If you’re a Toronto Maple Leafs fan, you’re likely hoping that general Brad Treliving’s second trade deadline is busier than his first.

The Leafs were in the thick of multiple rumours last season, as they always tend to be, but they didn’t do much to upgrade the roster. They re-acquired defenceman Ilya Lyubushkin from the Anaheim Ducks two years after trading for him the first time and kept their upgrades scarce on deadline day and in the days leading up to it. Defenceman Joel Edmundson was acquired from the Washington Capitals for a couple of draft picks, and forward Connor Dewar was acquired from the Minnesota Wild at the final buzzer for a late draft pick and a prospect.

Not that these guys haven’t contributed anything, but unless your team is firing on all cylinders and doesn’t have much room for upgrades, you’d like to see your team make a bigger splash at the deadline. The Leafs finished third in the Atlantic Division last season and easily could have used another middle-six forward rather than a depth forward and a pair of depth defencemen, but that’s in the past, and they have a chance to write their wrongs.

There have been a number of reports linking the Leafs to a pair of players from the Philadelphia Flyers, to different degrees. Scott Laughton has been directly linked to the Leafs as a trade target, and while there hasn’t been a formal report suggesting that the Leafs have checked in on Rasmus Ristolainen, the two parties have been linked to each other in the past. One of the reports stated that trading for Laughton would cost them a first-round pick or prospect Fraser Minten, which is a little hefty for somebody of Laughton’s calibre, but if there’s a way they can pull off a package deal to acquire both he and the hulking Finnish defenceman, Treliving should consider ponying up for it.

Let’s start with Laughton. While most years it seems the Leafs are in a market for a defenceman, they’re pretty set on the back end this year. Their main issue has been consistent depth scoring beyond the core four, and while Matthew Knies and Bobby McMann have stepped up nicely in this regard, they’re still lacking offence from players who were expected to contribute much more of it (Max Domi, Nick Robertson, etc). Laughton hasn’t exactly been a world-burner this season, with 11 goals and 26 points in 54 games, but he’s brought more to the table offensively than some of Toronto’s options. It’s not just the offence he brings, either. He leads all Flyers forwards in average penalty-kill TOI (time-on-ice) per game with an average of 1 minute and 41 seconds, and he’s got more hits than anyone on the Flyers not named Garnet Hathaway with 113, which would be second among Leafs forwards and fourth on the Leafs in general.

Laughton, 30, has spent his entire 11-year career with the Flyers and only has one meaningful playoff run to his name, but he was excellent in a depth role for the Flyers during that run, tallying five goals and nine points in 15 games in the bubble playoffs. He brings a ton of energy and plays that “playoff-style” game that Treliving has pushed for so often, and it also helps that while he’s most comfortable up the middle, he can play both wings too. He has one year left after this season on a five-year contract worth $3 million annually, which is a bargain for what he’s able to bring at his best and likely an attractive factor for the Leafs, who have voiced their desire to trade for players with term.

Let’s revisit the defensive corps. As I said, the Leafs are better positioned on defence than they have been in previous years. Jake McCabe and Chris Tanev are pretty clearly going to be their shutdown pair in the postseason, leaving Morgan Rielly and Oliver Ekman-Larsson as the other two locks for the playoff roster. That leaves Simon Benoit, Conor Timmins, and Philippe Myers as current contenders for the bottom pair. Benoit and Timmins have struggled mightily at points this season, and while Myers has been better, he shouldn’t be your fifth-best defenceman. In a perfect world, the Leafs get Jani Hakanpaa back and healthy (which may be a tall order at this point), and trade for a defenceman on the cheaper side who can allow Rielly to play his game and hold the fort in their own zone, think a Luke Schenn type. If you can swing that, you have the opportunity to pair either Myers or Hakanpaa with Oliver Ekman-Larsson on the bottom pair, which is the role that OEL played with the Florida Panthers on their Cup run last season.

Ristolainen has the disadvantage of name recognition working against him after a couple of rough years on an expensive contract, but credit where it’s due, he’s played some rock-solid hockey for John Tortorella’s Flyers. Although he isn’t as much of a two-way threat as he was projected to be early in his career, he’s rounded out his defensive game really nicely under Tortorella and seems like he would be a perfect complement to Rielly. He also falls under the requirement of having term on his deal, with two more years remaining at a price of $5.1 million.

Ristolainen is third on the team in hits, right behind Laughton, and logs the most time on the Flyers’ penalty kill after Travis Sanheim. His size and right-handed shot are both undoubtedly intriguing factors for Treliving and the Leafs, but how would they prepare a package? The biggest hurdle in this trade is the total salary involved coming back. The Leafs, who currently have just shy of $3 million to play with in cap space, would be taking $8.1 million in salary back with these two players, and while the fact that both players have term increases the likeliness of Toronto having interest in them, it also works against them in that you have to account for these contracts this summer and into next season. This while both Mitch Marner and John Tavares are up for new deals.

David Kampf would almost certainly be a contender to head the other way, with two years remaining on his contract at an average annual value (AAV) of $2.4 million. I would include Max Domi in here as well, who makes $3.75 million annually and has arguably been more disappointing than Kampf, but the reality of the Leafs trading Domi is low considering he’s in the first year of a four-year contract. This pretty much entirely writes off the possibility of the Leafs trading both, unless they’re able to swing the impossible. They do have other contenders for cap dumps, including Timmins and Ryan Reaves, and let’s be honest – the possibilities are endless with assistant general manager and ‘cap guru’ Brandon Pridham. This is one of those scenarios where I recognize my role as a Leafs writer and pass on the dirty work to the guy who’s paid to do it.

After that, you get to the actual asking price. The Leafs should be wary of parting with their 2026 first-round pick if it’s just for Laughton, but they should absolutely be dangling it if there’s an option to use it as a piece in a package deal. Dumping salary in the form of players like Kampf or Domi will add to the asking price as well, so the Leafs may have to ask themselves the tough question of whether these players are worth moving both a first and Minten for. In my opinion, when you consider what these players will be able to bring this season and beyond, it’s a hefty price but one worth paying, especially if it gets you out from underneath the dead cap space going back the other way.

Either way, the Leafs would be adding more than one player at this year’s deadline in a perfect world, and there’s an opportunity for them to check off their shopping list all in one deal. It will require some creativity, but we’ve seen them pull off creative deals in the past, and if they can bring the same energy here, they should go for it.