Jillian Dempsey put teaching on hold to continue playing hockey. Then her world turned upside-down.

Jillian Dempsey won three Isobel Cups as a member of the Boston Pride.Jim Davis/Globe Staff

This spring, Jillian Dempsey took one of the biggest risks of her life.

The Boston Pride’s six-year captain and one of the Premier Hockey Federation’s most well-known players decided this was the year she would pursue professional hockey full-time. Instead of the evening practices the Pride had previously held, the team planned on moving to daytime sessions that would interrupt their players’ abilities to hold down other jobs. League salaries were increasing, so more availability was expected.

That meant giving up the other job Dempsey loved: as an elementary school teacher in her hometown of Winthrop. It was a job she proudly held, juggling it with her pro hockey career. If there was a Pride media availability before an evening practice, she typically took it from her classroom, an array of brightly colored books behind her.

“I had to decide to keep playing or teach at school,” said Dempsey, a 2013 Harvard graduate. “Obviously I wanted to continue playing as long as I can, so that was a tough decision to make.”

Dempsey made the call to take a leave of absence from teaching and devote herself to the Pride full-time, only to have her world changed within a week of packing up her classroom materials.

Now Dempsey is packing again — to move to Montreal.

Dempsey signed a one-year deal with the Montreal franchise of the brand-new Professional Women’s Hockey League Thursday. She is one of many former PHF players with changed plans after the league was acquired by Billie Jean King Enterprises and the Mark Walter Group at the end of June.

The acquisition of the league voided all PHF contracts, including Dempsey’s two-year deal set to expire at the end of the 2023-24 season. It also left many players and most staff out of work. The move tasted sour to some, as the PWHL also uses much of the leadership and key player representatives of the former Professional Women’s Hockey Players Association, an organization founded in 2019 by US and Canadian national team players.

PWHPA founders held showcase events throughout the US and Canada, lobbying for a more organized league with higher salaries and more professional venues. In response, the PHF made multiple moves since 2020: new leadership, improved facilities, better player benefits, and higher salaries.

Though the new PWHL promises to increase the exposure of women’s hockey and provide what it deems a true professional experience, it has caused chaos for former PHF players.

Even though Dempsey scored 161 points during her 158 games with the Pride (not to mention 48 points in 52 games with their predecessors, the CWHL’s Boston Blades), she was not a pre-draft signing by the Boston team or the other five PWHL franchises. Not one PHF player was.

The PWHL was announced Aug. 29, and players had until Sept. 3 to declare for its inaugural draft. Very quickly after that cutoff, on Sept. 6, each PWHL team announced three initial free agent signings from that pool. All of those initial signings had ties to the PWHPA. Everyone else, including the PHF players who declared, were left to be drafted.

The contracts PHF players had signed were not honored or taken into account in the initial free agency process because they were considered void as of July 10.

“Of course, I was hopeful at first to have an opportunity to be one of those early free agent signings,” said Dempsey. “That would’ve been ideal. Or to have there be a greater free agency period [before the draft], especially for players who are veterans or who have played multiple years of pro hockey.”

At the Sept. 18 PWHL Draft in Toronto, the first former PHF player was not selected until the fourth round. Dempsey’s former teammate Loren Gabel, the league’s top scorer and 2023 MVP, was selected three picks later by PWHL Boston.

Dempsey was the 66th overall pick, and she was surprised to be selected by Montreal.

“I had no inkling of whether I was going to be drafted, and if I was, where I was gonna be drafted,” said Dempsey. “I was hoping to continue my career in Boston the way that I had envisioned.

“After playing 10 years of professional hockey in Boston, it was a bizarre situation to all of a sudden be put into a draft and really have no clue, no say, and no choice of what’s going to come of that.”

The PWHL did offer players a waiver to apply to play for a certain team if they had a family or another compelling reason. Dempsey did not use the process because she believed it was for players with children or with similar caretaking situations. She said many of the players she knows who applied for the waiver did not receive it.

Staying true to her springtime decision to pursue pro hockey full-time, Dempsey is up for the challenge that a new league and city will bring. She has been told to be in Montreal for training camp by Nov. 15, but some aspects of the league are still being ironed out, including venues, schedule, and playoff structure.

After her three championships with the Pride, the playoff structure is something Dempsey is curious about.

“I’m not even sure what we’re playing for,” said Dempsey. “In the past we had the Isobel Cup, so it was clear that that was the endgame. The ultimate goal was to win the Cup. It’s still a little hard to formulate some of those goals [for the season] right now with the little knowledge that it feels like we have.”

Despite the tumultuousness of the PHF’s acquisition, Dempsey is eager for another chance to play pro hockey. But one thing gnaws at her: She never got a chance to say goodbye to her Pride teammates and the enthusiastic fan base that had been selling out Brighton’s Warrior Ice Arena most weekends last season.

She tears up when she talks about the abrupt ending to her time with the Pride.

“One of the incredible joys of my life was to represent my city,” said Dempsey. “I appreciate all those experiences and everybody who’s been there for that part of the journey. I don’t know what’s going to come of anything, but before my career is up, it would be great to be able to represent them again.”