Although the 2023 playoffs ultimately ended in disappointment for the Leafs, two players that made a significant impact on the team finally getting past the first round were Ryan O&#8217;Reilly and Noel Acciari.
Both were the two key pieces acquired in a blockbuster trade that involved numerous futures heading to the Blues which included their 2023 first-round pick. Each of them provided an element of their games that was sorely lacking from the team prior to their arrival. And with both players on expiring contracts and unsigned at the time of writing, they present the organization with a dilemma of whether or not to keep them.
The Leafs had to include a third team in the Wild to help make the salary work as a pure 50% retention would not have been enough given that no one on the main roster was included in the trade. However, there was a player on the active roster who was nearly included in the trade that would have eliminated the need for the third team: Alex Kerfoot.
Joshua Kloke mentioned in his piece <a href="https://theathletic.com/4551455/2023/05/26/maple-leafs-free-agents/" target="_blank" rel="noopener">about where things stand with the Leafs&#8217; pending free agents</a> that Kerfoot could have been part of the return package in the O&#8217;Reilly-Acciari trade but Dubas wanted to keep the forward and thus needed to get the Wild involved at the cost of a 2025 fourth-round pick.
It reiterates a report that Elliotte Friedman brought up during <a href="https://podcasts.apple.com/ca/podcast/32-thoughts-the-podcast/id1332150124?i=1000602753273" target="_blank" rel="noopener">an episode of 32 Thoughts: The Podcast released on March 4th</a> where he said the following:
<blockquote>Toronto did that deal with St. Louis through Minnesota to keep Kerfoot. And that&#8217;s why I wasn&#8217;t surprised that Kerfoot wasn&#8217;t traded. Toronto could have done that deal with St. Louis themselves, but they asked Minnesota to retain an extra 25% on O&#8217;Reilly and paid the pick to keep Kerfoot.</blockquote>
There were also <a href="https://dailyhive.com/vancouver/alex-kerfoot-canucks-leafs-trade-rumour" target="_blank" rel="noopener">rumours around that time</a> that Kerfoot could have been dealt to the Canucks after the Leafs acquired Jake McCabe and Sam Lafferty, but that move ultimately did not materialize either. Kerfoot made it through the deadline and thus spent the rest of the season primarily in Toronto&#8217;s bottom six, where he recorded seven points in the final 27 games before scoring twice in the playoffs including the Game 4 OT winner.
Whether or not you agree with Dubas&#8217; decision to hold onto Kerfoot through the 2023 trade deadline, the implications that trading him would have had on the lineup and some future events are quite fascinating.
Had he been sent to St. Louis in a cap dump, the Leafs likely would have called up a player or two from the Marlies to fill the void left behind. My best guess is that they would have been Pontus Holmberg and Bobby McMann, both of whom impressed during their earlier stints with the team during the regular season. Given that McMann would subsequently <a href="https://thehockeynews.com/nhl/toronto-maple-leafs/news/maple-leafs-bobby-mcmann-to-miss-some-time-after-re-injuring-knee" target="_blank" rel="noopener">re-aggravate a knee injury</a> in the AHL a few weeks after the deadline, it&#8217;s possible that he could have been healthy the rest of the way and might have been able to slot in when Matthew Knies suffered a concussion in Game 2 vs the Panthers.
By no means would the younger options have been guaranteed to fare better than Kerfoot&#8217;s seven points to close out the regular season, but perhaps having the younger options available could have yielded a different outcome as the playoffs went along. It could have also helped out immensely with the development of players like Holmberg and McMann being put in high-pressure situations. Perhaps shipping out Kerfoot would have also prevented the Leafs from being caught in a tricky cap situation in the final week of the regular season after signing Knies.
As mentioned earlier, Kerfoot was the guy who scored the overtime winner in Game 4 against the Lightning, which was the exclamation mark of their dramatic 4-1 comeback victory. I can understand why some would therefore believe that giving up the fourth-round pick was worth it. Logic would tell you that when you are trying to win now, you have to give up future assets such as draft picks for the sure thing. Dubas likely thought that this future player won&#8217;t be selected for another two years and that it will take at least five seasons afterwards to find out whether surrendering the pick was the right move, hence why he was comfortable including a third team in the trade.
With Kerfoot&#8217;s versatility to move up and down the lineup, his two-way play, and being a season removed from a career year, I can understand why Dubas opted to keep the forward instead of including him in the O&#8217;Reilly-Acciari trade. The Leafs got stronger once the deal was made and losing Kerfoot would have had an impact on the team&#8217;s overall play. The rationale for GMs in win-now mode is that you try to make a trade that allows you to improve the team and not take someone off the roster as a result.
Having said that, sending Kerfoot to the Midwest also could have also had a lot of benefits for the Leafs. His $3.5 million cap hit being off the books would result in an asset being saved for future use, their younger players would have had a path to get on the roster and continue their development, and signing Knies would not have been as complicated as it wound up being. That fourth-round pick obviously would not have scored the overtime winner in Game 4, but it also does not make much sense to get rid of a draft pick in that manner when the player they protected is likely going to walk into free agency anyway.
Regardless, Kerfoot wound up remaining on the roster through the end of the regular season and helped contribute to the Leafs overcoming their first-round demons with an OT winner. Had the return package of one of the biggest trades of this era looked slightly different, who knows how much would have changed when Mark Giordano fired a point shot on the power play in Game 4.
Stats from <a class="text-accent" href="https://www.hockey-reference.com/" target="_blank" rel="noopener noreferrer external nofollow" data-wpel-link="external">Hockey-Reference.com</a> and <a class="text-accent" href="http://naturalstattrick.com/" target="_blank" rel="noopener noreferrer external nofollow" data-wpel-link="external">Natural Stat Trick</a>.
<div>Salary information from <a href="https://www.capfriendly.com/" target="_blank" rel="noopener noreferrer external nofollow" data-wpel-link="external">CapFriendly.</a></div>

