13 Toronto-area free agents that the Leafs could eventually go after

This morning, Mike Babcock had another one of his usual pre-game media scrums, and slipped in a little nugget about how he’d like the team’s identity and success to help with the Leafs’ ability to pursue local talent.

This was in reference to the fact that the Calgary Flames have eight Toronto-area players in the lineup tonight; historically, that’s always appeared to be an issue, though it could just be that the league has a lot of Toronto-grown talent and that the Leafs have been bad for a while.

Certainly, I’m not of the “you need Toronto boys to succeed”, Don Cherry-esque camp, though I’ll happily admit that the idea that Mitch Marner screams down the wing and probably flashes back to what Phil Kessel or Gary Roberts or Sergei Berezin would do in that situation is a lot of fun. Plus, having that edge to lure those big names when they’re available would be great; Toronto was closer in the Steven Stamkos sweepstakes than any 30th place team regularly would be, and while he ultimately decided to stay in Tampa Bay, the goal should absolutely be to find ways to be a bit better armed for those situations if they come up again.

Now that the league has been made aware that the Leafs have what’s likely to be the brightest young core in the hockey world, and now that the team looks like it could go from the draft lottery to the playoff party, there’s a bit more ammo to work with. With that all in mind, here are some of the highest profile free agents from the somewhat near the Toronto area that are coming up in the next few years.

Thornton’s probably the more interesting ones of this bunch, both in the sense that he’s the most immediately available and the sense that he’s the one they could perhaps get silliest with from a cap perspective. An unrestricted free agent this summer, the 37-year-old has seen better days but remains on a point pace in the high 50’s and continues to be one of the game’s better two-way forwards. San Jose came within two games of the Stanley Cup last year but fell to the Penguins, leaving Thornton still craving his first ring.

Toronto has an obscene amount of money to work with this summer, given the entry level contracts that they’re working with, and while they may not offer him a multi-year deal like other teams, the could probably offer him multi-year money for a single season. Even if it costs $11 million, how insane would it be to go from years of Grabovski vs. Bozak debates to having Joe Thornton as the Leafs’ third or fourth line centre during a cup run? This one depends on how much gas he thinks the Sharks have left in the tank; I wouldn’t put it as a guarantee by any means, but if he gets to June, the possibility is certainly greater than zero.

Nash didn’t quite pan out to be the player we all hoped and dreamed he would be, but the 6’4 former first overall pick still produces like a top liner, isn’t a complete tire fire from a possession perspective, and his gains in that regard come from offence, which the Leafs likely wouldn’t mind. He’ll be 34 years old in 2018 though, so your hope is that he’s looking for one of those Eric Staal-esque redemption deals.

If Toronto were to have their eyes on him, it would be in a depth scoring role and to help on the penalty kill, an area where the Rangers have used him with some success in stretches.

This is “the big one” for a lot of people. Some to the point that when Stamkos rumours flared up last year, a lot of people said they’d rather wait. It’s hard to blame them, too; John Tavares is on my “Tier of Three” as far of favourite active players go, and he’s one of the best players on the planet. Having him and Auston Matthews one line after another would instantly make the Leafs’ Lines 1+2 the most cerebrally talented top six in all of hockey, with Tavares being the “veteran” closest to what Matthews is as a player.

Tavares is also fiercely loyal, though, and while the Islanders have been the definition of hot garbage this year, they’ve been very good to him over the years. While he’s from Toronto, and while the Leafs have effectively meddled to try to get him on multiple occasions, I simply don’t know if he cares enough about being here that it’ll stop him from staying in Brooklyn as long as the team even remotely turns it around in the next year or so. I’d love to be wrong, and I’d encourage the Leafs to even throw a long-term deal at him given the skillset that the then-27-year-old has, but I’m still not sure about this one.

I’m only including Neal here because I know somebody will bring him up. I don’t really want James Neal. He’s due for a big raise, he’ll still be 30 so he’ll probably cash in on term, and I don’t want the Leafs’ kids to learn how to knee players in the head. Nashville Neal isn’t the same as Pittsburgh Neal was anyway, so unless he’s begging to be here, he’s an afterthought.

It’s amazing how awesome Spezza still is at this hockey thing, even though he isn’t talked about as much. The 33-year-old plays very high event hockey, and he’s still good for 55-60 points a year. He’ll be 36 when his deal with Dallas expires, so who knows how he’s playing then but he’d be a fun cheap fourth liner to use remaining buffer space on at that point. 

2019 is a huge year for local-ish UFA’s. Doughty is by far the biggest, but I think he falls under the same category as Tavares. He’d be a tremendous get that would undeniably solidify this team at every position it needs to be solidified in, but the Kings don’t seem to quite be going anywhere yet and he grew up wanting to play for them. My bet is he signs an extension there.

