Toronto Maple Leafs

Toronto Maple Leafs forward William Nylander could be set to become the team's second-highest paid player with his next contract.

The Maple Leafs could offer Nylander an eight-year, $11.25 AAV extension this season, according to TSN's Darren Dreger.

Dreger believes that an eight-year extension could increase to as high as $11.5 million per year.

"I don't doubt for a second that it is top priority for the Maple Leafs to get this guy extended," Dreger said Wednesday on TSN 1050. "It's getting to the place where I think he can appreciate as a star player, he's likely earned it."

Nylander is currently set to become an unrestricted free agent following this season.

He has 51 points (19 goals, 32 assists) through 36 games, putting him on pace for the first 100-point campaign of his career.

This explosive pace, following two straight 80-point seasons and a 40-goal campaign in 2022-23, could mean 27-year-old Nylander would fetch an even bigger price on the open market than he could earn in Toronto.

That is something Dreger believes the Leafs will try to avoid, especially given the uncertainty surrounding the team's other upcoming contract negotiations. Both John Tavares and Mitch Marner, who are set to become free agents following the 2024-25 campaign, will be looking for extensions of their own next season.

"If you're William Nylander, why would you expect or negotiate for less, or what is team-friendly?" Dreger asked. "And conversely, the team is sitting there and going, 'Okay, well, we're not sure what we're doing with Marner going forward... can we really allow William Nylander to play hardball and go to free agency? If he's willing to look for $13 million out there— and it might be out there— are we going to lose him for nothing?'"

"I just don't think the organization can do that."

The extension projected by Dreger would leave only Auston Matthews ($13.25 million AAV) with a larger cap hit than Nylander next season.

A deal north of $11 million per year would exceed what the Leafs are paying for Tavares ($11 million AAV) and Marner ($10.9 million AAV) in 2024-25.

Even with the cap set to increase by more than $4 million next season, that means Toronto could spend over half of their total cap space on their top four players.

That might be worth it if the Leafs can hang onto a player currently producing at a pace on par with the Edmonton Oilers' Connor McDavid.

Toronto Maple Leafs star Auston Matthews is off to a hot start this season, and one lucky fan received his game-used stick following Saturday's 7-4 win over the Minnesota Wild.

After the game, Matthews, who is of Mexican heritage, noticed a young fan in the Scotiabank Arena stands holding a sign that read, "Mexican roots. Leafs. Go Auston!" He made it a point to get him his stick after the win:

Matthews scored his second straight hat trick of the 2023-24 season during Saturday's game. He opened the year with three goals in a win over the Montreal Canadiens on Wednesday.

The Maple Leafs selected Matthews first overall in the 2016 draft and he has emerged as one of the best players in the NHL. He is a two-time All-Star, two-time Rocket Richard winner and the 2021-22 Hart Trophy winner as the league's MVP.

Matthews became the first player of Mexican heritage to ever win the Hart Trophy.

The 26-year-old has appeared in 483 games for Toronto across eight seasons, notching 305 goals and 243 assists for 548 points.

Matthews, who was born in San Ramon, California, grew up in Scottsdale, Arizona. His mother, Ema Matthews, is originally from Hermosillo, Mexico.

Given his Mexican roots, the Maple Leafs could be among the top candidates to appear in a future NHL Global Series game in Mexico City.

NHL chief content officer Steve Mayer said on ESPN's The Drop podcast this week (h/t ESPN's Greg Wyshynski) that the league is considering Mexico City as a future location for international matchups.

Matthews said in 2021 that it would be "awesome to literally play a hockey game in Mexico and just see what happens."

Matthews and the Maple Leafs will be back in action against the Chicago Blackhawks on Monday.

Toronto Maple Leafs head coach Sheldon Keefe has been signed to a multi-year contract extension, the franchise announced Wednesday.

The extension is for two years, according to Sportsnet's Elliotte Friedman.

Maple Leafs general manager Brad Treliving said in the announcement:

Since I've joined the Maple Leafs, I've been very impressed with Sheldon. He has shown great leadership skills with his staff and our players, and has a clear vision for this team and where it needs to get to. Sheldon has established himself as one of the top coaches in the league and I look forward to working alongside him as we head into the upcoming season.

Keefe added:

Coaching this team has been a great privilege, and I'm truly excited at the opportunity to continue building towards our ultimate goal. I'm thankful for the support from MLSE and its ownership along with Brendan Shanahan and Brad Treliving, who I've really enjoyed getting to know and work with this off-season. We have so many great players and people within our organization that I'm grateful to work with, and together our commitment to team success remains steadfast.

