Toronto Maple Leafs forward Auston Matthews John E. Sokolowski-USA TODAY Sports

As the Toronto Maple Leafs patiently wait on an Auston Matthews extension, the passing of time brings with it an ever-growing concern that issues will arise in getting this deal done. 

Already passed the date where the Leafs hold real leverage (he now possesses a full no-movement clause), Matthews can realistically walk away from the team at the end of the season in free agency, should he so choose. The Maple Leafs aren’t likely to trade him even if he opts not to sign, but questions about whether that’s the right plan of action are fair.

Poised to be the highest-paid player in the NHL, the Toronto Maple Leafs could go way off the board and realistically let Matthews leave and go in another direction completely. The questions then become, is the club better to allocate his money in other ways and can the organization land two players where the sum of their parts is greater than what Matthews can offer alone?

What Players Could the Maple Leafs Pursue?

One quick look at a site like CapFriendly, and it’s easy to see that there’s a solid group of pending unrestricted free agents that will be looking for a home during the 2024 off-season. If the assumption is that Matthews is going to garner a $13.5 million commitment per season for at least four or five seasons, operating under the guidelines of that criteria, there are options worth considering.

Among the top names and centers that will potentially be available are Elias Lindholm (Calgary Flames), Steven Stamkos (Tampa Bay Lightning), Mark Scheifele (Winnipeg Jets), Alexander Wennberg (Seattle Kraken), Mikael Backlund (Calgary Flames), and Chandler Stephenson (Vegas Golden Knights), among others. All would come in at a cost much less than Matthews, with Lindholm and Scheifele likely the closest, but probably not exceeding the $10 million per season mark.

It’s fair to argue none of these players are of the caliber of Matthews, but that’s not exactly what we’re looking for. The goal here is to find someone who can offer a solid percentage of Matthew’s production at a lesser cost. It’s Part B (or the additional asset) that becomes important as this conversation unfolds.

For example, Lindholm offered 82 and 64 points in the last two seasons, respectively. Matthews offered 106 and 85. Is Matthews’ average of 95 points over the past two seasons worth paying another $4 million per season when you can get Lindholm’s average of 73 points for roughly 70% of the cost? Some will say no and some will say yes, but the other asset added becomes important.

Toronto Could Then Grab Another Solid Playe

Assuming the Maple Leafs could sign one of these players (which they likely could), that would leave Toronto around $3M-$4.5M to land another top-six forward or reliable defenseman. Much of what would go into that decision would be based on the team’s window to win. Would GM Brad Treliving want to target someone on a shorter-term deal that helps immediately and brings experience? Or, would this be someone on a longer-term contract that can grow with the team as it redefines itself?

Someone like Sam Reinhart out of Florida would be an interesting option but may be too expensive. Jake DeBrusk may be ready to leave Boston based on how well the Bruins perform. He’s more affordable. Brady Skjei will be a 30-year-old defenseman finishing up his contract with Carolina and looking for a solid deal. Or, if the Maple Leafs want to shift focus from forward to defense, maybe they make a significant offer to Devon Toews who may be out of the range the Colorado Avalanche can afford to pay.

If looking at it from a combination point of view, does a mix of Toews and DeBrusk work out to be more helpful to the Maple Leafs than Matthews alone? What about a pairing of Skjei and Wennberg? You can mix and match all you want, but it’s more about making the argument that two solid players, each with unique skills to offer provide more value than just one.

The Team Could Choose To Invest In William Nylander

The key to remember here is that the Maple Leafs also have an option internally that they could look at. The consensus feeling is that William Nylander is more likely to be moved than Matthews because there isn’t enough money to go around for everyone. What if Toronto chose to prioritize Nylander at around $9.5 million per season and then added another $4 million player to compliment him as Matthews departs?

Nylander might excel when given more responsibility, and if the Leafs can pick up another player to compliment the group, the loss of Matthews will still be felt, but possibly lessened.

None of this is ideal. The optimal thing would be for Toronto and Matthews to get this deal done and for the two sides to move forward together. But, if there’s any doubt in Toronto that thinks things will work out that way, it might be wise for Treliving and company to start browsing the market to see if a combination of free agents might be worth targeting.

More must-reads:

TODAY'S BEST
Pacers' Pascal Siakam leads team to Game 6 win vs. Knicks
Watch: Matt Duchene's 2OT winner sends Stars to conference final
Scottie Scheffler shoots improbable 66 after warming up for PGA Championship in a jail cell
Report: Tua Tagovailoa away from Dolphins amid contract chatter
Nuggets star has worrying comment about latest injury
Paul Skenes makes incredible Wrigley Field history in second-career MLB start
Giants rookie CF to undergo season-ending labrum surgery
Yankees' Juan Soto reacts to Hal Steinbrenner contract talk
Late goal sends Panthers to Eastern Conference Finals
Ex-teammate of Shohei Ohtani placed bets with same illegal bookmaker as interpreter 
Former Rams first-round pick retires from NFL after 11 seasons
Insider provides major injury update on Celtics' Kristaps Porzingis
Watch: Bruins strike first in Game 6 with incredible backhand goal
Dodgers make series of moves involving notable players
Hurricanes not expected to re-sign defenseman, center
Maple Leafs tab former Stanley Cup winner as new head coach
NFL insider expands on competition between Steelers QBs Russell Wilson, Justin Fields
NFL sets outrageous prices for Eagles-Packers Brazil game
Broncos 'very unlikely' to bring back former NFL interceptions leader
Greg Olsen offers broadcasting advice to Tom Brady