Although the 2023 playoffs ultimately ended in disappointment for the Leafs, two players that made a significant impact on the team finally getting past the first round were Ryan O'Reilly and Noel Acciari.

Both were the two key pieces acquired in a blockbuster trade that involved numerous futures heading to the Blues which included their 2023 first-round pick. Each of them provided an element of their games that was sorely lacking from the team prior to their arrival. And with both players on expiring contracts and unsigned at the time of writing, they present the organization with a dilemma of whether or not to keep them.

The Leafs had to include a third team in the Wild to help make the salary work as a pure 50% retention would not have been enough given that no one on the main roster was included in the trade. However, there was a player on the active roster who was nearly included in the trade that would have eliminated the need for the third team: Alex Kerfoot.

Joshua Kloke mentioned in his piece <a href="https://theathletic.com/4551455/2023/05/26/maple-leafs-free-agents/" target="_blank" rel="noopener">about where things stand with the Leafs' pending free agents</a> that Kerfoot could have been part of the return package in the O'Reilly-Acciari trade but Dubas wanted to keep the forward and thus needed to get the Wild involved at the cost of a 2025 fourth-round pick.

It reiterates a report that Elliotte Friedman brought up during <a href="https://podcasts.apple.com/ca/podcast/32-thoughts-the-podcast/id1332150124?i=1000602753273" target="_blank" rel="noopener">an episode of 32 Thoughts: The Podcast released on March 4th</a> where he said the following:
<blockquote>Toronto did that deal with St. Louis through Minnesota to keep Kerfoot. And that's why I wasn't surprised that Kerfoot wasn't traded. Toronto could have done that deal with St. Louis themselves, but they asked Minnesota to retain an extra 25% on O'Reilly and paid the pick to keep Kerfoot.</blockquote>
There were also <a href="https://dailyhive.com/vancouver/alex-kerfoot-canucks-leafs-trade-rumour" target="_blank" rel="noopener">rumours around that time</a> that Kerfoot could have been dealt to the Canucks after the Leafs acquired Jake McCabe and Sam Lafferty, but that move ultimately did not materialize either. Kerfoot made it through the deadline and thus spent the rest of the season primarily in Toronto's bottom six, where he recorded seven points in the final 27 games before scoring twice in the playoffs including the Game 4 OT winner.

