Now that the offseason has probably calmed down, at least until Kyle Dubas signs eight more guys in casual disregard of the SPC limit, we can try to evaluate it. For this purpose I have split my brain into parts. My fingers feel tingly!

The Kapanen Trade

Optimist: Say what you will about Kyle Dubas: the Kapanen trade is an unequivocal, hands-down robbery. In a year where it was so hard to move money that Tyler Johnson—who had 29 goals a season ago—cleared waivers, Dubas had the savvy to jump the market and push this trade on Jim Rutherford before Jim figured out it’s no longer 2004. Dubas got back a mid-first-rounder and a quality prospect in Filip Hallander, while unloading a player who for all his flash and speed, never quite took the final step fans hoped for.

Pessimist: Oh, sure. He got a good return.

Optimist: This feels like a trap.

Pessimist: No, really. He really has impressed me. He’s a great GM.

Optimist: It’s nice to hear y—

Pessimist: For a team in a rebuild. Who was the best player in that trade? Kasperi Kapanen. Do you know why the Pens acquired the best player in the trade? Because they’re a real contender that cares about winning now instead of accounting nerd fantasies of asset management. Kyle Dubas built a team, capped it out all to hell with overpayments, and had to start selling peripheral pieces of it before the team actually won a goddamn round. And we’re all just tickled pink about the trade return. This is like praising the receipts on a Going Out Of Business Sale. Teams that are seriously contending right now don’t generally applaud themselves for getting worse in the present tense.

Optimist: Except the team didn’t, when you take the whole offseason together. It’s never one move by itself, as good as this one obviously was. It was a reallocation. Kyle Dubas nailed the first piece, and, a little segue here—

The T.J. Brodie Signing

Optimist: —he nailed the second one too. T.J. Brodie is a top-pairing defenceman who plays the right side. He was the best option on the market if you didn’t want Toronto to liquidate half the roster trying to get Alex Pietrangelo. Dubas just gave Morgan Rielly the best partner he’s ever had in his life, and the chattering heads can’t seem to give him a scrap of credit for it.

Pessimist: Gee, I wonder why? Has Kyle Dubas ever acquired a—and I want to be clear I’m actually raising my hands from the keyboard to make air quotes here—”top-pairing defenceman” from the western conference? One who upon closer inspection turned out to be one of those machines that shoots tennis balls dressed in a jersey?

Optimist: Brodie is miles better than Tyson Barrie.

Pessimist: Sure looks like it after one of them plays a year for the Leafs and one of them doesn’t. Guess what they’ll look like after next season? T.J. Brodie is an eminently mediocre defenceman who has been carried to whatever fame he has by an actual goddamn Norris-winner in Mark Giordano, and we’ll all just assume that he’ll be a perfect fit with Morgan “Glass Cannon” Rielly. Hey, doesn’t anyone ever notice that every single pairing Rielly is on sucks defensively, and we always blame his partners? I’m sure this time will be different, though.

Optimist: If you can look at Brodie alongside Matt Hunwick, Ron Hainsey, Tyson Barrie, and Cody Ceci and not instantly conclude Brodie’s the best of the bunch, you’re being contrarian for the sake of it.

Pessimist: Well, yeah, that’s the premise of my character. But speaking of picking guys out of a lineup, most Leafs fans couldn’t have done that with T.J. Brodie two months ago. They spent an offseason swooning over Pietrangelo or Radko Gudas or Chris Tanev or Mackenzie Weegar, whoever the fuck that is, and suddenly when Brodie popped up on roster we acted like the ninth person we asked was who we really wanted to take to prom. For sure. He’s definitely not getting the Toronto glow. When has that ever led anyone to overrate a free agent?

Optimist: What else was Dubas supposed to do? As far as anyone can measure, Brodie was about the best RD on the market after Pietro. He signed to a fair deal. Yes, he’s looked good with good partners, would you rather he looked bad with good ones so you’re sure? You never get to buy perfect certainty and expecting Dubas to do so is asking him to buy in a market that doesn’t exist.

Pessimist: Sure. Actually, speaking of sure things, or lack thereof—

The Old Guard

Pessimist: lol remember when Kyle Dubas was supposed to be a progressive GM

Optimist: You think a bunch of bargain bin signings changes that?

Pessimist: Of course they do! The whole Dubas fanbase is gluing its eyelids shut in the face of reality. Wayne Simmonds, Joe Thornton, and Jason Spezza have a combined age of 213 and average 3.5 grandchildren apiece. After hearing what a young, fast, skilled team Toronto was supposed to be for years and years, we’ve realized, oops, we built the whole team wrong. You don’t go in an entirely different direction from how you’ve constructed the roster and get to pretend it just means everything was hunky-dory.

Optimist: Or, maybe it’s a way to cheaply add another element? Thornton and Spezza make, literally, the league minimum, and if they’re 85% what they were last year both of those deals will be incredible value. Yes, we paid a leadership premium of maybe $500,000 for Wayne Simmonds. Heavens forgive Dubas for making a modest bet on a guy recently removed from being a first-liner, who everyone loves, who comes from Toronto. If that’s the only overpay he makes the Leafs are the best-run team in the world.

Pessimist: It most definitely is not the only overpay he’s made, not by a long shot. But the fact is, if this weren’t a GM you liked, you’d say: this is him desperately trying to inject some savvy and leadership into a team that obviously lacks it.

Optimist: Thanks for your input, Mr. Cox.