Keefe joined the Maple Leafs in June 2015 as head coach of their American Hockey League affiliate Toronto Marlies, leading the team to a Calder Cup championship in 2018 before being hired as head coach of the NHL club in November 2019.

The 42-year-old has coached the Maple Leafs to a 166-71-30 record in his four seasons and also led the team to single-season franchise records in wins (54) and points (115) during the 2021-22 campaign.

Toronto has a .622 winning percentage under Keefe, which ranks behind only the Boston Bruins, Colorado Avalanche and Carolina Hurricanes in that span.

However, the Maple Leafs are 13-17 in the postseason under Keefe despite boasting a highly talented roster that includes Austin Matthews, Mitchell Marner, John Tavares and William Nylander.

Toronto made it out of the first round last season for the first time since the 2003-04 season, but it suffered a disappointing second-round loss to the Florida Panthers in five games.

Given Keefe's extension, the Maple Leafs must feel he can be the guy to get them over the hump and into the Stanley Cup Finals for the first time since the 1966-67 season when they won their last title.

Six-time All-Star Auston Matthews has agreed to a contract extension with the Toronto Maple Leafs.

The team announced the extension is for four years.

Matthews sent a message to fans on social media after the deal was announced:

Per Elliotte Friedman of Sportsnet and NHL Network, the total value of Matthews' new four-year deal is $53 million ($13.25 million per season).

The extension makes Matthews the league's highest-paid player by average annual salary:

Matthews was entering the final season of his five-year, $58.2 million contract that was signed in February 2019. He is set to earn $750,000 in base salary during the 2023-24 campaign, but he will also make $7.2 million through his signing bonus.

This extension keeps Matthews under contract to the Maple Leafs through 2027-28, but it also allows him to potentially hit free agency at the age of 30.

The Maple Leafs selected Matthews No. 1 overall in the 2016 NHL draft. He signed a three-year entry level contract with the team and appeared in all 82 games as a rookie.

Matthews became the first Toronto player to win the Calder Trophy as the league's top rookie since Brit Selby in 1965-66. He finished his debut season with 40 goals and 29 assists.

The California native has since established himself as one of the best offensive players in the NHL. He led the league in goals scored in back-to-back seasons in 2020-21 (41) and 2021-22 (60).

Matthews set a career-high with 106 points during the 2021-22 season. He had his fourth consecutive 40-goal season in 2022-23.

Toronto has made the playoffs in each of Matthews' first seven seasons, but the team hasn't advanced beyond the second round. The franchise's two best seasons by regular-season point totals have come in each of the past two seasons (115 in 2021-22 and 111 in 2022-23).

Former Toronto Maple Leafs first-round pick Rodion Amirov has died at the age of 21.

Amirov's agent, Dan Milstein, announced his death Monday and said he was diagnosed with a brain tumor "two years ago." The Maple Leafs released a statement saying they are "devastated by this tragic loss."

"From the moment he received the news, he refused to speak in the negative, determined to enjoy every day, facing it with the same positive attitude he showed during his hockey career," Milstein said. "We will always remember his courage, his desire, his will, his smile, all of the great things about him."

A native of Russia, Amirov starred for Salavat Yulaev Ufa in the KHL before Toronto selected him 15th overall in the 2020 NHL draft. His nine goals and 13 points ranked third among under-20 skaters in the KHL during the 2020-21 season, according to the Maple Leafs.

The Maple Leafs announced on April 15, 2021, that they signed Amirov to a three-year, entry-level contract and he would be moving to Canada to join the team's Toronto Marlies AHL affiliate. Less than a year later, Toronto general manager Kyle Dubas announced on Feb. 23, 2022, that the left wing prospect was diagnosed with cancer. Later that year, Amirov returned home to Russia to continue undergoing treatment.

"We'd like to thank his doctors, who took great care of him. We'd like to thank the Toronto Maple Leafs and his KHL - Salavat Yulayev Ufa team. Both did everything possible to help in any way, do whatever was necessary for Rodion and the Amirov family," Milstein added. "And we'd like to thank hockey fans all over the world who sent notes of encouragement and best wishes over the past two years. They meant so much to the Amirov family."

