Maple Leafs Could Break Up Core 4 With a Toffoli Deal

Although most of the speculation about the Toronto Maple Leafs’ contract extensions revolves around Auston Matthews, the need to resolve William Nylander’s contract situation is looming not far behind. While there has been less discussion about it, it remains important to the team. As Maple Leafs’ fans know, his current contract is a six-year deal worth $45 million.

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Nylander’s contract will expire after the 2023-24 season. As a result, so as not to lose him for nothing in free agency, the Maple Leafs probably want to re-sign him to an extension this offseason.

Nylander Deserves a Raise

Nylander is coming off an outstanding season. He recorded career-high point numbers with 40 goals and 47 assists (for 87 points) during the 2022-23 regular season. He also played well throughout the playoffs, with four goals and 10 points in 11 games. Given these strong performances and the fact that he was signed to what turned out to be a team-friendly $6,962,366 cap hit, he will be seeking a raise in his next deal.

Related: Revisiting the Brent Burns Trade

It was reported that Nylander wanted to stay in Toronto and asked former general manager (GM) Kyle Dubas not to sign him and then quickly trade him after he signed his first big contract with the team. But does he still want to remain with the team; and, does he want to sign another team-friendly deal?

Complicating all these contract negotiations is that new Maple Leafs’ GM Brad Treliving has been burned during previous experiences dealing with key players approaching free agency in his time with the Calgary Flames. Specifically, Johnny Gaudreau left the Flames for the Columbus Blue Jackets in free agency, and Matthew Tkachuk requested a trade out of town. It’s likely Treliving will remember that and be less trusting this time around.

Johnny Gaudreau Calgary Flames
Johnny Gaudreau, formerly of the Calgary Flames (Amy Irvin / The Hockey Writers)

Although there’s every reason to believe that the Maple Leafs will do their best to re-sign Nylander to an extension, what if contract negotiations seem to be going badly? That’s where Tyler Toffoli comes into play. If contract extension talks do not progress well this next week, by July 1 the team could explore the possibility of trading Nylander.

Would the Calgary Flames Be a Suitor, and If So For Whom?

Specifically, would Treliving trade Nylander to the Flames for Toffoli and potentially another player? A possible trade scenario would move Nylander to Calgary for Toffoli and potentially Nikita Zadorov. Zadorov is a huge defenseman who’d add physicality and would provide much-needed toughness on the Maple Leafs’ blue line. He could also bolster the team’s penalty kill. 

Related: 7 Cool Things About Jarome Iginla: Calgary Flames Hall of Famer

Another trade scenario, and one that was explored a bit by my THW colleague Spencer Lazary (although his post didn’t mention Nylander), was the addition of Flames’ goalie Dan Vladar. Vladar would potentially be an option for the Maple Leafs with Joseph Woll. Although they have the rights to Ilya Samsonov, who knows what his asking price might be? 

Ilya Samsonov Toronto Maple Leafs
Ilya Samsonov, Toronto Maple Leafs (Amy Irvin / The Hockey Writers)

The 25-year-old Czech goalie Vladar currently has two more years on his contract, with an average annual value of $2.2 million. That should be considerably cheaper than Samsonov’s salary demand.

Toffoli Brings a Different Game than Nylander

Nylander is known for his offensive prowess, but Toffoli was the Flames’ leading offensive player last season. However, he brings a more well-rounded game, particularly on the defensive side. His experience and solid two-way play could enhance the Maple Leafs’ overall game. 

The Flames could find the trade enticing for a couple of reasons. First, acquiring him would bring a significant offensive boost to the roster. Nylander, a Calgary native, also has a personal connection to the city. His father, Michael, played for the Flames between 1993 and 1999. 

Related: William Nylander’s Success Means Unclear Future in Toronto

Second, the Flames would have the opportunity to part ways with Toffoli, who doesn’t intend to re-sign with them anyway. Trading for Nylander could inject excitement into the Flames’ lineup, giving them hope for the season ahead.

How the Maple Leafs Might Win

Few Maple Leafs fans would like to see Nylander leave – and, I’m a huge fan. However, there are benefits for the Maple Leafs. The team would still have a reliable scorer in Toffoli to fill the void left by Nylander. His offensive production has been consistent throughout his career, and he has the ability to score consistently. 

William Nylander Toronto Maple Leafs
William Nylander, Toronto Maple Leafs (Amy Irvin / The Hockey Writers)

Toffoli has Stanley Cup-winning experience with the Los Angeles Kings. That might prove valuable in the Maple Leafs’ quest for a long playoff run. In addition, his lower salary cap hit compared to Nylander’s contract would potentially free up valuable cap space for the Maple Leafs to address other roster needs or make future moves.

The Bottom Line

The possibility of trading Nylander for Toffoli and potentially Zadorov or Vladar remains speculative. However, it’s intriguing to explore the potential benefits such a trade could bring for both the Flames and the Maple Leafs. 

Related: 7 Cool Things About Carey Price

The defensive contributions and experience Toffoli would offer the Maple Leafs could help address some of the team’s weaknesses. At the same time, Nylander’s offensive prowess could inject excitement and scoring power into the Flames’ lineup. 

Tyler Toffoli Calgary Flames
Tyler Toffoli, Calgary Flames (Jess Starr/The Hockey Writers)

Additionally, given so many Maple Leafs’ fans desire that the Core Four be broken up, this trade should strike their fancy. It would also allow new GM Treliving to make a big trade without really changing much on the team. That, in itself, could be a positive for many frustrated Maple Leafs’ fans. 

Who knows if such a trade could be pulled off? However, it isn’t out of the realm of possibility. It could, in fact, become a win-win for both teams.