The sky is falling in Toronto, as the Toronto Maple Leafs disappointing season reaches a critical juncture. With the approaching trade deadline just around the corner, a losing streak out of the Olympic break hammers home the reality that the Leafs must sell. No doubt the coming days will be filled with rumours and speculation about what the Leafs could or should do.
Amongst the rumours, there is another team that seems to be linked to the Leafs for more than one player. The Edmonton Oilers are expected to be buyers, and the Leafs have several players that might be of interest. Oliver Ekman-Larsson and Bobby McMann have both been linked to the Oilers. Others, like Brandon Carlo, Scott Laughton, Nic Roy, or Anthony Stolarz, might even be better fits, though not as prevalent in the rumour mill.
Regardless, the Leafs should be looking to divest from the present, exchanging for future value. The team clearly wants to get back into the playoff picture as soon as possible, but they will need to get younger to truly improve. And their current prospect pool isn’t great. With that in mind, let’s take a look at some players the Leafs could target in a trade with the Oilers.
Salary counterweights and picks
To a certain extent, the Oilers will have to shed roughly as much salary as they add, and so any bigger trades will require the Leafs to take on some salary. Draft picks will likely be part of the equation as well, though mid to late round picks will not do the Leafs much good in the next two or three seasons. During that time, some older players who are underperforming their contracts will be easy to come by, if not necessary evils for the Leafs to acquire.
Andrew Mangiapane cap dump
From the Oilers perspective, Andrew Mangiapane is an obvious candidate. The winger has not fit well into the Oilers lineup. After some outstanding play under Brad Treliving with the Calgary Flames, Mangiapane was solid in a third-line role for the Washington Capitals. At his best, he can replicate those efforts with the Leafs, a scrappy winger who can help control play and add some reasonable scoring totals.
With another season on his contract after this, Mangiapane should be able to find a better fit. For example, Viktor Arvidsson struggled with the Oilers in a similar role last season, but has performed better this season on the Boston Bruins. Mangiapane will not bring the Leafs to a new stratosphere, but he could offer some help lower in the lineup.
Avoid Henrique and Frederic
The Oilers also have Adam Henrique, a pending UFA, who might be dangled as a counterbalance salary. After some strong work with the Oilers it appears Henrique’s effectiveness has diminished this season. He might have a bit more left, but Henrique might be in over his head as a third-line centre for an aspiring contender.
Moving off of Trent Frederic’s long extension would be a boon for the Oilers, but given his struggles and the length of his deal, this is not a contract the Leafs should be interested in. It would cost the Oilers a good deal to sweeten a Frederic trade. Between Mangiapane and Henrique, the Oilers can clear a good deal of space for deadline additions. These types of counterbalance salaries are necessary to their dealings more than they are of value to retooling efforts.
Defencemen
There are some notable defence prospects in the Oilers system, and the Leafs will have to be assertive in efforts to rebuild their blueline. It is not far-fetched to think that the Leafs will need to add their best defenceman before the team is able to turn things around. This type of defenceman is nearly impossible to acquire, and there are not necessarily strong candidates in the Oilers system.
There are, however, a few prospects that could be part of a solution for the Leafs: Alec Regula and Beau Akey. Both are right shots who have missed a good deal of time with injuries over the past few seasons.
Regula comes with experience and size
At 25 years old, Regula is the bigger and more experienced option. He has some NHL games under his belt, though his strong fancy stats were not reflected in his plus/minus this season. Though Regula has a lot of classic defensive traits, he does have an interesting combination of offensive tools as well. Regula seems to be a good passer and has produced respectable point totals in the AHL.
Given his injuries and his size, it might not be too surprising that Regula is a late bloomer. There continues to be some progression to his career, and he might be ready to push for a regular role as soon as next season. With his best hockey on the horizon, Regula represents an interesting option for the Leafs. The Leafs do not necessarily have a lot of time to wait for new prospects to help the NHL team, so an older option like Regula might be a nice balance.
