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Brad Treliving is getting his first taste of the Stanley Cup Playoffs as general manager of the Toronto Maple Leafs and needless to say, he can’t be too pleased with the dish. The 2024 offseason is shaping up to be one for the ages.

Treliving tried to put his fingerprints on the team immediately upon taking the gig. He brought in pi-- and vinegar. He found some snot for the Leafs lineup. Unfortunately, while it’s added another element to the roster, it hasn’t worked out one bit. Toronto is down 3-1 to the big bad Boston Bruins and two of Treliving’s free-agent signings, Max Domi and Ryan Reaves have been brutal. Undisciplined penalties, costly turnovers, Domi and Reaves continue to impact each loss for all the wrong reasons. The rest of the team shouldn’t be given a pass either.

The Bruins’ stars have outplayed the Maple Leafs best and when your best players aren’t playing like your best players during the biggest games of the season, it’s never a recipe for success. Treliving has his work cut out for him this upcoming offseason as it certainly feels like this Leafs team has no chance of beating the Bruins in three straight to keep their dreams alive.

Where does Treliving go from here? With Joseph Woll the likely starter for Game 5 after making his series debut starting the third period of Game 4, Ilya Samsonov might as well pack his bags. The Russian netminder had a rough season, found his groove after being reset and now, has unfortunately let in a series of soft goals throughout the first four games. As a pending free agent, Treliving is likely to thank Samsonov for his service and let him walk come July.

Sheldon Keefe is on the hot seat, even with an extension in his back pocket. Treliving will have to think long and hard if Keefe and his entire staff are the right group to lead the Leafs squad. Special teams have been a huge storyline so far these playoffs and while it certainly comes down to the players executing, the coaching staff’s structure will be under the microscope this summer. It will be interesting to see if Treliving comes out after the season to give Keefe a vote of confidence or if he’ll give the expected response that everything will be fully evaluated in due time.

Then there’s the core. Treliving has committed long-term to Auston Matthews and William Nylander and both aren’t going anywhere. Morgan Rielly also staying put. John Tavares will enter the final season of his current deal and can be re-signed come July 1st. It does seem like Tavares would be open to a hometown discount to stick around and finish his career in Toronto. Would a three-year deal at $5 million per season be enough to get both sides to agree? Certainly, a storyline to follow this summer.

Now to the main event. Mitch Marner has been under the microscope these playoffs, more than any other Maple Leaf. From consistently losing puck battles, to a lack of effort on the penalty kill that led to a back-breaking Bruins’ goal in Game 4,  Marner is getting chirped from every angle at the moment. Even his teammates have been involved in the chatter as things got ugly in Game 4. Nylander was seen telling Marner to stop crying which then led to Marner throwing his gloves down behind the bench in frustration. While they both said it’s nothing but love and they just care a lot and want to win, Treliving has a major decision to make should the Maple Leafs not pull off a miracle and come back against the Bruins. Should he offer Marner an extension or ask him for a list of teams he’d approve a trade to? Decisions, decisions.

After being given the benefit of the doubt for almost a decade and with some progress last playoffs with a first-round series win, it’s become evident this core isn’t it. Treliving would be smart to see what the trade market looks like for Marner this summer, take a page out of the Toronto Raptors book and move a star for a star. Kawhi Leonard brought a championship to Toronto and the Maple Leafs GM needs to find himself his own Kawhi. Easier said than done.

Is it a goalie? Juuse Saros could be available and could Marner be open to reuniting with Ryan O’Reilly and Luke Schenn in Nashville? The Maple Leafs’ goaltending depth will look a lot different next season, and time will tell if Marner has any influence on the outcome. His future in Toronto will be on the front burner should Boston finish the job, which unfortunately seems inevitable at this point.

Treliving has a lot on his plate this upcoming offseason. The long list includes potential extensions for Marner, Tavares, Domi and Tyler Bertuzzi and there will also be the task of finding a 1A starting goaltender. Let’s not forget five Maple Leafs’ defencemen currently don’t have a contract for next season. The cherry on top is the fact the coaching staff should be fully evaluated and it’s going to be fascinating to see which avenue Treliving wants to wander down in year two. Everything should be on the table. Despite the added pi-- and vinegar, the ingredients for success are still nowhere to be found.

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