There’s something different about the way new general manager John Chayka is putting his Toronto Maple Leafs team together. It’s easy enough to look at the names coming in and judge them individually. But when you step back and look at the whole offseason, another possibility starts to show up. Maybe Chayka isn’t just shopping for talent. Maybe he’s also shopping for players who know what winning hockey looks like.
We’ve seen something like it in Toronto before. In the early 1990s, the Maple Leafs brought in players from successful organizations and slowly changed the character of the team. I’m not suggesting Chayka is trying to copy Cliff Fletcher, but the similarities are hard to ignore. And then there’s Jack Roslovic, who is already getting some help from Auston Matthews as he settles into Toronto.
Maybe these things don’t amount to much. Maybe that’s part of what Chayka is looking for — not just more players, but guys who can help change the feel of the room.
Chayka May Be Looking for More Than Talent
There’s another part of this Maple Leafs offseason that I find interesting. When you look at some of the players Chayka has brought in, it seems like he is paying attention to more than what they can do on the ice. A recent report, based on a discussion on The Athletic Hockey Show, suggests that Chayka isn’t simply looking for individual talent; he is looking for players who have experienced winning environments.
That idea has some history in Toronto. In the early 1990s, Fletcher brought in players from the Calgary Flames and Edmonton Oilers, two organizations that had been at the centre of the NHL’s winning culture. Doug Gilmour, Jamie Macoun, Grant Fuhr and Glenn Anderson were among the players who joined the team through that approach. It wasn’t the only reason the Maple Leafs reached the conference final in 1993 and 1994, but it certainly helped change the character of the room.

Chayka seems to be taking a similar approach, although the teams are different. Toronto has added players with connections to recent winners and contenders, including Darren Raddysh and Nick Paul from the Tampa Bay Lightning, Sergei Bobrovsky from the Florida Panthers, Colton Sissons from the Vegas Golden Knights and Jack Roslovic from the Oilers. Former Panthers Steven Lorentz and Anthony Stolarz also bring experience into the room. These aren’t random additions. There seems to be a pattern.
That doesn’t mean winning experience is some magic ingredient. It isn’t. The Maple Leafs still have to play better hockey, stay healthy and get key players performing when the games matter most. But there is something to be said for bringing in players who have been around teams that understand what playoff hockey actually demands.
Matthews Is Already Playing Tour Guide for the Leafs’ Newest Forward
Turns out Matthews isn’t just the Maple Leafs’ captain on the ice; he’s apparently also their unofficial welcome wagon. Roslovic has been leaning on Matthews quite a bit since signing his two-year, $8 million deal with Toronto – the two have connected multiple times as Roslovic settles into a new city. Roslovic said Matthews has been showing him around, helping him figure out where to live, and getting him plugged in with the people around the organization.

(Sam Navarro-Imagn Images)
The two apparently go back a ways, and Roslovic made it clear the familiarity is a big part of why he’s excited about the move. He noted it’s been fun getting the chance to play with someone he’d already had success with, that he’s heard good things about the locker room, and has already started chatting with teammates in group messages. It’s the kind of comfort factor that doesn’t show up in a box score, but can matter a lot when a player is trying to find his footing on a new team.
Whether that friendship translates into on-ice chemistry is the real question, and Roslovic’s résumé suggests there’s real upside if it clicks. He put up 21 goals and 15 assists in 68 games with the Oilers last season, and comes in with 123 career goals and 173 assists across 594 regular-season games since the Winnipeg Jets drafted him 25th overall in 2015. Nobody knows if Matthews had any actual pull in getting Roslovic to Toronto, but the connection between them looks real. Now it’s just a matter of seeing if it shows up on the scoresheet come October.
Figuring Out How to Build a Maple Leafs Roster
Chayka isn’t just collecting players who look good on a depth chart. He is trying to create a particular kind of team. For the first time in a while, I think that’s the question worth asking about almost every Maple Leafs move: Does this player fit what Toronto is becoming?
Toronto has spent years trying to find the right group of individual pieces. Chayka appears to be looking at the puzzle a little differently. Maybe the goal is to build a team with different kinds of experience, different kinds of players and, hopefully, a little more understanding of what it takes to win in April. Whether that works is still anybody’s guess. But at least there seems to be a plan behind the shopping list.
Free Newsletter
Get Toronto Maple Leafs coverage delivered to your inbox
In-depth analysis, breaking news, and insider takes - free.
Subscribe Free →