We&#8217;ve made it through August. Finally. The darkest month for hockey content is over and by next week we&#8217;ll have prospect camps, the following week we&#8217;ll be treated to rookie tournaments, and soon training camps will open. NHL hockey is slowly returning.
While the return of hockey and things hockey related to talk about is more than welcome, it does begin to attach a bit of a sense of urgency to some of the things left for the Leafs to address, and right at the top of the list has to be dealing with the contract for @Morgan Rielly.
One of the things that has been an ongoing area that Kyle Dubas needs to improve in is addressing the amount of talent that has walked out the door in free agency with no returning asset for the Leafs beyond having a bit more cap space to work with in the offseason.
Kyle Dubas became the GM of the Leafs in May of 2018. That first offseason is a bit more forgivable as it would have been Lou Lamoriello failing to extend James van Riemsdyk and Tyler Bozak, but nevertheless it was on Dubas&#8217; watch that JVR and Bozak left the Leafs without Toronto receiving a return. The following offseason Jake Gardiner would be the marquee player that would fail to be re-signed and would leave the Leafs on the open market. The summer of 2020 was a bit more forgivable, but again Tyson Barrie and Cody Ceci would leave the Leafs organization without an asset in return, and given that both were brought in with one season remaining on their deal, it&#8217;s understandable, but given their performance as Leafs, moving them at the deadline would have been equally understandable and instead emphasizes an exodus of name brand talent without so much as a draft pick in return.
This current offseason saw more of the same, and while the Leafs took an &#8220;All or Nothing&#8221; stance on their season, the decision to risk letting pending UFA assets like Frederik Andersen and Zach Hyman walk for nothing was another failed gamble. The third failed gamble under Kyle Dubas, and the fourth we&#8217;ve seen with the revitalized Leafs (that 2017 playoff run needs to be treated as a found wallet.)
Now here we are with Morgan Rielly, unquestionably the best asset of the pending UFAs the Leafs have risked bringing to market. Whether you like Rielly&#8217;s style of play or not, he has been the Leafs&#8217; number one defenseman. He is a valued player around the NHL, and he is someone who could command a Dougie Hamilton sized contract on the open market and could very well require a John Carlson type extension in order to keep him around. An expensive reality, and even if Rielly takes a team friendly deal, it&#8217;s going to be a significant raise, and might come with a term length that is worrisome.
While getting the extension done in the offseason doesn&#8217;t eliminate the possibility of it being done in season, things only get more complicated the longer it takes. An extension at any point has the same effect, but the Leafs lose a lot of trade leverage as teams finalize their rosters, and with the number of maxed out salary cap teams in the NHL, even Morgan Rielly&#8217;s very team friendly $5M cap hit becomes increasingly difficult to move. The reality is the Leafs could find themselves in a very familiar place at the trade deadline where they have a still unsigned top of the roster talent, and a team and fan base that wants to believe it&#8217;s in their best interest to keep Rielly as an &#8220;own rental&#8221; player a playoff run.
The Leafs are in the unfortunate situation of wanting to keep Rielly, but dealing with the complex realities of their salary cap situation, which isn&#8217;t going to improve. They also are presented with an offseason where there doesn&#8217;t seem to be enough defensemen to go around. The Leafs aren&#8217;t really a team that can sacrifice defensive depth, but given the offensive nature of Rielly&#8217;s game they might be more comfotable moving on. Rielly being traded means there wouldn&#8217;t be a whole lot of defensive zone trade off, but immediately the Leafs 5v5 transition game takes a giant step backward.
Rielly is represented by J.P. Barry, who isn&#8217;t short on clients, and has four other clients on the Leafs, so there&#8217;s absolutely a good working relationship with Toronto. Barry also has a history of reasonable contracts, like the Pastrnak deal, Klefbom in Edmonton, but he also just got his other client Dougie Hamilton a $9M AAV deal with a role remarkably similar to Rielly&#8217;s. Basically it will be team friendly or it won&#8217;t be.
The Leafs are as silent as ever about whether there is any progress, but at the same time there hasn&#8217;t been any mention of Rielly in trade rumours either. With August vacations over we might begin hearing more about this important contract, but for now we just know that Rielly should be an organizational priority.

