Stu Cowan: Jillian Dempsey has put teaching career on hold for PWHL

A legend in women’s hockey in Boston who also taught Grade 5 for nine years, she had to make adjustments after getting drafted by Montreal.

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Jillian Dempsey has two big passions in life: hockey and teaching.

The Boston native had to temporarily give up the second one — teaching Grade 5 at Cummings Elementary School in Winthrop, Mass. — after being selected by Montreal in the 11th round (66th overall) of the first-ever PWHL Draft last September for the six-team league’s inaugural season.

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“Very unexpected,” Dempsey, who is from the Boston suburb of Winthrop, said after a practice last week about moving to Montreal. “It’s been a year unlike any other for me. Lots of adjustments. Trying to adapt to a new environment, a new position in hockey (as a fourth-liner), a new life, really.

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“I’ve been teaching and playing for the past nine years,” the 33-year-old centre added. “I’m very passionate about my teaching job, too, so I’ve really missed that this year. Just a lot of adjustments. I’ve come a long way and here we are in the home stretch. My goal for finishing out the year is for us to be champions. That’s the ultimate.”

Montreal’s season could come to an end Tuesday in Game 3 of its semifinal series against Boston at the Tsongas Center in Lowell, Mass. (7 p.m., TSN3, RDS2, YouTube). Boston won the first two games of the best-of-five series by identical 2-1 scores, with both games going to overtime. Taylor Wenczkowski scored the winner for Boston in Game 2 at 11:44 of triple-overtime Saturday night in front of 10,172 fans at Laval’s Place Bell.

Dempsey is a women’s hockey legend in Boston and her story is a common one for players in the PWHL as they try to juggle their lives on and off the ice. The women got to this point by playing for the love of the game — without fame and fortune like NHL players — and are finally able to have a real professional league of their own. The minimum salary in the PWHL is $35,000 and six players must be paid a minimum of $80,000.

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After graduating from Harvard University, where she was team captain in her senior season, Dempsey played two seasons for the Boston Blades in the old CWHL, followed by eight seasons with the Boston Pride — where she was also captain — in the NWHL and PHF before the PWHL was formed. She finished as the all-time leading scorer in the PHF with 146 points in 142 games. In 24 regular-season games with Montreal, Dempsey had 1-3-4 totals in a reduced role from what she was used to previously.

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“More limited, but just trying to make an impact when I am out there and try and bring energy and be relentless on forechecks and be difficult to play against,” she said.

As someone who grew up as a big Bruins fan, Dempsey said it was “very bizarre” at first being on the other side of the Boston-Montreal rivalry.

“But this is my team this year,” she added. “I want us to come out on top.”

There will be a lot of fans cheering for Dempsey Tuesday night, including students and colleagues from Cummings Elementary, where she taught for nine years. Andrea O’Leary, the principal, was among those from the school cheering for Dempsey when Montreal played its first game in Boston during the regular season, winning 2-1 in OT.

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“We were sitting in the Boston section and people were not happy,” O’Leary recalled in a phone interview Monday. “We all wore our Dempsey gear as well. We also had signs that said, ‘Bring her back to Boston.’”

O’Leary said the students at the school really miss Dempsey as a teacher.

“I miss her, too, and I would love her to be back,” O’Leary said. “But I understand that at the age she’s at there’s only so many years left to play. So I think that’s a decision that she has to make. We miss her terribly.”

What makes Dempsey a good teacher?

“She has this unbelievable ability to be organized, to be structured and to focus on the task at hand,” O’Leary said. “For example, she was a professional athlete and taught fifth grade for all of those nine years. Never calling in sick, never missing days. Always being overly prepared for her classroom as well as always prioritizing her practices and maintaining her health for hockey. The ability that she had to do both so well is a very, very special talent.”

Dempsey hopes to eventually go back to teaching at Cummings Elementary and O’Leary said the door is open for her. The principal would also like to see Dempsey play for the Boston PWHL team.

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“She definitely was one of the major faces of the Boston Pride and she was the captain and she worked so hard,” O’Leary said. “When they won the Isobel Cup (as PHF champions) multiple years, she would bring it to school. She would stand outside after school and take pictures with every student, with every family. She connected with children that were older as well as younger.

“She really was the face of following your dreams and doing what you love,” the principal added. “For her to have two strong passions is amazing.”

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