Compounding the salary cap issues facing the Toronto Maple Leafs, and their ongoing negotiations with Auston Matthews for a new deal is the lack of an extension for William Nylander.

TSN's Bryan Hayes reported that the Leafs appear content to "play chicken" with Nylander and his people, willing to let things go into the season, knowing full well that he can walk next offseason and the team would receive nothing in return.

It is a risky power play for the Leafs and one that may backfire.

The Leafs are in the middle of a Stanley Cup push and the window to win their first since 1967 is open. That is why they went out this offseason and signed Ryan Reaves, Max Domi, and Tyler Bertuzzi to free-agent deals. It is why the team is trying to get its best player, Matthews, under contract.

Make no mistake about it, though, Nylander is an important piece in the Stanley Cup puzzle.

He is coming off the two most prolific seasons of his career, including his most goals (40), assists (47) and total points (87). He added 10 more points off four goals and six assists in the postseason. On top of that, he was available, appearing in all 82 regular season games and bringing stability to the team.

This is not an overpaid, overvalued veteran player.

The team is reportedly content to take a position of power with a player who does not need the Leafs nearly as much as Toronto needs him to make its dream of hoisting the Cup a reality.

Yes, the team is in a tricky financial position given cap limitations and currently has its hands full re-signing the centerpiece of the organization, but imagine the frustration Matthews would feel if he commits to a team for the long-term with the idea of winning, then watches a key player in that walk away because the Maple Leafs decided to play hardball.

There are young players and free agents who could fill the void but Nylander has been a staple of the Leafs since he was drafted in 2014, has gotten measurably better in every area, and is arguably in the prime of his career.

Hayes' report did state that the Leafs want Nylander back and understand the importance of getting a deal done, so the franchise is not wholly ignorant to the position it finds itself in. Still, "playing chicken" is a game that the front office of one of sports' most historic franchises does not have to participate in.

Let Nylander know he is important, ensure him a deal will get done, and go about working toward escaping the second round of the playoffs.

Even better if the pen can be put to paper before the season, thus avoiding the distraction that comes from relentless questions about the future of the star player.

The Athletic's Pierre LeBrun reported that the Toronto Maple Leafs and forward William Nylander are far apart on an extension for the 27-year-old star.

Despite the current status quo of the negotiations, it would remain in the best interest of both the team and the player to come to an agreement on a new deal.

Above all else, Nylander is a star player who accounted for 40 goals, 47 assists and his best shooting percentage since the 2015-16 season. Five of those goals were game winners, reflecting his ability to deliver in big spots.

It would be incredibly difficult to find a replacement that can account for all that

Letting him walk as an unrestricted free agent would be a massive mistake for the Leafs' front office and should be considered out of the question.

A trade in hopes of recouping something for a player of his quality would typically be the alternative option but as LeBrun points out, that is difficult in the current landscape.

"As talented a player as Nylander is, what the Leafs have found out this week is that his trade market isn't nearly as robust as we might have predicted. There's just no cap room out there, and any team trading for Nylander would want him extended."

There is also the issue of the impending Auston Matthews deal, which will be equally as difficult to complete given the team is already over the cap.

Despite the cap issues, the Matthews deal and potential trade options, LeBrun believes the team will continue working to find a way to keep Nylander in Toronto. "There appears to be a sizeable gap. But my sense is the Leafs will just keep hammering away at it hoping to find a path to an extension."

And it should.

Whether it succeeds or not remains to be seen but absent a trade partner that is willing to pay up to extend Nylander (and is not on his list of 10 no-trade candidates), the team must work on presenting the forward a deal that is both team-friendly but also reflective of the contributions of the player.

Nylander is part of one of the most formidable offenses in the NHL. While the defense is suspect, the offense is and always has been Toronto's guiding force. It is what sets the Leafs apart from other teams in a loaded Eastern Conference and is what the organization has built around.

Losing Nylander by trade or through free agency would leave a hole that, without an immediate replacement, would severely hamper the Leafs' ability to hoist the Stanley Cup that has eluded the Original Six franchise since 1967.

Toronto either gets the deal done before the end of next season (and, preferably, way before then) or watches a key player in its pursuit of hockey's ultimate prize walk away with nothing to show for it, neither in the trophy case nor the spot he once occupied on the roster.

After helping the Boston Bruins win the most regular-season games in NHL history last year, Tyler Bertuzzi is headed to the rival Toronto Maple Leafs.

