Over the next few weeks, while the Stanley Cup is finishing up, I'm going to be writing about possible trades that might happen by or on draft day. Many will be suggesting trades on forums, but the perceived value of players is highly contested, even among GMs. A trade is actually more likely to happen when the value of a player is over-or-underestimated.
So discretion: I attempt to exact the value of a player, but in truth, nobody can exact the value of a player that fits the criteria of each of the 30 GMs in the NHL--too much discrepancy. What I'm essentially saying is: because trades are more likely to happen because of the discrepancy in the way two GMs value the same commodity, these trades are likely never to happen because they're too "even". If these Phil Kessel trades happen, it'll either be teetered to one side or the other, and we'll probably be face-palming.
Without further adieu:
Star right wing (top 5 in offense), probable two-way liability, entering his prime/arc (27), sub-par possession numbers, secured to a long contract, perhaps slightly overpaid, limited trade clause (he can list 8 teams he'll accept a trade to), character issues.
Toronto's goal with the trade: Getting rid of a stigma, getting good young players in return.
1. Florida -
Toronto gets: Huberdeau + 11th Overall
Florida gets: Kessel + 24th Overall
How good is Huberdeau, really? He's as much of an enigma as Phil Kessel is, but he's much earlier in his NHL career. But he's good. He led his team to a memorial cup; he won the calder trophy. What can Babcock do with Huberdeau? Quite a bit, I'm sure. Not only do they get Huberdeau, but at 11th, there's still some very good forwards available, including Kyle Connor, who might end up being a steal; even Barzal might still be available depending on what goes on between 6 and 10. If Toronto chose Dylan Strome or Mitch Marner, they could have potentially two really good centers in their system as well as an impact top six winger who's poised to get better.
What does Florida get? Florida is poised, now, to make the playoffs, and given Kessel's short stint in the playoffs, there is reason to believe that he might actually be pretty good in those situations. Kessel could benefit from a new start in a low profile market while Florida could make the playoffs next year, and not just make it, but compete in it. Florida ideally wants a player entering his arc since they might well be entering three-to-six really good years of dominance. They still get to draft a first and will be able to keep putting good players into their system in what's slated to be the deepest draft since 2003.
2. Arizona -
Toronto gets: Max Domi + 3rd overall
Arizona gets: Phil Kessel + 4th overall
This is an idiot trade. Toronto fans expect more. They'll want Arizona's 3rd overall pick without swapping theirs (they'll never get that... only Carolina's top 5 pick will be available for trade).
The pick swaps essentially makes sure that Toronto gets the pick of the two centers available. Maybe Arizona and Toronto are both feeling Dylan Strome. Maybe Dylan Strome will be a better "center" and Mitch Marner will be a better winger.
Either way: Leafs fans will wonder why trade an established player for someone who has pretty much no NHL experience. I'm not dumb. This would, however, be a gambit. Arizona has enough centers in their system and one of them might get very good. Kessel, who has little prestige left in Toronto, would be moved for Domi, who already has a lot of prestige in Toronto. Domi is also a heart and soul player who will thrive in a loud environment like Toronto, and Kessel is possibly the opposite of that. Domi is much younger and he'll be under Mike Babcock and Toronto will have the opportunity to draft Dylan Strome and have their center position set for the future without losing any excitement in the present, even if next season will be a learning curve.
Arizona probably truthfully doesn't need or want Kessel that badly, but their offense was horrible, and they'll instantly get a little bit more competitive. Arizona also has a pretty big prospect pool, so unlike Toronto, they're not exactly "restarting" their rebuild, but they notably have a shallow pool at right wing. If this trade actually did get bigger, Toronto fans wouldn't like what they'd additionally have to surrender (a defenseman).
Is this deal crazy? A dead hope? Well I guarantee you one thing, if Max Domi is going to play in Toronto, people are going to come to see him. The stigma vs. prestige swap alone is something that Shanahan and whoever he hires will be tempted to do.
3. Detroit -
Detroit gets: Phil Kessel, Matt Finn, (3rd)65th Overall
Toronto gets: Anthony Mantha, a decent prospect NOT named Larkin or Pulkkinen, Luke Glendening, (1st)19th Overall
This one would probably never ever happen. But I can tell you this, Holland would likely have a lot of interest in those two key players. I can see Toronto and Detroit being possible trade partners.
Holland says to everyone: "We're fine, we plan to be competitive every year". Truth is, they're not. I don't care whether they brought TB to seven games, the loss of Lidstrom and Rafalski really hurt and they haven't been significant in the playoffs since Lidstrom retired.
If Detroit wants to remain perennially competitive, they acquire an impact player rather than the 2nd liners coming up in their system. Holland has been a little too gun shy and needs to make a splash. Now that Babcock is in Toronto, he's going to know some of the players he'd like to bring in from the Detroit system, and Holland can generate a little bit more excitement in Detroit.
After all, whoever plays in Detroit simply becomes a better player. Could Kessel strive in Detroit? Yes, he could, and both teams could win from a trade like this.
I also imagine that Holland somehow structures the trade so that he can get Nylander, but that would require a lot more manoeuvring and talks would probably break down. Talks would break down between these two teams anyway.
4. St. Louis -
St Louis gets: Phil Kessel
Toronto gets: TJ Oshie
It's no secret that St. Louis is probably going to shuffle the deck at forward and Toronto wants to get rid of a stigma. RW for RW swap, Oshie has only two years left while St. Louis takes on Kessel's bulky salary still needing to sign superstar Tarasenko and two d-men.
Might need a little cap manoeuvring, but it can be done.
Truth is, I believe St. Louis will check to see what's going on with Malkin in Pittsburgh, since they're one of the only teams that can tempt the Penguins. If St. Louis finds nothing else, they might consider a move like this.
5. Calgary -
Calgary gets: Phil Kessel
Toronto gets: M. Backlund, 15th Overall, 52nd Overall, 53rd Overall
Calgary has plenty of cap space and they just made the 2nd round of the playoffs. They're beginning a new age. They apparently have a store of picks this year, so why not get rid of a few of them and acquire an all star winger to play on their second line?
Toronto, meanwhile, get a chance to further develop players at the start of their rebuild and pick up a third line center, giving them the option to move out other forwards without killing their team's competitiveness. You could argue that Toronto should get more, but that 15th Overall pick is actually a pretty good pick in this particular draft. There are a lot of 6-10 type forwards to be gotten between 6-19 of this particular draft year.
Toronto gets Phil Kessel under Mike Babcock
(blank) gets Phil Kessel under other coaches
Phil Kessel is no longer paid more than his coach, which means when Mike says jump, Phil says how high. A new dynamic in Toronto might have also traded away the old Phil Kessel, and might remove "some" of that old stigma. But if Phil's ultimately that angry under Babcock, he might waive his no-trade to go to other competitive markets.
Other notable possible destinations include: Nashville, Winnipeg, San Jose, and Carolina.