Photo Credit: San Jose Sharks v Vancouver Canucks / Derek Cain/GettyImages

It’s no secret that the Toronto Maple Leafs and management are in the hot seat this season. It has been nearly two decades since they last advanced to the second round of the playoffs, back in 2004. Since drafting Auston Mathews and signing John Tavares alongside plenty of other talented homegrown stars, Leafs fans’ expectations have not been met. For the past half-decade, they have been regular-season juggernauts but still have not made that jump and reached another level in the playoffs. That said, it isn’t a stretch to believe that their management hopes to bolster their lineup going into the playoffs. The best way to do that, at this point, will be through trades.

Before we hop into whom the Leafs should target and whom they may have to deal to get them, we need to look at their biggest needs. Despite defence being the talk for years, the most significant need for this deadline is a versatile middle-six depth forward. Another concern is goaltender health; Matt Murray and Ilya Sampsonov have missed enough time to draw some concern. It is definitely in the cards to think they may look into a veteran goalie with some playoff experience. And last but not least, if they can get a top-tier player at a good cost, they should at least pick up the phone, as any team would.

When working with trades, we need to look at assets. So who does Toronto have to throw around in trade talks?

The Leafs have some solid prospects and draft assets to work with. 

Starting with Nick Robertson, the 21-year-old, could have been much more valuable and possibly at the top of this list had it not been for his injury troubles this year. He has been amongst the top of the Leafs prospect pool since the team drafted him. With the big club this year, he has only played 15 games (2G/3A/5P). Despite the injuries, he is talented, and some teams may be willing to take him on his potential as a prospect.

2023 first-round pick, it is no secret that the Leafs are in win-now mode. So chances are they aren’t going to be particularly stingy with their first-round pick, which will be towards the bottom of the first round. However, I do not expect them to move another first-round pick for a rental. 

Next up, Fraser Minten; after being selected with the Leafs’ first available pick in last year's draft, the centreman has made huge strides forward this season in the WHL. He is well over a point a game this season with 47 points (25G/22A) in 40 games. Although the young stud has much potential, Dubas may be willing to send him out if it means saving a higher-touted prospect. 

Speaking of highly touted prospects, Topi Niemelä is amongst them for the Buds. The two-way Dman has put up a solid season in Europe. Personally, I believe it is very unlikely that he gets moved, however as the Leafs do not have much depth in terms of defensive prospects. 

Last but not least, from the prospects side of things is Leafs’ top prospect, Mathew Knies. The exciting thing about Knies is it may be possible for him to compete at the highest level as soon as this season. He remains unsigned as he plays in the NCAA. The big left winger is in the running for the Hobey Baker with 17 goals and 14 assists in 30 games this season. Likely, Dubas won't even consider moving him unless a high-end top 6 player is available. Even so, I don't see him being moved unless they can pull someone with term that is proven to be a high end forward at the NHL level.

Toronto also has 2 guys that are on the big league squad right now that are potential trade chips. First up is Pierre Engvall. The big Swedish winger has proven he can play a bottom-six NHL role and does it well. I wonder if Engvall is even on the table, but Dubas likely will not  hang up the phone if his name is mentioned. 

The next NHLer that might be on the block for Toronto is Alexander Kerfoot. Although he appears to be a solid locker-room guy and has not been bad this season, the forward might be on the way out. His offensive production has dropped, and he no longer appears to be worth the 3 and half million dollars he is getting, especially for the salary cap pinned Maple Leafs. 

Now that most of the trade chips, at least those with reasonable value, are out in the open. We can dive into the players that the Leafs may target.

10.  James Van Riemsdyk

The former fan favourite Maple Leaf is likely available at the deadline. This is a shot in the dark as a rental, but he would bring size and leadership to the group. The 33-year-old comes with a massive 7 million dollar cap hit, so it is unlikely that he is even an option.

Potential trade: 

Flyers receive: Nick Robertson, 2024 4th round pick.

Leafs receive: James Van Riemsdyk (50% retained)

9.  Max Domi 

For obvious reasons, Domi has been linked to Toronto since he was a prospect. The gritty forward has bounced around a little bit since entering the league. Chicago is selling this deadline, and there is no way Domi is off the table. He's a solid middle-six guy that plays tough and has a solid sense for the net. The good thing about Domi is he is going to bring a lot of the things that someone like Timo Meier will bring but not cost nearly as much. The difficult pill to swallow will be that he would likely be a rental. 