We've made it through August. Finally. The darkest month for hockey content is over and by next week we'll have prospect camps, the following week we'll be treated to rookie tournaments, and soon training camps will open. NHL hockey is slowly returning.

While the return of hockey and things hockey related to talk about is more than welcome, it does begin to attach a bit of a sense of urgency to some of the things left for the Leafs to address, and right at the top of the list has to be dealing with the contract for @Morgan Rielly.

One of the things that has been an ongoing area that Kyle Dubas needs to improve in is addressing the amount of talent that has walked out the door in free agency with no returning asset for the Leafs beyond having a bit more cap space to work with in the offseason.

Kyle Dubas became the GM of the Leafs in May of 2018. That first offseason is a bit more forgivable as it would have been Lou Lamoriello failing to extend James van Riemsdyk and Tyler Bozak, but nevertheless it was on Dubas' watch that JVR and Bozak left the Leafs without Toronto receiving a return. The following offseason Jake Gardiner would be the marquee player that would fail to be re-signed and would leave the Leafs on the open market. The summer of 2020 was a bit more forgivable, but again Tyson Barrie and Cody Ceci would leave the Leafs organization without an asset in return, and given that both were brought in with one season remaining on their deal, it's understandable, but given their performance as Leafs, moving them at the deadline would have been equally understandable and instead emphasizes an exodus of name brand talent without so much as a draft pick in return.

This current offseason saw more of the same, and while the Leafs took an "All or Nothing" stance on their season, the decision to risk letting pending UFA assets like Frederik Andersen and Zach Hyman walk for nothing was another failed gamble. The third failed gamble under Kyle Dubas, and the fourth we've seen with the revitalized Leafs (that 2017 playoff run needs to be treated as a found wallet.)

Now here we are with Morgan Rielly, unquestionably the best asset of the pending UFAs the Leafs have risked bringing to market. Whether you like Rielly's style of play or not, he has been the Leafs' number one defenseman. He is a valued player around the NHL, and he is someone who could command a Dougie Hamilton sized contract on the open market and could very well require a John Carlson type extension in order to keep him around. An expensive reality, and even if Rielly takes a team friendly deal, it's going to be a significant raise, and might come with a term length that is worrisome.

While getting the extension done in the offseason doesn't eliminate the possibility of it being done in season, things only get more complicated the longer it takes. An extension at any point has the same effect, but the Leafs lose a lot of trade leverage as teams finalize their rosters, and with the number of maxed out salary cap teams in the NHL, even Morgan Rielly's very team friendly $5M cap hit becomes increasingly difficult to move. The reality is the Leafs could find themselves in a very familiar place at the trade deadline where they have a still unsigned top of the roster talent, and a team and fan base that wants to believe it's in their best interest to keep Rielly as an "own rental" player a playoff run.

The Leafs are in the unfortunate situation of wanting to keep Rielly, but dealing with the complex realities of their salary cap situation, which isn't going to improve. They also are presented with an offseason where there doesn't seem to be enough defensemen to go around. The Leafs aren't really a team that can sacrifice defensive depth, but given the offensive nature of Rielly's game they might be more comfotable moving on. Rielly being traded means there wouldn't be a whole lot of defensive zone trade off, but immediately the Leafs 5v5 transition game takes a giant step backward.

Rielly is represented by J.P. Barry, who isn't short on clients, and has four other clients on the Leafs, so there's absolutely a good working relationship with Toronto. Barry also has a history of reasonable contracts, like the Pastrnak deal, Klefbom in Edmonton, but he also just got his other client Dougie Hamilton a $9M AAV deal with a role remarkably similar to Rielly's. Basically it will be team friendly or it won't be.

The Leafs are as silent as ever about whether there is any progress, but at the same time there hasn't been any mention of Rielly in trade rumours either. With August vacations over we might begin hearing more about this important contract, but for now we just know that Rielly should be an organizational priority.

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