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The Tradition

Jillian Dempsey is living the dream, doing two things (teaching, professional hockey) she loves

Jillian Dempsey is a four-time PHF All-Star who has captained the Boston Pride for five seasons.Mary Schwalm

Like superheroes, Jillian Dempsey lives a dual life.

By day, Dempsey is a mild-mannered fifth-grade teacher in the Winthrop Public Schools. By night — or to be honest, sometimes at sunrise as well — she dons her skates as a professional hockey player who is speedy and assertive, dangerous near the net, and dogged when she plays defense.

Dempsey, the longest-tenured member of the Premier Hockey Federation’s Boston Pride, says this dual life is exactly what she wants, because it gives her the chance to change the lives of her students and advance women’s professional hockey.

“I always say that I’m living the dream because I’m doing two things that I really love,” said Dempsey. “I’m passionate about hockey and I was passionate about being a student. Now I’m passionate about being a teacher, still being part of the classroom, and learning something every day.”


The passion for hockey has earned Dempsey honors at Wednesday’s The Tradition hosted by the Sports Museum at TD Garden. In her eighth season with the Pride, and her fifth serving as team captain, she is one of the league’s most decorated players. She became the first player in PHF history to win three Isobel Cups. A four-time PHF All-Star, she also was named the league’s regular-season MVP in 2020 and postseason MVP in 2021.

Jillian Dempsey, right, is a four-time PHF All-Star.MARK STOCKWELL FOR THE GLOBE

“I looked at the names of the other recipients and those who had received the award in the past, and I was just truly humbled to be in that company and to be honored by such a prestigious award,” said Dempsey. “There’s so much legacy and history behind this event, so I was definitely thrilled to be honored.”

Dempsey’s hockey success began as a youth player in Winthrop, where she was encouraged to take the ice by her father, John, a firefighter. She played her high school hockey at Rivers, where she was an Independent School League MVP and earned the Boston Bruins’ John Carlton Award, which is given to outstanding female and male student athletes in Massachusetts high school or junior hockey. During that time, she won gold with Team USA at the 2009 under-18 world championship.


Years ago, Dempsey’s father took her to watch area women’s college teams, showing her what was possible in the sport. Dempsey especially enjoyed watching the Harvard teams led by 2021 Tradition honoree Angela Ruggiero, and set her sights on playing for the Crimson. She did just that from 2009-13, recording 76 goals and 72 assists. A captain her senior year, she was a three-time ECAC All-Star and a two-time Patty Kazmaier Award nominee.

Playing at Harvard gave Dempsey an approach to hockey that she carries with her.

“In my time there, we really took pride in having that team-first mentality and being tough to compete against,” said Dempsey. “We really tried to focus on having more heart and more hustle than the opponent.”

By the time Dempsey graduated from Harvard in 2013, there was an option to play women’s professional hockey, and so Dempsey had a new hockey goal, to play at the next level. She began her post-college hockey career in the Canadian Women’s Hockey League, playing for the Boston Blades. It was a growing league, but it could not afford to pay its players.

When the PHF (then known as the National Women’s Hockey League) began in 2015, offering to compensate players, Dempsey made the jump. There were growing pains when it came to payments, venues, and communication, and she saw several teammates leave and form a rival organization, the PWHPA.


Dempsey stuck with the PHF, and she has seen increased compensation, better structure, and league expansion during her career, especially this season. The Pride, who are 5-1 this season, have become the class of the league, not only because of their titles, but because of how they operate.

“I have been able to see so much of the growth and progress with the organization and even the league over the past eight seasons,” said Dempsey. “Being part of the Boston sports culture, we have high expectations. The goal every single season is to go out and win, period.”

Dempsey is in her fifth season as captain of the Boston Pride.Barry Chin/Globe Staff/The Boston Globe

Even as PHF compensation has increased, Dempsey still juggles hockey and teaching. She trains on her own early in the morning on the same ice she learned on, then practices with the Pride when done teaching for the day. Her students know about her dual life, and often cheer on the Pride at home games.

Dempsey hopes that her path teaches her students to be courageous in pursuit of their dreams.

“I hope my students learn to push through adversity,” said Dempsey. “You don’t find success right away. I really try to emphasize to them that things take consistent hard work. When you finally reach that success, it feels that much better knowing how much effort goes into it.”


Kat Cornetta can be reached at