TORONTO — John Chayka has been accused of a few things since he stepped on the scene as Toronto Maple Leafs general manager.
Lazy ain’t one of them.
If you thought the executive was getting a head start on off-season business — a new head coach, a series of trades, a big-fish signing, one small extension, and 10 draft picks, including the first-overall whopper — so he could kick back on a dock and enjoy Canada Day, you were sorely mistaken.
Chayka rolled up his sleeves Wednesday and grinded out two trades (godspeed, Nick Robertson and Dennis Hildeby) and five signings before your dad even got around to igniting the ol’ Weber. Not to mention all the phone calls involving a potential Zach Werenski blockbuster and a potential Morgan Rielly trade, two complicated moves that remain very much in play. (Werenski and Blue Jackets GM Don Waddell both released statements proclaiming a renewed commitment, but do not consider the file closed.)
The biggest deal is future Hall of Fame goaltender Sergei Bobrovsky at three years and $21 million, as Toronto reunites 2024’s Stanley Cup–winning tandem north of the border and guards against Anthony Stolarz’s history of injury.
“The résumé speaks for itself. Possibly ends up being the best in that position of all time,” Chayka explained of his big swing. “To be able to secure a player like that for this team that’s looking to break through, we feel like it was the right player at the right time.
“He’s looking to win. I think it says a lot about the organization, says a lot about the ownership, and a lot about the player leadership. He really believes in these guys, which is great.”
The Florida Panthers refused to meet Bobrovsky’s demands on money and term, pivoting Tuesday to the younger and cheaper Jacob Markstrom ($6 million AAV).
Surely, Goalie Bob’s numerous connections to the Leafs — ex-Panthers Stolarz, Steven Lorentz, and Oliver Ekman-Larsson, plus chief goaltending scout Curtis McElhinney — will aid in the transition. And after three consecutive trips to the Cup Final, a long summer of rest and training should serve the veteran well.
His work habits, dedication, and championship pedigree, Chayka hopes, will rub off.
“If we're going to a Game 7,” Chayka wondered, “is there another goalie in the world that we’d want in net for us?
“No. We’d prefer to have Sergei Bobrovsky.”
But there is risk here, to be sure.
Bobrovsky’s numbers fell off a cliff as the Panthers missed the playoffs; his .877 save percentage and minus-23 goals saved above expected were both career lows.
Chayka is banking on Bobrovsky’s remarkable durability (nine seasons of 50-plus starts) and playoff pedigree to be balanced off by a Stolarz bounce-back. Load management for both veterans will be key.
Should injury strike the crease, the organization can lean on prospect Artur Akhtyamov, who is hot off Calder Cup and AHL playoff MVP victories and is still on a two-way contract in 2026-27.
But not towering prospect Dennis Hildeby, who became expendable with Akhtyamov’s emergence and the Bobrovsky deal.
After breaking out with a Leafs-best .914 save percentage in 20 appearances in the show last season, Hildeby got packaged with a third-round pick (2028) and fourth-round pick (2028) and sent to Tampa Bay for 31-year-old forward Nick Paul ($3.15 million AAV through 2028-29), a two-time 22-goal man coming off a down year.
Paul is a Mississauga, Ont., native who routinely saved some of his best road performances for Scotiabank Arena. He is also one of four new Chayka signings capable of playing centre — a position of great need when everyone went to sleep last night.
“Certainly, through the spine of the team now, we feel a lot better about our centre position through the defence,” Chayka said. “We pursued everything. And Nick was a guy that, candidly, we weren’t sure was available. I think it was a good hockey trade.”
Versatile middle-sixer Jack Roslovic (two years at $4 million per), and bottom-six centres Colton Sissons (two years at $4.25 million) and Teddy Blueger (two years at $2.5 million) were all scooped off the open market.
Ditto depth wingers Zack MacEwen (two years at $875,000) and Brandon Duhaime (three years at $2.6 million).
