The Leafs should make another trade with the Penguins

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If there’s one thing I love about the NHL offseason, it has to be the immediate fallout of a big trade and watching both the fans of either team or neutral observes react to it. Trades are stupid fun and there’s nothing more enjoyable in sports than going over a recent transaction and trying to determine the winners and losers before either player has participated in a single game with their new organization.

Wednesday morning saw the latest example as a team the Leafs traded with weeks ago made an interesting deal with the Florida Panthers.

At the time of writing this post, this trade has yet to go through due to a combination of a glitch, Patric Hornqvist not answering his phone, and insurance issues related to injuries. I wish I was making all of this up, but it’s true.

We have all seen the occasional blunder of a transaction from a general manger because not everyone is perfect (that includes Kyle Dubas). If you have been paying any attention to the Pittsburgh Penguins over the last few years, this potential trade appears to be the latest example of Jim Rutherford making a questionable deal without considering the long-term implications of it.

That is why it might be a good idea for the Leafs to try and make another trade with the Penguins in the coming weeks.

Back in August, the Leafs and Penguins agreed to a massive deal that saw Kasperi Kapanen return to the team that drafted him. Toronto got back a quality prospect, two depth pieces, and a first-round pick. On the surface, this looks like a trade that saw one team look to upgrade their forward depth and the other get some assets back from a player they no longer needed. But it’s the package that Pittsburgh surrendered in order to Kapanen that could have the makings of backfiring on them years down the line.

Unless you have been living under a boulder, the Penguins still have Sidney Crosby and Evgeni Malkin on their roster. Both players are nearing the end of their primes and only have a few more years left of quality play before an inevitable decline begins. Given that they are three years removed from their most recent Stanley Cup victory, it makes sense why Rutherford would be interested in trying to put his team in position for one last crack at winning a title before beginning a rebuild. One drawback of going on this path is that the assets surrendered in any potential transaction may come back to haunt the team years down the line when the window of contention closes and the next chapter of the franchise begins. That’s because the players and the draft picks traded away might find themselves in the NHL and could be having success, leaving the other team pondering what could have been had they held onto the asset instead of giving it away for short-term fixes.

The Penguins chose to try and keep their contention window open for as long as they can and it has resulted in some trades and signings that have left their fanbase baffled at times. For instance, they shipped off a third-round pick to the San Jose Sharks in exchange for Leafs legend Patrick Marleau. He produced just two points in eight regular-season games and went scoreless in the playoffs. Then there’s the nixed deal that would have seen Phil Kessel going to the Minnesota Wild in exchange for a package that included Jason Zucker. Kessel ended up getting dealt to the Arizona Coyotes for Alex Galchenyuk, leaving Penguins fans wondering which trade would have been better.

While we’re on the subject of Zucker, he was one of the bright spots in the latter half of the 2019-20 season before the pause, but Pittsburgh had to give up Galchenyuk and a first-round pick in 2021 to acquire his services. Combined with giving up this year’s first to bring back Kapanen, that means the Penguins won’t have a first-round pick until 2022. In fact, they have only maintained their first-round pick twice dating back to 2013. Want to know which of their first-round picks since 2007 has had the best NHL career so far? Kasperi Kapanen, who had spent the entirety of it on the Leafs prior to the trade.

No dissection of the Penguins transactions over the last few years would be complete without going over the two signings Rutherford made on the first day of free agency in 2018 and 2019. Jack Johnson is a guy their fan base has had gripes with from the moment he put pen to paper. The decision to sign Brandon Tanev a year ago was widely panned at the time, though he did go on to have a solid season with his new team. And now there are rumours that the Penguins intend on signing Chris Tanev should he become a free agent and who knows what the reaction will be if it transpires.

This brings us back to the Leafs and their continued search for making improvements to their blueline and figuring out who will be their starter of the future. I have no clue what the relationship between Dubas and Rutherford is like, but I have to imagine they are on good terms after the Kapanen trade.

Matt Murray has reportedly been connected to Toronto for the past few weeks. Although the Penguins don’t have the most coveted blue line in the NHL, John Marino had a solid rookie season that saw him finish eighth in the Calder Trophy voting. By no means am I suggesting that Rutherford is desperate to move either of those assets right now, but either one of the aforementioned players would be a solid addition in the Leafs roster. It would be in Toronto’s best interest to consider giving Pittsburgh a call and inquire about players like Murray and Marino, especially if Pittsburgh’s asking price is reasonable.

In the case of Marino, who wouldn’t want to try and add a player that can pull off moves like this:

So why should the Leafs make another trade with the Penguins? Their G.M. appears determined to get the most out of the final years of Crosby and Malkin’s prime, whether that be making a big splash in free agency or sacrificing youth in exchange for immediate help. Toronto is also trying to contend but could certainly use a fresh set of faces on defence and in net for the upcoming season and beyond. Both teams have already made a trade with each other weeks ago and appear to be on good terms. Put it all together, and you get a perfect storm that Toronto (and the rest of the league for that matter) has to take full advantage of.

After today’s probable trade between Pittsburgh and Florida, Dubas needs to strike while the iron is hot and give Rutherford a call about doing another deal.