Sergei Bobrovsky twice broke the hearts of his new team.
The Maple Leafs are hoping the veteran goaltender will now help get their tortured franchise back on track.
Toronto signed the two-time Stanley Cup winner to a three-year contract worth a reported US$21 million as NHL free agency opened Wednesday.
Bobrovsky, who eliminated the Maple Leafs from the 2023 and 2025 playoffs as a member of the Panthers, hit the open market at 12 p.m. ET and will partner with Anthony Stolarz after hoisting hockey's holy grail together with Florida two years ago.
Owners of the league's longest title drought, Toronto missed the post-season for the first time in a decade to cap a miserable 2025-26, but beat the draft lottery odds and selected winger Gavin McKenna with the first pick before adding Bobrovsky — along with at least three depth forwards in Jack Roslovic, Colton Sissons and Teddy Blueger — via free agency on Canada Day.
Maple Leafs general manager John Chayka, who was hired in May, continued his roster renovation by dealing Dennis Hildeby from a crowded crease along with third- and fourth-round picks to the Tampa Bay Lightning for centre Nick Paul.
A few hours before the 37-year-old Bobrovsky pivoted to a new chapter in Toronto alongside Auston Matthews and William Nylander, a fellow Russian committed long-term to another Original Six franchise.
The Canadiens inked 20-year-old forward Ivan Demidov to a $73.2-million contract extension through 2034-35 that kicks in after next season as Montreal locked up another key piece of its peach-fuzzed core.
"I'm happy to be here," Demidov told reporters in Brossard, Que. "I can't wait to play more games for this jersey."
The Edmonton Oilers freed up a boatload of money by trading Darnell Nurse to the San Jose Shark for fellow blueliners Shakir Mukhamadullin and Zack Sharp in a swap that didn't include any dollar retention.
Nurse counts $9.25 million against the salary cap through 2029-30, and GM Stan Bowman now has more flexibility to build around Connor McDavid and Leon Draisaitl.
The Sharks also got bigger in free agency by adding blueliner Jacob Trouba (four years, $33 million) and forward Mason Marchment (five years, $33.75 million).
The Vegas Golden Knights re-signed unrestricted free agent defenceman Rasmus Andersson to a reported seven-year, $59.5-million contract.
The Winnipeg Jets inked goaltender Stuart Skinner to a two-year, $7.5-million pact with the future of Connor Hellebuyck up in the air.
The Chicago Blackhawks signed defenceman Bowen Byram to a contract worth $75 million over six years that starts in 2027-28 after a recent trade with the Buffalo Sabres.
The New Jersey Devils agreed to a five-year, $58.5-million extension with captain Nico Hischier beginning in 2027-28.
Apart from adding Bobrovsky — a two-time Vezina Trophy winner as the league's top netminder — Toronto also signed Sissons (two years for a reported $8.5 million), Roslovic (reportedly two years, $8 million) and Blueger (two years for a reported $5 million) after shipping winger Nick Robertson to the Pittsburgh Penguins for a fourth-round pick.
The Washington Capitals signed UFA centre Boone Jenner to a four-year, $23-million contract, and the Panthers inked forward Eetu Luostarinen to an eight-year extension worth a reported $40 million beginning in 2027-28.
The Vancouver Canucks brought defenceman Luke Schenn back on a one-year, $2.25-million contract, while Ottawa Senators re-signed pending UFA forward Nick Cousins to a two-year, $3.175-million deal.
Elsewhere around the league, the Dallas Stars traded restricted free agent Mavrik Bourque and defenceman Ilya Lyubushkin to the Nashville Predators for a 2027 second-round pick and a 2028 third-rounder.
The Philadelphia Flyers re-upped goaltender Dan Vladar to a five-year, $27.5-million extension that begins in 2027-28. The club also locked up forward Tyson Foerster on an eight-year, $56.8-million contract that also kicks in after the upcoming season.
The Lightning signed winger Ilya Mikheyev to a four-year, $15.5-million deal and the Seattle Kraken kept RFA forward Mackie Samoskevich on a three-year, $11.55-million agreement.
The St. Louis Blues came to terms on a one-year, $850,000 contract with Dillon Dube after he played for the club's American Hockey League affiliate in 2025-26. The centre was among five members of Canada's 2018 world junior team acquitted in a high-profile sexual assault trial last summer.
This report by ºÃÉ«tvwas first published July 1, 2026.