Getting younger with Akey
Akey, on the other hand, is a bit younger. In his first season as a professional, Akey has posted respectable stats in the AHL. At times, he seems to be blocked for icetime, but it is still arguably his best performance since being drafted in 2023. At the time, his smooth skating was a big strength, and the thinking was that he would see a huge uptick in production with former OHL teammate Brandt Clarke leaving the team.
The OHL production did not improve. While there are certainly some offensive tools, it does not appear that Akey will score his way into the NHL. He will need a sound defensive game to continue rising up the ranks. Drafted by another regime, the Oilers might not be as patient with Akey as one might expect. There is clearly some progress to his game, and he would be a notable addition to the Leafs prospect pool, but it will require patience from the Leafs side of things as well.
Akey is further away from NHL action than Regula and is less likely to make it to that point as well. Of course, there are other notable prospects in the Oilers system, but Akey and Regula seem like preferred options for the Leafs.
Forwards
The Oilers seem to have targeted a glut of younger professionals, all in their early twenties. Matthew Savoie might have played his way into a different stratosphere, but there are a number of forwards on the cusp of regular NHL action. Again, this near-ripe youth is a way for the Leafs to get younger while still giving them a chance at roster help next season.
The recently acquired Isaac Howard might be a non-starter, but the Oilers still employ the quintet of Josh Samanski, Quinn Hutson, Connor Clattenburg, Roby Jarventie, and Viljami Marjala. All five could be players the Leafs find interesting, and all three might be able to push for an NHL spot next season.
Going through the options
Samanski is a big centre in his first AHL season, where he has adjusted nicely. His production is notable, but his straightforward style of game should translate well to the NHL. He looked capable in his brief NHL stint this season as well, and earned some confidence appearing for Germany at the Olympics.
Marjala is a centre of slighter frame. He projects less easily as a centre in the NHL, but clearly, he has some traits as a playmaking winger. Quinn Hutson has a similar profile as a smaller, skilled winger. Both have a strong sense of the game, but their smaller statures might scare some away.
Jarventie is a different style of winger, with a power element to his game. With size, speed, and a good shot, Jarventie’s physical traits have not seemed to translate into much growth. Clattenburg plays a different style of game, an energizer with an aggressive physical edge.
Maxim Berezkin should be the target
Perhaps the best forward option for the Leafs is a player not currently employed by the Oilers, as Maxim Berezkin is playing in the KHL. The big winger has always shown the speed and skill to be dangerous on the rush, attacking laterally and looking for passes, but has shown continued growth in some key areas.
Berezkin has the speed to get in on the forecheck and the skill to strip opponents off the puck. He has the strength and vision to make effective passes off the wall. Most importantly, he has shown a growing will to get to the net front.
If Berezkin comes to the NHL next season, he might be able to push for a regular spot. Perhaps it will take some time to adjust, but Berezkin has the tools to hit the ground running as a middle-six winger. There is, of course, no guarantee that Berezkin will do so, but at the very least, there is reason to believe he can.
Goalies
The Leafs do have a reasonably strong situation in net, as arguments can be made that both Dennis Hildeby and Artur Akhtyamov deserve some NHL games next season. Still, the Leafs could add value by investing in a goalie prospect. Despite their issues at the NHL level, the Oilers do seem to have many quality options in the system.
Connor Ungar has been incredible this season, and his age and proximity to the NHL might make including him in a trade less appealing to both the Leafs and the Oilers. Ungar seems to be on a similar timeframe to Hildeby and Akhtyamov. This might create too much of a glut in the Leafs system, which could ultimately be harmful to the progress of all three prospects.
Instead, the Leafs might look at some younger options that are further away. Samuel Jonsson played extremely well in Sweden last season, and to an extent, playing him in the ECHL is a curious decision. Nathaniel Day is playing in the ECHL as well. Eemil Vinni is playing in Finland. All three are some time away from NHL relevance, but could be divested from at a later point or give the Leafs peace of mind in potentially dealing away any of their goalies.
