Jillian Dempsey and Kali Flanagan have spent their entire lives in Boston. Now the local legends will be heading north of the border to play with PWHL Montreal and Toronto respectively.

When Jillian Dempsey signed in Montreal, and Kali Flanagan landed in Toronto, the city of Boston shivered. It was almost as if someone were playing a wicked trick on the hockey city.

Jillian Dempsey has played hockey in Boston since the day she stepped on the ice. From The Rivers School in high school, she went on the captain Harvard University, playing four seasons for the school.

When she graduated, Dempsey was named the CWHL Rookie of the Year with the Boston Blades, and the next season won a Clarkson Cup with the team. From there, she joined the Boston Pride, a team she'd spend eight years, the entire existence of the NWHL and PHF playing with, including winning three Isobel Cups, a league MVP honor, and captaining the team for six seasons.

Perhaps that's why looking at Dempsey's resume and seeing "Montreal" next to her name for this season, felt very strange for Boston fans. The reaction online was strong, as one post noted, "Boston isn’t Boston without Jillian Dempsey in it."

Dempsey herself acknowledged the mixed feelings of leaving the city in an Instagram post.

"It has been one of the greatest joys of my life playing the past 10 seasons for Boston, my home. A dream come true. I am absolutely devastated that the Boston Pride no longer exists. It’s still so hard to process. I am beyond grateful for the incredible moments and memories. And I always appreciate the unwavering support from our dedicated and passionate fans."

Dempsey isn't alone in this either. 

Kali Flanagan is another Boston product who has spent her entire life in New England. The defender played her NCAA hockey for Boston College before staying in New England with the PWHPA, and the past two seasons, playing alongside Dempsey with the Boston Pride, winning an Isobel Cup title, and last season being named the PHF's Defender of the Year.

For the Massachusetts born and raised duo, it's a new phase to their professional hockey journeys. They'll certainly receive a warm welcome when they return to their home state for the first time this winter as members of Montreal and Toronto.