Potential trade:

Blackhawks receive: Pontus Holmberg, 2023 3rd round pick (Ottawa)

Leafs receive: Max Domi

8. Patrick Kane

Not a lot of ties to the Leafs outside of Auston Mathews. However, Kane would make a big addition to the top six. The biggest issue is going to be cost for value. Kane has noticeably declined from his prime, but its possible that a change of scenery could be just what he needs to find another gear. He would also slot into the lineup nicely.

Potential trade: 

Blackhawks receive:  2023 first-round pick, 2024 2nd round pick

Leafs Receive: Patrick Kane (50% retained)

7. Ryan O’Reilly

Like Kane, O’Reilly has not been the player he once was. However, he adds a more reasonable 7.5 million cap hit, still high for the Leafs but certainly more doable. He also brings the type of game they are likely hunting for. He has been a valuable asset for every team he has been a part of. The lingering injuries and cost are concerning.

Potential trade:

Blues receive: 2023 first-round pick, Nick Robertson

Leafs receive: Ryan O'Reilly

To add to this, the Leafs could potentially add Kerfoot to dump his salary.

6. Luke Schenn

Another former Leaf; however, Schenn, comes in on a league minimum contract and may only cost a 3rd or 4th round pick. A very reasonable cost to bolster the back end, which lacks in physicality. To me, if you can get him, you do it. 

Potential trade:

Canucks receive: 2023 third-round pick, 2023 6th-round pick

Leafs receive: Luke Schenn

5. Vladisov Gavrikov

This one is interesting; the left defenceman is relatively cheap but is bound to have interest from numerous trade deadline buyers. He likely will not remain in Columbus, and the Leafs should, at a minimum, make a call and test the waters.

Potential trade:

Bluejackets receive: Pontus Holmberg, 2023 3rd round pick (Ottawa)

Leafs receive: Vladisov Gavrikov

4. Ivan Barbashev 

The strong forward will add middle-six depth to any team, he's fairly talented and is a tough guy to play against. Coming in at under 3 million, he may be able to be resigned and fits the bill for what the Leafs need.

Potential trade:

Blues receive: 2024 2nd round pick, 2024 6th round pick

Leafs receive: Ivan Barbashav

3. Jake McCabe

He's a talented defenseman who has never played on a contending team. His underlying stats are impressive, given that he hasn't played with particularly good teams. He would make a great bottom-four dman and may even break out on a talented team. I wanted to stay away from dmen because I don't believe its at the top of the list of needs, but he comes with term and is healthy more than he's not.

Potential trade:

Blackhawks receive: 2024 2nd round pick, 2025 3rd round pick, 2025 7th round pick

Leafs receive: Jake McCabe (50% retained)

2. Jakob Chychrun

This one comes down to talent. He is a gifted two-way dman who is the best available trade target on the defensive side. The big issue for Chychrun is his availability. He has only ever played more than 60 games twice in his seven-year career. The cost would be high. However, he immediately plugs into the top D pairing and is under control for two more years.

Potential trade:

Coyotes receive: 2023 first-round pick, Fraser Minten, 2024 4th-round pick

Leafs receive: Jakob Chychrun

1. Timo Meier

By far, the best option for the Leafs adds forward depth by filling in on one of the top two lines, he is a restricted free agent, so his cost is going to be through the roof, and the leafs more than likely do not have the cap space to resign him, it's not impossible, but management needs to look at him as a rental. If they go in on Meier, Dubas will likely show fans that he is all-in to win this year. From what we are hearing, Toronto is close and has a frame for a deal done.

Potential trade:

Sharks receive: 2023 first-round pick, 2024 second-round pick, 2023 third-round pick (Ottawa), and a conditional 2024 fifth-round pick if Toronto signs Meier

Toronto receives: Timo Meier

All in all, there are many players to make Toronto better. Do they have the assets to get a team to bite, and are they willing to give those assets up? To me, the answer is yes, and I expect Toronto to make a big splash at the deadline.

-Brent Clemmer- Olde City Sports Network/The 6ixth Man

*Photo Credit- Steve Russell/Toronto Star via Getty Images