We have a thing on this show, and it dates back to when Thomas Vanek was dealt by the Buffalo Sabers. It's a long, long time ago. The show has been on the air for a while. And the thing is that we talk about something that may or may not happen. And we go in-depth about what happens if it doesn't happen. And then immediately after the show is put out, the thing that we talked about for a good chunk of the episode happens. Last episode, we went in-depth on, Hey, what if the Leifs kept Timothée Lillegren? What would that look like? What are they really going to trade him for? Oli Matt only got a third. Oli Matt got a third, though. That's pretty good. Could the Leifs get that for Lillegren? He's only played one game this year. And we found out Timothée Lilligran was traded to the San Jose Sharks for a third and 25, a sixth and 26, which makes them easy to remember. Both of those picks way better than that Montreal 2026 second round pick. I'm just throwing that out there. That's not true. And Matt Benning as well, who's played over 440 games in the NHL.
Right shot defenseman, big guy, just had hip surgery, 30 years old. He's a guy that actually the Leaps were interested in five years ago to acquire as a depth piece at the deadline. Yeah.
Hip surgery will change things.
Sure. Sure. But I think he was thrown in there to help make the money work a little bit. They could bury the majority of his contract. I think he makes 1.25. They can bury 1.1 of that.
I think at this stage in both of their careers, I'd rather have Connor Timmins, but whatever. They mentioned yesterday yesterday that Benning could get flipped.
Yes, he might. Cj Show did mention that. Until he is flipped, he will marry number 55, last born by Mark Giardano.
Cj Show mentioned that he could get flipped? Yeah. Oh, I forgot the TSN part.
Yeah, exactly. Sorry.
That's the only place I heard it was on the CJ Show.
He could get flipped because the Lefs in this trade, they freed up some cap space if they sent Benning down, but they also didn't free up any roster spots because they took a player back, and now they've assigned Hawk and Pa and Duhard to conditioning stints, so they've delayed the return of those two gentlemen a little bit here, but eventually they're going to need a roster spot. So something's a foot.
And conditioning stints are two weeks. So we may not know about this until two weeks from now. That's right. So it could be a while.
They keep here.
I think what we should do on day 13 is go in-depth about it and then watch them.
Do you hear that metal clinking against concrete? That's them kicking the can down the road. I like that. Just another couple of weeks.
Yes, they're good at that.
In the immortal words of Lou Lamorello, If you have the time, use Sign it to seven years.
Yeah, sign it. If you have time, make sure that you get more time.
So much more time. So Timothée Lilligre. And it was interesting to hear Craig Berube talk about it because Tim's agent was interviewed. And Craig Barup, I said this, Looking back at training camp, I think guys just outplayed him a little bit. He's got the ability. He can skate and move the park. I wish him all the best. It just didn't work out here. That's the best way I can put it. And his agent spoke about it and said that it was stressful, that he was packing things up. But at the same time, he definitely... He probably wanted this, too. Well, his agent confirmed he wanted this. And you're still shaken by the phone call when you get traded, I think. I don't think that part's easy. But I think that this instantly puts him in top four, if not top two territory in San Jose. And if he can or if he can't, we'll know.
Yeah, I mean, I get sad every time someone who's been with the Leifs for a while.
Drafted, developed.
Drafted. I get sad. And this is a trade that I wanted to happen, and the Leifs got way more for him than I thought, obviously, based on last show. So why am I sad? I don't know.
I just feel like- I think you're sad at the lost opportunity for both sides.
Yes, that's 100% it for both sides. I feel there's regret to go around. I also love how classe he was about The agent did say one thing that I think we'll probably get to about the Lefs not exactly like liking him, which I thought was pretty funny. But he was honest. He didn't play well enough. They developed him, won a Calder Cup here, which meant something to me. I think a lot of this guy got set into motion when Rasmus Sandine got traded. I think that broke his heart a little bit. It's also heartbreaking that this contingent of the Swedish takeover that the Leifs had in their prospect pool for a while is over. It was Willy, it was Sandine, it was Envall, it was Lillagrin, it was Dimitri Timashow was part of that for a while as well. I'm trying to think of other guys I might have missed. I don't know. It made sad for the guy. But objectively, this is the right move for both teams. The Leaps were not going to use him. He lost his spot in camp. He did poorly. I did say something in the LFR that I rubbed some people the wrong way, but I'm going to stand by it.
