The Leafs are in an unfortunate position with Matthews and it's all because of Nathan MacKinnon

The Leafs are actually in fine position to be able to offer massive extensions to each of Auston Matthews, William Nylander and Mitch Marner, if they so choose. By electing to sign a series of short-term deals to create a supporting cast, Kyle Dubas has left himself a ton of room to make sure that he doesn't lose his star players because of a cap crunch.

The Leafs currently have just 4 contracts that run past the summer of 2024 (Mitch Marner, John Tavares, Morgan Rielly and Calle Jarnkrok), which is not a coincidence. The Leafs' management team and scouting staff also did their due diligence to ensure that they'll have plenty of entry-level talent coming in to fill in holes around the team's top players. A few of the names that we can expect to see step in starting in 2023 or 2024 include the likes of Nick Robertson, Matthew Knies, Roni Hirvonen, Topi Niemela, Nick Moldenhauer, Fraser Minten, Mikko Kokkonen, Ty Voit, Rodion Amirov and potentially one or two goaltenders (Hildeby, Peksa) who are all either on ELC's or coming out of ELC's and on inexpensive short-term deals. This will enable Kyle Dubas to remain flexible enough to offer even the largest of deals in order to retain his star players.

Another factor is the sizeable rise that is coming for the NHL's salary cap. Originally, the jump was not supposed to occur until the 2025-26 season, but now it appears as though we could see the cap begin to rise a year or two earlier, which could align with either the extension windows for Matthews and Nylander or Marner and Tavares.

With all of that said, even though the Leafs are positioned nicely for the extensions of Matthews, Marner and Nylander, there's still one factor that could come into play prior to the Matthews contract that could push his value far beyond what it may have otherwise been. It's the fact that Nathan MacKinnon is due an extension that will kick in next season. Rumour has it that he's gunning for the largest contract in NHL history.

For years, MacKinnon has been talking a big game about taking "less again" to ensure that the Avs remained well-positioned to compete for a Stanley Cup. Seldom to people actually acknowledge that MacKinnon never "took less" in the first place. When MacKinnon signed his last deal, he was coming off of a 53-point season and had exceeded the 60-point plateau just once in 4 NHL seasons. His $6.3M AAV was arguably not even fair value at the time his deal was signed. You could argue that the Avs were paying for his future. Boy did they ever hit on that bet. Needless to say, MacKinnon will not "take less again".

The largest contract currently belongs to Connor McDavid ($12.5M). MacKinnon will almost assuredly be gunning for a $13M or $14M AAV, which means that if the Leafs approach Matthews with any less than that, there's a good chance he's going to want to at least gauge the market elsewhere. The x-factor here, of course, is whether or not Matthews cares about being the highest paid player in the league. I can imagine that he would. Who wouldn't?

Could you see a scenario in which Auston Matthews becomes the $15 million dollar man in the summer of 2024? I certainly could. I hope it doesn't get that high, but I could certainly see it. We're not just talking about a superstar here. We're talking about a generational talent - at least from a goal scoring perspective - and since scoring goals is the hardest thing to do at the NHL level, I'd say he's well-positioned to be able to command that type of money. Especially if MacKinnon takes the Avs to the cleaners between now and next summer.