Friday Four: What can Maple Leafs learn from recent retools?

There weren’t many concrete statements that came out of Keith Pelley’s press conference from earlier this week. The president of MLSE took to the podium a day after relieving general manager Brad Treliving of his duties to address the path for the Toronto Maple Leafs going forward. 

Pelley touched on things like making sure a new front office has a focus on data and improving the culture, though much of that was vague and with the steps of how to get there unclear. However, where Pelley did leave no room for interpretation was about retooling the roster. He made it crystal clear the Leafs won’t be rebuilding, citing foundational pieces on the roster they can build around in Auston Matthews and William Nylander. 

It’s a bold proclamation to make without a general manager, and potentially without a president, in place. Toronto is devoid of draft capital and young prospects, has a roster full of holes and its biggest star is under contract for only two more seasons. Trying to make a bunch of potentially short-sighted moves to get Matthews to extend could be foolhardy and set the franchise back even further if things don’t work out. 

Even if it does seem challenging, organizations around the league pull it off all the time and make bold or under-the-radar moves to get them going back on the right trajectory. Let’s look at a few teams who have retooled recently and what elements or strategies they used to make it successful. 

Boston Bruins: Don’t settle for just picks

The Bruins seem like a good bet to get back to the playoffs this year after a rare miss last season. Part of their resurgence was fuelled by the Leafs themselves, thanks to the infamous Brandon Carlo trade at last year’s deadline that is quickly looking like a lopsided win for the Bruins. Boston received Toronto’s first-round pick this summer, which was only top-five protected. Based on where the Leafs are in the standings, that could end up being a massive get for the Bruins and something that might have ultimately doomed Treliving. 

However, the other part of the Carlo trade is what’s helping Boston at the moment. The talented, young Fraser Minten also came over from Toronto in the swap and he’s the Bruins' No. 1 centre. He’s probably not a top-line centre on a Cup contender, but Minten should develop into a solid two-way forward, nonetheless. They also brought back Casey Mittelstadt and Marat Khusnutdinov at last year’s deadline along with Minten. All three are under 28 years old, playing in Boston’s top six and will finish the season somewhere between 15-20 goals. Then there’s Viktor Arvidsson, who the Bruins acquired last summer for only a fifth-round pick. That small, low-risk investment has netted them 24 goals and counting. 

Boston used the 2025 trade deadline to get younger and refresh its roster immediately, instead of just pursuing future draft picks. The Bruins haven’t even made the picks they got back for Carlo and Brad Marchand yet, but Minten, Khusnutdinov and Mittelstadt are already helping. This is perhaps a misstep the Leafs made a few weeks ago, when they sold off a few pieces if they were eyeing a retool. The Leafs got only picks back for Nic Roy, Scott Laughton and Bobby McMann, instead of at least a couple of players who might be able to contribute as early as next season. 

Toronto could take this lesson with it into the off-season, though. If the new regime decides to move on from Nick Robertson, Matias Maccelli, Max Domi or Simon Benoit, let's say, the Leafs could try to target a player who has maybe fallen out of favour with their organization instead of a late-round pick. Use your scouting department to identify someone who freshens up your roster, even if they only end up playing in your middle or bottom six. In a retool situation, a player like that will be more valuable than a draft pick that has a slim chance of turning into anything years down the line. 

Pittsburgh Penguins: Walking a fine line

Ironically, one of the best options to lead the Leafs through a retool might be Treliving’s predecessor. Kyle Dubas has done a masterful job putting the Penguins in a spot to qualify for the playoffs this spring after three years out. 

Pittsburgh's and Toronto’s situations have some similarities. The Penguins were trying to make the team more competitive in hopes of giving Sidney Crosby another playoff run, but while also simultaneously building for the future. Dubas has walked that fine line well and the Leafs might have to do something similar when it comes to Matthews. If the idea is to improve the team so Matthews signs an extension, what happens if it doesn’t work? You don’t want to invest more significant draft capital, term or cap dollars in the team if Matthews ends up leaving in a year anyway, and then you’re in an obvious rebuild. 

Dubas' Penguins still have all their first-round picks in the next four drafts and have accumulated a combined 15 selections over the second and third rounds over that span, while adding key pieces to the roster at the same time. He’s done so by finding hidden gems and buying low on players who fit into the Penguins' future timeline, who can also help them today. Drafting Ben Kindel 11th overall last year didn’t hurt either. Kindel has been a huge contributor for the Pens, with 17 goals and holding down a middle-six centre spot all season. 

As far as the additions go, Anthony Mantha, Parker Wotherspoon and Yegor Chinakhov have been found money. Dubas signed Mantha to a one-year, $2.5-million deal last summer, which was a win-win situation for the Pens. In a worst-case scenario, Pittsburgh could’ve shipped Mantha off at the deadline for a draft pick, but in a best-case scenario, he’s scored 30 goals for the Pens this season and has been one of their best forwards. Wotherspoon was inked for two years with a $1-million AAV and is averaging more than 20 minutes a night next to Erik Karlsson on Pittsburgh’s top pair. Meanwhile, Chinakhov, who was floundering in Columbus, has scored 17 goals in 38 games since arriving in Pittsburgh. 