To the prior point, I could see Couture joining Doughty down the highway in Los Angeles before I could see him coming home. I do think he’ll have a new team at the end of his deal, with Thornton, Vlasic, Pavelski… basically every big mid-to-vet aged core player other than Brent Burns coming up for extension with no clear contending window in sight.

That might be for the best, too; he’s going to get paid very well, and I can’t imagine him being more than support by the time he gets here. Not a slight to him; this is just a team that has a lot of young weapons.

I really like Matt Duchene; he’s a very very good offensive player, skates like the wind, and while his underlying metrics are bad, the Avalanche are a catastrophic tire fire. I think they’ll be the ones deciding his future; like Doughty with the Kings, he grew up an Avalanche fan from afar, and if they don’t trade him but find a way to figure their future out instead, he’ll likely re-up.

Seguin has matured a fair bit over the years, and has become a legitimate top line talent that contributes in pretty much every facet the Dallas Stars need him too, even playing right wing when they’ve needed him to move away from centre. 

This is a signing I’d probably make purely out of spite for all the “Kessel trade!!” stuff we had to hear for years, though I think he’s going to look to get paid. His $5.75 million cap hit on his six-year deal is absolute larceny for the services he provides, and either Dallas or another team is going to pay him through the nose when he turns 27 and approaches or hits the open market.

Skinner went from “he might be better than we all thought” to “he might be a bust” to “oh, he’s actually probably what we thought in just a few NHL seasons. The 24-year-old is a 55-65 point threat on the left wing on an annual basis, is a spectacular skater, and is offensively inclined in his shot impact. I do expect the Hurricanes to be one of the better teams in a few years, though, so he’ll probably stay here.

Pietrangelo has been rather good for the Blues for a very long time, and I think he’ll get bored of being on a good enough team within the next three years. I don’t think he fits the Toronto model, though; he’s not a particularly high-pace player. This will also be his “big contract”, so it’ll likely come from a team that’s desperately lacking any semblance of a defence core (so, at that point, probably still the Buffalo Sabres).

Tanev is a player that, if the Leafs decided to go into the direction of having one “shutdown” pair and/or line over the course of their window, I’d rather them trade for rather than waiting for him to hit free agency. He’ll be due for a gigantic raise at that point, seeing as he has one of the most cap friendly contracts in the league right now relative to his performance.

Dream big. Dream huge. McDavid is the best player of our generation and has a very real chance of being one of the best players of all time. He is the evolution of the game realized in one player – lightning fast, super skilled, and acutely aware of what’s doing on. Having him and Matthews together would make even the Crosby-Malkin duo in Pittsburgh feel like a little less of a big deal. Not just that, but unlike most of the people here who are just connected to the Leafs by geography, he’s very well known for being a Leafs fan growing up; during the garbage years when local kids stopped caring, no less. For goodness sake, his self-comparable before the draft was Tyler Bozak

There’s a lot of work that needs to be done if you’re swinging for Connor, though. You need to hope the Oilers don’t do too well. Then his next contract will be key; he needs to keep it short. Four years is the goal, but will the Oilers give him that easily? Unless he’s dead-set on coming here, will he even specifically ask for it? I think you hope for it, and if by some crazy chance he makes it to restricted free agency, you come in almost immediately with a very convincing four-year offer-sheet. That way, either the Oilers have to match it and you’ve both made their cap situation rough and moved him to UFA as soon as possible, or they walk away and, while you’re giving up four first rounders and making it so you have to squeeze the budget for a bit, you have Connor McDavid.

Of course, he could sign an eight-year extension in July, nerfing this day dream once and for all, or until 2026, whichever comes first.

To be honest, a lot of them are likely just noise. Many will go back to the teams that they play for, or they’ll go to teams that will give them more money or term. The Leafs are going to be in a situation where they’ll have a stacked core and are looking for sweeteners, so unless any of these guys need a redemption year or are an absolute perfect solution to a hole that the Leafs can afford to fill at that exact moment, I wouldn’t bet my life savings on any of these moves.

I suppose the ones I’d focus on the most are Thornton as the months progress, Tavares if he gets to opening night next year without a deal, and McDavid if you like daydreaming about winning a bunch of cups in this extended window instead of “just” snapping the drought.

But the more important thing is the context of these conversations. It’s not longer “local GTA native will save us, he clearly wants to”. We’re now talking about these top players as support, and we’re talking about them coming here more because they want to win than because we assume they have some sort of obligation. The players are sweeteners to Toronto’s build, and Toronto is a sweetener to the players’ hopes. That’s a very different and, quite honestly, exciting context.

As an aside, the other great thing about a successful Toronto team is that it could have an impact on future GTA-area players, in the sense that more of our youth will likely be motivated to play again, and many of them will grow up with Marner and McDavid mindsets rather than being mostly indifferent like Tavares or having other favourite teams like Duchene and Doughty. The trickle-down from that will probably reap more long-term rewards than this list, if we’re being honest about the whole thing.