Whether or not you agree with Dubas' decision to hold onto Kerfoot through the 2023 trade deadline, the implications that trading him would have had on the lineup and some future events are quite fascinating.

Had he been sent to St. Louis in a cap dump, the Leafs likely would have called up a player or two from the Marlies to fill the void left behind. My best guess is that they would have been Pontus Holmberg and Bobby McMann, both of whom impressed during their earlier stints with the team during the regular season. Given that McMann would subsequently <a href="https://thehockeynews.com/nhl/toronto-maple-leafs/news/maple-leafs-bobby-mcmann-to-miss-some-time-after-re-injuring-knee" target="_blank" rel="noopener">re-aggravate a knee injury</a> in the AHL a few weeks after the deadline, it's possible that he could have been healthy the rest of the way and might have been able to slot in when Matthew Knies suffered a concussion in Game 2 vs the Panthers.

By no means would the younger options have been guaranteed to fare better than Kerfoot's seven points to close out the regular season, but perhaps having the younger options available could have yielded a different outcome as the playoffs went along. It could have also helped out immensely with the development of players like Holmberg and McMann being put in high-pressure situations. Perhaps shipping out Kerfoot would have also prevented the Leafs from being caught in a tricky cap situation in the final week of the regular season after signing Knies.

As mentioned earlier, Kerfoot was the guy who scored the overtime winner in Game 4 against the Lightning, which was the exclamation mark of their dramatic 4-1 comeback victory. I can understand why some would therefore believe that giving up the fourth-round pick was worth it. Logic would tell you that when you are trying to win now, you have to give up future assets such as draft picks for the sure thing. Dubas likely thought that this future player won't be selected for another two years and that it will take at least five seasons afterwards to find out whether surrendering the pick was the right move, hence why he was comfortable including a third team in the trade.

With Kerfoot's versatility to move up and down the lineup, his two-way play, and being a season removed from a career year, I can understand why Dubas opted to keep the forward instead of including him in the O'Reilly-Acciari trade. The Leafs got stronger once the deal was made and losing Kerfoot would have had an impact on the team's overall play. The rationale for GMs in win-now mode is that you try to make a trade that allows you to improve the team and not take someone off the roster as a result.

Having said that, sending Kerfoot to the Midwest also could have also had a lot of benefits for the Leafs. His $3.5 million cap hit being off the books would result in an asset being saved for future use, their younger players would have had a path to get on the roster and continue their development, and signing Knies would not have been as complicated as it wound up being. That fourth-round pick obviously would not have scored the overtime winner in Game 4, but it also does not make much sense to get rid of a draft pick in that manner when the player they protected is likely going to walk into free agency anyway.

Regardless, Kerfoot wound up remaining on the roster through the end of the regular season and helped contribute to the Leafs overcoming their first-round demons with an OT winner. Had the return package of one of the biggest trades of this era looked slightly different, who knows how much would have changed when Mark Giordano fired a point shot on the power play in Game 4.

Stats from <a class="text-accent" href="https://www.hockey-reference.com/" target="_blank" rel="noopener noreferrer external nofollow" data-wpel-link="external">Hockey-Reference.com</a> and <a class="text-accent" href="http://naturalstattrick.com/" target="_blank" rel="noopener noreferrer external nofollow" data-wpel-link="external">Natural Stat Trick</a>.
<div>Salary information from <a href="https://www.capfriendly.com/" target="_blank" rel="noopener noreferrer external nofollow" data-wpel-link="external">CapFriendly.</a></div>

Report: Alex Kerfoot was nearly part of the Ryan O’Reilly-Noel Acciari trade

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