Pessimist: Sure, sure, mittenstringers, old-school, boo. Do you think that it’s an accident that the Leafs grabbed these guys, plus Stanley Cup Champion (TM) Zach Bogosian? In your heart of hearts, when you’re not trying to win an argument on Twitter, when you watched the David Ayres game, when you watched this team flop around from January to March, when you watched them peter out like an empty water gun against Columbus, did you not think, maybe—just maybe—for all this talent and skill this team lacks something essential in the heart or spine or balls or whatever other part of the body you think has the organ for winning?

Optimist: Or, hear me out: it’s good to have good guys, who are also good players, on the team. Veterans on cheap contracts can give you value. You’re psychologizing this all to death when it can just be a nice, simple answer: Kyle Dubas saw some players he liked, so he went and signed them to good contracts.

Pessimist: He sure signed a lot of them!

The Jimmy Vesey Signing

Optimist: This is fine. You can’t get mad about—

The Travis Boyd Signing

Optimist: —a bunch of cheap players who—

The Alexei Barabanov Signing

Optimist: Stop it!

Pessimist: I could go on. Kyle Dubas, in the last gasp of a man who is clearly out of ideas, has settled for signing five too many players at every position and hoping somebody turns out to be alright. The team can’t afford to pay anyone worth a damn as long as the Big Four are making billions to lose in the first round, so Kyle Dubas has built three fourth lines and four third pairs and is hoping by some deranged mathematics that it’ll add up to the value of one of the players he can’t afford.

Optimist: What’s the risk? Of any of these? Except for Simmonds, all these contracts are 100% buriable. He’s created a competition and given the team more chances to find a diamond in the rough. Getting mad about guys who make under a million is really, clearly being upset for the sake of it, because the only downside is SPC space, which the Leafs have in abundance. Toronto has a pretty good chance of building depth that will pay out much more than it costs.

Pessimist: The problem is that the Leafs can’t afford to do anything but bargain hunt, and Toronto is going to talk itself into all of these players in quick succession. Hey, remember Pierre Engvall, whom everybody liked until it turned out his wrists are attached to bricks instead of any hand-like appendage? Now half of the fanbase is demoting him to the AHL and saying, well, it’s okay, it’s only a slight overpay for a guy who can’t make the press box...

Optimist: Again, these players are all cheaper than Engvall.

Pessimist: Because they’re bad! Oh, and let’s get this out of the way.

The Andreas Johnsson Trade

Pessimist: The Leafs, again a supposed contender, flipped an actual real player for Joey Anderson. Johnsson was one of their few long-shot bets that actually worked out, and they couldn’t afford to keep him more than a year on a deal they signed him to in 2019. And we’ll hear over and over again what a Tidy Piece Of Business the Anderson extension was, as if it matters at all to get a discount on an AHL player. You are patting Dubas on the back for playing penny-stakes poker while real, contending teams play chess.

Optimist: Good teams do this! They don’t marry their supporting players, they sign them and turn them over quickly to make sure they keep getting value. Otherwise you become the late-stage Blackhawks, who seem compelled by magic to fall in love with everyone who ever plays on their third line. Keep working, keep building, but the core of the team Kyle Dubas has signed is strong and will show it.

Pessimist: The definition of insanity—

Optimist: —is letting a five-game sample in a weird-ass qualifying round, where the opposing goalie stood on his head, dictate your team-building.

Pessimist: And we’re sure it’s not bothering Kyle Dubas. Nope, nothing to see here, just desperately signing some guys who were once real competitors because we’ve figured out our core players really aren’t. Anyway, let’s turn to the draft!

The Draft

Pessimist: A bunch of short, skillful wingers. We’re going for the record! It’ll be great when we have the best line in the Liiga in 2024. Too bad about the NHL.

Optimist: Bring back Mark Hunter! Draft more giant defencemen who can’t skate! That’ll fix it!

Pessimist: For the love of God: it’s not enough to be better than Lou Lamoriello and Mike Babcock and Mark Hunter! How long do these guys have to be gone before we make even the teeniest effort to evaluate this team on its own merits? Lou is gone (and has since won four playoff rounds, but it doesn’t count because we don’t like him.) Mark Hunter is gone. Mike Babcock is gone. And still we’re smirking in self-satisfaction about how Babcock would have scratched Joe Thornton on opening night or whatever. I don’t give a shit about being better than the ghost of a dead front office. When is this team going to win something in real life, instead of some pointless Internet argument you’re having with Darryl from Sudbury?

Optimist: Okay, evaluate Dubas’ drafting on his own merits. It’s way too early for most of it, but he’s obviously been successful. Sandin and Robertson have been huge draft hits and several other picks are progressing nicely. Yes, sure, most of them won’t make it, but what do you want? Drafts take time to bear fruit. That’s reality. Your impatience doesn’t make Dubas bad.

Pessimist: That’s the problem, though. How much patience is Dubas owed? How long does he get before we say he really does just have to win something? Because he owns it all, now. He has his coach and his three drafts worth of picks and his geriatric depth forwards. He owns this whole team and he owns how little it’s done yet. The Leafs are no longer a young team on the rise and they haven’t been paid like it in two years. If you’re happy with this team, you’re doing what Leaf fans have done for years: contenting yourself with mediocrity.

Optimist: This team has star players to go up against anyone in the NHL, a better defence than it’s had since Kaberle retired, and depth at every position. It has Sheldon Keefe in place with a camp to prepare.

Pessimist: Well, he’d have it, except for the apocalypse.

Optimist: Oh, right.

The State of the World

Pessimist: We’re doomed.

Optimist: Totally fucked.

How do you feel about the Leafs’ chances this season?