All these depth forwards have been brought in to ramp the group’s speed and eat up some defensive-zone starts and penalty-kill minutes that, theoretically, will free up the Matthews and John Tavares lines to spend more time in the O-zone.
Outside of his splurge on power-play quarterback Darren Raddysh, Chayka has been careful not to commit term to any of his new recruits.
He did not overpay for depth, letting more enticing middle-six options like Scott Laughton, Mason Marchment, and Boone Jenner sign for more money and longer term elsewhere.
Make no mistake: Toronto’s plan is to aggressively build the most competitive and balanced hockey team for the next two seasons.
To make it faster and more mobile on the back end. Deeper up front.
Two seasons just so happens to be the commitment length laid out in captain Auston Matthews’ current contract. Not to mention that of Werenski and — dare we say — Connor McDavid, with their clubs.
As of now, Toronto’s cap picture clears up in the summer of 2028, which is shaping up to be a whopper.
In the near term, however, workaholic Chayka has marked his fingerprints all over the roster, the bench, and the front office.
How significantly different the Maple Leafs feel on July 1 from May 4, the day Chayka was hired, is impressive.
“Certainly, a player of Sergei Bobrovsky’s calibre sends a message that we’re serious about moving this team ahead,” Chayka said. “Everyone from him to the depth signings that bring us a lot of different elements and allowing our players to be put in different positions where they can have their talents come out in the best way possible, it’s a full picture.
“If you look at the full picture, we’re a much more dynamic team today than we were 24 hours ago.”
Whether this group is shaping up to be a legitimate threat in the hotly contested Atlantic Division is unknown. But at the very least, training camp will feel fresh and interesting and bubbling with hope.
Fox’s Fast Five
• Toronto’s Nick Robertson saga is finally over. The steadily improving winger was shipped off for a fourth-round pick to Pittsburgh, where he reunites with Kyle Dubas, the executive who drafted him in 2019’s second round. And unites with his boyhood idol, Sidney Crosby.
A wise bet here for Dubas, who also bought low last season on Columbus winger Yegor Chinakhov, once suggested in a change-of-scenery swap for Robertson.
Chinakov erupted for 18 goals and 36 points in 43 games for the Penguins. Dubas is hoping for a similar breakout.
Does acquiring 24-year-old Nick — coming off career highs in goals (16), assists (16), even-strength points (28), and games played (78) — entice brother Jason in Dallas to join the Pens as well?
As for Toronto, Robertson now represents poor asset management and an underwhelming return after seven years of development.
• The market dictates.
Despite his wishes to re-sign in Toronto, pending RFA Matias Maccelli was not retained at his steep $4.1 million qualifying price. That retention price killed the playmaker’s value in trade talks.
As an unrestricted free agent, Maccelli accepted a one-year, $2.25-million, prove-it deal with the New York Islanders. Much more reasonable.
• Nick Kypreos dropped an interesting note on Oilers coach and Mike Babcock disciple D.J. Smith becoming the first NHL assistant to crack $1 million in salary.
Toronto’s Jim Hiller wanted Smith on his staff, too. Bit of a bidding war.
“D.J. and I spent a lot of time together,” Hiller smiled last week. “We talked about it a little bit, but there's always different things that come into play. But him and I will remain good buddies.”
Kypreos wonders if Paul Coffey could make the switch to Toronto with defensive coach Mike Van Ryn not expected on Hiller’s bench.
• Some back-burner business in Toronto.
Restricted free agents Emil Andrae, Jacob Quillan, Ryan Tverberg, and William Villeneuve all need contracts this summer. With all the new veteran additions, it’ll be difficult for Marlies to crack the lineup.
• We don’t believe Chayka is done done. But were the season to start today, Toronto’s lineup might look something like this:
McKenna – Matthews – Roslovic
Knies – Tavares – Nylander
Paul – Sissons – Cowan
Joshua – Blueger – Duhaime
Rielly – Raddysh
McCabe – Tanev
Ekman-Larsson – Stecher
Bobrovsky
Stolarz
TOR