Star Athlete Takes On Fifth Grade Teaching Position

By Kate Anslinger

Winthrop school district is honored to welcome back one of its finest students and athletes, Jillian Dempsey, as a fifth grade teacher. Born and raised in Winthrop, Dempsey received her masters in Education from Boston University prior to completing Teach for America. She started her teaching career at a public school in Lawrence, where she has been teaching for the past two years. While Jillian’s educational background is exceptional, her athletic resume proves to be just as impressive. Dempsey’s drive and determination has led her to be a remarkable athlete. She has left a legacy at Winthrop High as a star hockey player and will now leave her mark as an educator. In the interview below, Dempsey shows enthusiasm for joining the Arthur T. Cummings team and shares some of her athletic and career goals.

Who is your role model?

I was so fortunate growing up to have such incredible teachers (many of whom are still teaching in Winthrop). My older sister, who is currently a Grade 6 science teacher, definitely inspired me to become a teacher.

You are a well-known athlete. Do you think the discipline you’ve learned in hockey will help you in the classroom?

My experience playing hockey has taught me invaluable lessons about discipline, perseverance, resilience, hard work, and whole-heartedly chasing my dreams. Being a competitive athlete and playing at the highest level has absolutely helped me develop skills that I use in the classroom and everyday life.

Can you share a bit about trying out for the women’s Olympic hockey team?

In June 2013 (a month after graduating college), I was selected to tryout for the 2014 Winter Olympics in Sochi. It was a humbling opportunity, and unfortunately I didn’t make the team. However, I’ve continued my intense training and spent the past three years playing professionally – 2 years in the CWHL (Canadian Women’s Hockey League), and last year in the NWHL (National Women’s Hockey League). I am working hard to earn another opportunity to tryout for the 2018 Olympics. I’ll be playing for the Boston Pride again next season in the NWHL (home games are at the new Boston Bruins practice facility, The Warrior Arena, in Brighton).

You taught in Lawrence for a couple of years. What made you decide to come back to Winthrop?

I was thrilled to see the Grade 5 opening in Winthrop. I love my hometown and am grateful for all the positive experiences I had growing up in Winthrop Schools and in Winthrop youth sports, so I am ecstatic to be part of the Cummings School team!