.
“I was my father’s shadow, following him into rinks, stadiums, baseball fields, even into prison baseball games,” Bill III remembers. “I listened when he was a featured speaker at banquets and at kitchen tables when he visited homes of players. I remember countless phone calls from people who needed his advice to help solve problems of all kinds. I remember kids, all shapes, sizes and colors, who stopped by our house in Mattapan or Jamaica Plain to grab a minute with ‘Coach.’ No matter what time of day, we would have visitors and my mom would feed them.”
Bill says, “One of my dad’s favorite lines to his players was, ‘You want to be a little bit better when you go to bed than when you get up. So when you look yourself in the mirror, you can say to those eyes looking back at you, ‘You had a good day.’ I can’t tell you how many times in my four years of teaching and 40 years of probation work I used those thoughts in my lectures to law enforcement groups in the 38 states and three countries I travelled to, teaching and working with youths involved in the court systems.”
On accepting the Coach Bill Stewart Jr. Scholarship funds, Mike Thomas, who played football and baseball under Coach Bill in 1964-7, told Bill III, “I know you made your dad proud. You are the perfect Stewart to be in the English High family. I applaud you because it’s people like you that make our job easier.” Coach Bill’s constant reminder was to ‘Keep your head up!’ All he would ask, win or lose, ‘Did you try’? If you could say you did, then you didn’t quit on something or someone.
Read more about Coach Bill Stewart Jr.

Isabella Bittorie ’24
Coach Bill had such a profound lifelong influence on Richard Long ’52, a kid from South Boston, that 72 years after his graduation, that ‘kid’ established another scholarship in Coach Bill’s memory for a college-bound student-athlete. Long, who played football and ran track at English High, says, “I’m happy to make this gift, a sort of giving back to English High, and a gesture of thanks to Coach Bill. It brings back memories. And but for Coach Bill, where would I be?”
The first Richard Long Scholarship honoring Coach Bill was awarded to Isabella Bittorie ’24, a member of the English High Volleyball and Softball teams. Isabella is planning to attend Suffolk University, majoring in Criminal Justice.
“I see now the reawakening of what the 200-plus years old spirit of English High School is about. The spirit may have flickered but it was never extinguished. I see today a renewed pride in graduating and becoming a member for life in the English High family.”
For information on establishing a Family or Memorial Scholarship to benefit English High students, contact EHSA President Michael Thomas ’67 at 857-547-1391 or mthomas@englishhighalumni.org
2024 Recipients of the Coach Bill Stewart Jr. Scholarship
Elijah Smith ’24
Basketball
Elijah Smith was one of five seniors that played a significant role in helping the boys basketball team reach their 2nd straight Elite 8 performance. He is a skilled player who works hard and has solid skills, and more importantly he is a great student athlete and strong role model for the greater English High Community.
Elijah plans to attend Bunker Hill Community College in the fall where he will play basketball.
Rose Monestime ’24
Softball
Rose has been a four year member of both the Softball and Basketball teams at The English High School. For softball, Rose was the team’s MVP for the 2023 and 2024 seasons, making pitching appearances in 36 games, and recording 100 strikeouts in the 2024 season. Rose has been a part of three state tournament teams.
Rose plans attend Bunker Hill Community College where she will play sports and work toward a career in healthcare. Ultimately, she hope to work in the field of pediatrics.