Bertuzzi signed a one-year contract with Toronto, the team announced Sunday. The winger will make $5.5 million, TSN's Chris Johnston reported, marking the highest annual salary of his career.

Bertuzzi was a successful trade deadline acquisition for the Presidents' Trophy-winning Bruins last season, scoring four goals and 12 assists in 21 games on the team's third line. Prior to his stint in Boston, the winger recorded 88 goals and 114 assists in 305 games with the Detroit Red Wings, who drafted him in 2013.

Bertuzzi, who recorded his first career 30-goal season in 2021-22, was held to eight in 50 games last campaign thanks to brutal injury luck.

The winger made just nine appearances for Detroit between October and January 2022. After hurting his hand on a blocked shot in the second game of the season, Bertuzzi missed nine contests. He returned, played seven games, and then suffered another hand injury, this one requiring surgery and sidelining him for months.

When healthy, Bertuzzi spent most of his time in Detroit on the Red Wings' top line, flanking Dylan Larkin with Lucas Raymond on the other wing. The trio was offensively successful enough to help earn Larkin an All-Star nomination, but at times got exposed for their defensive weaknesses.

Once traded to a deeper Bruins roster, Bertuzzi thrived in his newly sheltered position, heating up offensively as he settled into his new third-line role. Including the first round of the playoffs, Bertuzzi recorded 17 points (six goals, 11 assists) in his last 11 games of the campaign.

Toronto's deal for Bertuzzi is a vote of confidence that the 28-year-old will be able to continue producing at a similarly blistering pace in 2023-24. He is now the team's highest-paid player behind Auston Matthews, John Tavares, Mitch Marner, William Nylander and defenseman Morgan Rielly.

Having dedicated over $40 million, or over 48 percent of the salary cap, to the team's top four forwards, the Maple Leafs have limited wiggle room left under the cap. They will hope Bertuzzi puts up another 30-goal season, or close to it, as the team looks to fill out the rest of the roster with cheaper contracts.

The Toronto Maple Leafs may look to end their 56-year Stanley Cup drought by acquiring San Jose Sharks defenseman and 2023 Norris Trophy winner Erik Karlsson in a trade, per The Athletic's Pierre LeBrun.

It will not be easy for the Leafs to make the deal as the team attempts to extend stars, Auston Matthews and William Nylander, especially given Karlsson has four years remaining on an $11.5 million deal.

The team enters the offseason with an estimated $6,743,551 in cap space, per Spotrac.

Still, the Stanley Cup hopefuls need to make the deal if even remotely possible.

Sharks brass are willing to eat a portion of the deal to make the move, but by no means does that suggest the team will not be looking for fair compensation for the superstar player.

"He's not someone I'm just looking to give away," Sharks general manager Mike Grier told reporters in a Zoom call.

"But for people to think we're going to eat 50 percent of his contract and all this type of stuff, it's probably not going to happen," he continued. "...Erik's a special player who is on the path of being a Hall of Fame player."

The Leafs have also expressed interest in a trio of Calgary Flames defenders (Noah Hanifin, Chris Tanev and Nikita Zadorov) and given general manager Brad Treliving's friendship with new Flames GM Craig Conroy, it would not be surprising at all to see the team acquire one of those young, intriguing players instead.

If that were to occur, the team would be settling rather than jumping at the opportunity to acquire a player that would make the team demonstrably better.

The Leafs are an offensive-minded team, especially with Matthews at the forefront. They can score with anyone but have lacked production on the defensive side of the ice.

Karlsson would provide that.

This past season, he accounted for 101 points from the blue line, with career highs in points and assists. His shooting percentage of 12 was also the best in his 14-year NHL run.

There are, and should be, concerns about his health and ability to play an entire season. This past season was the first time he appeared in 82 games since the 2015-16 season.

Even so, the question then becomes whether the Leafs are willing to miss out on an opportunity to acquire a player that will enhance their ability to win the title that has eluded them for five decades on the chance that Karlsson will be injured and miss time.

"I'm the best when you need to be the best. But if I don't have the chance to get to the place where you need to play the big games, then I might as well not do it. I could go through 82 games a year and be good, but I want to play when matters," the Norris Trophy player told reporters Sunday when discussing his desire to play for a contending team.

The Leafs have oftentimes, and deservedly so, been criticized for not playing up to the moment. If the team can make something work, while still keeping the cap space necessary to assure the extensions of Matthews and Nylander, they would be foolish to settle for any lesser player.