But let me explain it.Controversial.
Steve.no..
Because I said he had two coaches and two GMs who he lost favor with. I stand by that. It's totally true. He had Dubas, and he had Keef, and he obviously fell out of favor with Keef. Or at very least, Keef didn't play him every single game. It was crazy to me that even up until last year, he hadn't played himself into a position where he's playing absolutely every night. Like, dude, you can't be getting taken out. At three million bucks, you definitely can't be getting taken out. And then Brad Treleving has had him for over a year. And then I said, Craig Berube. And people were like, well, jeez, that's a bit tough. No, you have the whatever it is, two, three weeks in camp and in spring, not spring training, sorry. In preseason to impress them and be like, here's why I should be here. He did the opposite of that. And it wasn't just me and it wasn't just Craig. Justin Borne, I remember, and maybe not everyone saw it because it was a preseason game, had a great intermission breakdown on Sportsnet, where he was just like, I'm not impressed with this player.
He's making bad decisions. You don't want him out there when you have a lead. You don't want him out there when you're behind. So what do you do here? So if Lilligran at 25 years old really develops into his own in San Jose, one, no one will be surprised. And two, I I really think it needs to be remembered that he's not in Toronto anymore for a reason.
Yeah, man. To support your point, Craig Berube has been here a little bit now. He's had the full training camp. Couple of months. He's had a couple of games. Nick Robertson did the exact opposite of Timothée Lilligran. There is an example of what you can do when given an opportunity. He hasn't been producing on the stat sheet, but what he did in preseason in training camp is he worked really hard. He points there. But the hard work and the mentality and just the skill he had he displayed during that period allowed him to gain favor with the coach. And now the coach trusts him to be there in big moments and to be on this team. It's earned him some rope. It's earned him Exactly. Lilligran had that opportunity time and time again with the least because he's been here for a while. With this head coach, he could have performed better in preseason. At the beginning of the season, he wasn't given that opportunity because he wasn't good then. That's his own in play. It's not on management that he didn't earn that spot.
The money factors in. I don't know if Timmins is miles better than Lilligren, but the problem is Timmins makes less than half.
Here's what Peter Wallen, who is Lilligren's agent, had to say that Steve alluded to. He said, He's always been on alert somehow. He's always needed to prove himself to the leaves. We always felt they didn't really, really like him. They liked him, but they didn't love him. I don't know. And so That's not the player you need.
Can you read the quote again?
He's always been on alert somehow. He's always needed to prove himself to the leaves. We always felt they didn't really like him. They liked him, but they didn't love him. I don't know.
This is the National Hockey League. Yeah.
Show us. You always need to prove yourself. Yeah.
What are you talking about? They spent a first-round pick on you. They brought you to North America immediately. You won a Calder Cup with them. Listen, I'm not going to sit here and pretend like over the years, we didn't go, Dude, what the hell? What does Lilligran got to do to be playing games over Justin Hall? And there were times where he a million % deserved to be playing games over Hall where he wasn't. And I can understand how that might screw with the person's confidence. And it's not like I don't ever have questions of confidence in myself, But the best athletes in the sport have a deeply ingrained belief in themselves that gets them over the top.
I'm never going to fault any agent for defending their team. No. Hell no. Saying something publicly that supports their player. Like, yeah, just pencil that in. They're going to do that. So I think that makes sense.
And that's just gentle a criticism of the leafs as I've ever heard an agent say. But maybe that's just because we hang out with Walsh.
And he's also being paid to say things like that. Yeah.
So, yeah, that's his job.
Let someone I know make $3 million and employ me. I will defend the hell out of them.
Are you kidding? Timothée Lilligren was drafted ahead of Josh Norris, Robert Thomas, Philip Heedle, Jake Ottinger, I mean, even Morgan Frost.
Here, give me a defenseman.
A defenseman?
Yeah, because all those guys- So he was drafted just after Uso Vallamacki, Eric Brandstrom, and Calfoot.
So the draft was going all defense at that point. So from 15 to 18.
I'm not going to lie, he worked out better than most of the names you just mentioned.
