It is hard for outsiders to truly understand what Jillian Dempsey meant to Boston’s women’s hockey landscape. She was born and grew up in the greater Boston area. She played four years at Harvard and was named captain for her senior year. After university, she went to the CWHL with the Boston Blades for two seasons before joining the PHF (then-NWHL) with the Boston Pride, where she played for all eight seasons of the league’s existence. The last six of those seasons, she was the team’s captain.
She has been at the centre of the professional Boston women’s hockey scene for a decade. During Monday’s PWHL Draft, it was the first time where she didn’t have a say in where she was going to play.
“It was definitely nerve wracking,” she said. “Up to this point, I’ve always had control of where I’ve played and I’ve been fortunate that that there’s been a team in my in my home this whole time, between the Canadian Women’s Hockey League, Boston was the only American team option. And then obviously, in the PHF, having a Boston team, so it was definitely a nerve wracking experience just waiting to find out my destiny for the season and where I would end up. And it was a feeling that we’re not used to.”
Dempsey, for the first time this season, has been working with Hecate Sports Group and Eleni Demestihas as her agent. She says that while there was communication with teams prior to the draft and since the free agency period opened, she had no idea of what to expect going into the Draft. She didn’t even know a range of when to expect her name to be called.
She followed the draft online. She wasn’t sure if her name would be called at all, but when she finally did see her name pop up, it was not only not next to Boston. It was next to probably their biggest historical hockey rival: Montreal. Considering as a nine-year-old, Dempsey literally named the Bruins mascot in a contest, it feels a little weird but she didn’t let it show.
“I’m honoured to be selected by Montreal, they’re very similar to Boston with a passionate fan base,” she said. “They love their hockey and it’s just a great city that really, really cares about hockey. I’m grateful that Montreal saw something in me and valued me as a player that they wanted to choose me in the draft.”
Dempsey said that after she knew she wasn’t going to be signed before the draft, the next goal was to be drafted and not be one of the many talented players needing to fight for a training camp invite in free agency.
A Summer of uncertainty
If getting drafted by Montreal was the ‘We’re not in Kansas anymore’ moment, the start of the tornado came in June when it was announced that the PHF would no longer exist as the league owners sold some league assets to the Mark Walter Group and make the PWHL the only league. Players like Dempsey, who had contracts for this upcoming season would have to see if they got a spot in the PWHL.
“It’s been a whirlwind of a path, obviously, we had plans for the upcoming year squared away and were looking forward to it and then for many of us, having the rug swept out from underneath us…” she said. “Throughout the summer, there was just so much uncertainty, and not really knowing what to expect and there was just nothing that felt solid and known. And that was definitely hard. Not knowing what the season was going to look like. And definitely disappointing and sad to lose the Boston Pride and to be done with the PHF as someone who had been there for all eight seasons, and felt like made a lot of growth and positive strides over that time, and really built fan bases in community. There were a lot of mixed emotions with everything that happened at the end of June. And it was great to finally have some answers and have a timeline and logistics about what to expect with the new league.”
Even though she followed the Draft online, she felt a lot of the professionalism in Monday’s Draft that so many players and analysts have pointed out.
A balancing act
When Dempsey started playing professionally in the CWHL, there were no salaries, and players were given bonuses for winning the regular season championship or Clarkson Cup. Because of that, she chose to also pursue another passion as a teacher. Many women’s hockey players after university – especially those not on national teams – have needed second jobs. Dempsey’s path was perhaps one of the most publicized, even down to teaching her class via Zoom from the PHF’s attempted bubble in Lake Placid.
Even before the PHF had ceased operations, Dempsey had planned to take the year off of teaching. The Pride were slated to, for the first time, practice during the day. The 32-year-old wasn’t ready to stop playing hockey, so she set aside teaching.
“I absolutely love being a teacher, it’s my other passion,” she said. “I have hockey, and I have teaching. And those are the two things that I’m really passionate about and I love doing and they’ve gone hand in hand for so many years now, actually, nine. I played pro hockey for 10 years and been teaching and playing for nine. And so this year was the first year where I actually was taking a leave from teaching. That was a tough, tough decision in the sense that these were two things I balanced so well for so many years and I love both.”
Despite splitting her time between her two jobs, she was able to continue playing at a high level. She finished as the PHF’s all-time leading scorer, and last season was third in league scoring. In 142 career PHF games, she had 146 points.
She will now have to negotiate a new contract with Montreal for the PWHL season, and there are obviously a lot of factors to consider when it comes to being financially comfortable with one income, which would have been the case with her PHF contract. Even with this latest hurdle of uncertainty, she still looks back fondly at her path.
“Since my professional career has started, the game has come incredibly far,” she said. “When I first graduated college, and I was in the CWHL, we were busing to Brampton and to Toronto. In the second year, we were able to fly, there was a huge improvement, and everybody was very excited. If you came in first place, I think it was you win $500. And then if you won it all, you get another $500. And so it’s just remarkable, the gains that we’ve been able to make in the past decade, since when I graduated college, and the players coming out of college into this women’s hockey landscape right now. So that’s something I reflect on often, just the incredible growth. I loved my time in the CWHL playing for the Blades, even though some of the standards were lower than what we have now in terms the resources and how players were treated. I was grateful to get to play competitive hockey after college, because that was something that when I was growing up, there wasn’t really an option after college.”
She hopes that eventually there will be even greater gains from the current PWHL CBA where six players will get at least $80,000 US per season, and the league average will be $55,000. Players also get relocation and housing stipends. But she’s also looking forward to getting back on the ice and does so knowing that she has another passion waiting for her when she does hang up her skates.