None of those acquisitions were risky, cost much or took anything away from the Pens future. The Leafs need to look for a few of those this off-season that may come cheap and could have an immediate impact. Someone like Frank Vatrano, who had 80 goals over the previous three seasons, doesn’t seem to be a favourite of Joel Quenneville's in Anaheim. His ice time and role have dropped significantly. Dmitri Voronkov, who has been scratched recently in Columbus, is a big body who can score and is still only 25. Could either of them be had for a reasonable price? Both Voronkov and Vatrano could jolt the roster and wouldn’t be anchors if the Leafs have to eventually tear it all down after all. 

New York Islanders: Flipping a switch overnight

Let’s be blunt. The Isles have really only turned things around because of an improbable lottery win last year that landed them Matthew Schaefer. New York had just a 3.5 per cent chance to secure the No. 1 pick, but the lottery balls landed in their favour and now they appear to be on a rapid ascension after attaching themselves to Schaefer’s rocket ship. The 2024-25 Islanders felt like one of the stalest teams in the league but virtually overnight they’ve become one of its most exciting, thanks to Schaefer. 

The reason I mention the Islanders here is because Toronto’s first-round pick in June in tenuously hanging in the balance. If the Leafs fall anywhere outside the top five, the pick goes to Boston in the aforementioned Carlo deal, but if they sit inside the top five after the lottery, they get to keep it. Pelley was steadfast in his stance that the Leafs won’t tank, though if you watch the impact Schaefer and Macklin Celebrini have had this season, it seems paramount the Leafs do everything they can to keep their selection. 

Now, that would mean the Leafs would lose their first-round pick in the 2027 and 2028 drafts if they keep it this year, but it could be worth it. The first few projected 2026 picks could be major difference-makers, and if you could get one of Ivar Stenberg, Gavin McKenna, Chase Reid or Keaton Verhoeff, they may be able to help the Leafs as soon as next season. Banking on one of them now would be a wise move because the next two drafts may not be as deep or strong. 

There’s a difference between tanking and doing what makes the most sense for a franchise’s long-term future. The Florida Panthers have been beaten up from a long season and three deep playoff runs in a row, so they are shutting down several key players for the remainder of the season to help ensure they finish in the bottom 10 to keep their pick. Those players are no doubt banged-up, so why not get a look at some younger Panthers and let those established talents get an earlier start on the off-season.

No one is advocating for losing intentionally, although the Leafs could be using this same strategy as the Panthers in some situations. Matthew Knies has been battling something all season that gets better rest, so why not give him a night off here and there, and see what you have in a couple of AHL players. Or, better yet, do John Tavares and Nylander still need to be playing 20-plus minutes a night in a lost season? 

The Leafs are three points up on fifth-to-last, even after winning three of their past five games. While there are no guarantees in the lottery, giving themselves the best odds at landing a top-five pick over the final half dozen games could be pivotal to the future of the franchise. 

Florida Panthers: Being bold and aggressive

OK, hear me out on this one. The Panthers might not be the first team that comes to mind when you think retool, but they are arguably the best example of it in recent memory. A retool doesn’t just have to apply to a team that has taken a step back and Florida reshaped its roster over the past few years despite being a perennial playoff team. 

Panthers general manager Bill Zito took over before the 2020-21 season and has consistently been adding to the roster ever since. He started by signing Carter Verhaeghe for pennies on the dollar, bought low on Sam Bennett and claimed Gustav Forsling on waivers. But even though the Panthers were improving quickly, Zito wasn’t satisfied. After winning the Presidents’ Trophy following the 2021-22 campaign, he replaced head coach Andrew Brunette with Paul Maurice and traded a 115-point player in Jonathan Huberdeau for Matthew Tkachuk. If that’s not a retool, I don’t know what is. 

Granted, Florida did a lot of its heavy lifting in a different landscape. The Panthers built much of their roster through trades and free-agent signings, capitalizing on players teams had to offload in a flat-cap world. Free agency is becoming thinner and thinner every year, with teams prioritizing keeping their own players, and with the cap now rising, there will be fewer impact cap casualties for organizations to pounce on. 

Still, Zito’s bold mentality can still be channelled today. Despite having some success, he didn’t believe the Panthers couldn’t win the Cup with the status quo and wanted to create a different culture. Since then, Florida has been unstoppable in the playoffs and has become the toughest team to play against. Trading Huberdeau was risky but Zito obviously felt it was worth it. The new front office in Toronto will have to ask similar questions. Can the Leafs still win by building a team around the foundational pieces Pelley was referring to?

Someone like Nylander has been polarizing throughout his time with the Leafs. Nylander possesses immense skill and talent but will his indifferent and nonchalant nature at times conflict with the new culture a front office will try to create? He has full trade protection, and this isn’t to advocate for a deal, though he’s closing in on 30 and would undoubtedly return a haul if he was available. If the Leafs could make a hockey trade involving Nylander and return a top-pair defenceman and a young second-line centre, is that something they would consider?

These are uncomfortable conversations, but the Leafs are in the position they are in now because they’ve been petrified of change and leaned on complacency. Florida has gone the opposite route and the Panthers' boldness in overhauling their roster has taken them to another level.

Anytime you make significant changes within your organization, it’s going to come with risk, and the Leafs will have to decide how much of it they are willing take.