Pierre Olivier Joseph was drafted after him. Henry Yokey Haru in Chicago. He's okay. He's played a lot more games. Connor Timmins in first pick of the second round. Actually, that's hilarious. Nicholas Hague in Vegas, third pick. Oh, yeah. Nick Hague, yeah. Gustave Lindstrom.
But then how far down are you going now?
You're going far. But it's interesting, though, is that Mario Ferrero was picked 49th, which would have been great. I look at the leaves here and go, okay, he was supposed to go top five. That was a shock that he fell that far.
They made the right pick.
You had to try.
Considering they got William Neillander. I discovered this or reminded myself of this while shooting the Lilligran Trade video. The Leifs' first round picks go as follows, 2014, William Neillander, 2015, Mitch Marner, 2016, Austin Matthews, 2017, Timothée Lilligran. We're looking at this rebuild, and you might look at that and go, Oh, just get the best player, get the best forward. Dude, 2012 was Morgan Reilly. That was the last defenseman they picked first round. Then it was Freddie the Goat, Willy, Mitch, Austin, even like Korschkow was first pick of the second round in 2016.
It's all forward. It's because they were daft in the way they drafted for a while there. The Mark Hunter draughts were not very good. Despite what was propagated by one member of the media that people swallowed hook, line, and sinker, outside of the first rounds, Mark Hunter didn't have a great draft record here. Guys like who you just mentioned, Korschkopf.
What was the stat that went around? I think it was Josh Klokei. Out of the 2017 and '18 draughts, the only guy left is Pontus Humberg or something like that. It's really not good. But they needed a defenseman. And how long have they needed a right-handed defenseman? It's the 2017 draft. We just watched Eric Carlson, basically, Hercules, the sends to nearly the Stanley Cup final. And this kid falls into the leafs laps at 17. And we're like, well, you're not going to take him. You have to. He was the right pick. I think things cannot work out, and it still be the right decision at the time.
And I think that I think that the agents saying the least liked him, but they didn't love him. I think it was because in big moments, he made big mistakes. And at the beginning of last season, Steve took a lot of heat, and I think this is worth bringing up, for saying, We got to find out what Timothée Lilligren is. Are you a top four defenseman or are you waiver guy? And the reality is, we still don't know the answer to that. I don't think he's quite waiver guy.
I'm pretty confident. This is a great... I like the draft capital of the Leef Scott. This is frigging great for Lilligran's career. Yes. I'm confident he will not be waiver guy for at least a few years, even if things don't work out. Here, he was dangerously close to being Waver guy. If he didn't make three million bucks, he a million % would have been waiver guy. If he didn't shoot right-handed, he would have been waiver guy.
Yeah. Yeah.
Oh, well. It happens. I don't begrudge that. A lot of people like this guy. He had a lot of good numbers in sheltered third pair of minutes. And he was The king of giving you two weeks of this guy's going to be a God, Hockey, and then he'd get exposed. He was one of many prospects over the Matthews era who would tease you and tantalize you and sink more than swim more often than not over the long term.
A lot of defensemen like that. So the deal has happened League. Matt Benning is a leaf. The third and the six rounders are leaf picks. I would imagine that that third round becomes pretty valuable come trade deadline.
Yeah. In my video, I went over some of the trades that were made at last year's deadline. Vladimir Tarasenko Marco, who won a cup with the Panthers, was had for a third and a fourth. Carolina got Labushkin for a third. Tyler Toffoli went to the Jets for a second and a third.
Carolina got Labushkin for a third? I thought he was a leaf.
Not last year. Wait, or was it last year? No.
Wasn't Bush a leaf? Am I losing my mind?
What did you say, Steve?
I said Labushkin to the Hurricane.
Wasn't Labushkin a leaf?
Maybe I misread the thing that I saw. Anyway, Anyway, Jessie will look that up. Joel Edmondson was a third and a fifth. Right. I mean, yeah, is that going to get you a superstar at the deadline? No. But it's just something that helps you along the way.
Yeah, Labushkin never played for the Hurricans. Yeah, I thought that was weird. Oh, well. Yeah, he played for... He was on the Leaps last year. Yeah.
I know people are like, Can you take 20 seconds to Google things? But it's 20 seconds times 100. You don't realize how many things are said. I fucked up. I'm sorry.
That's Steve, you should live in that shape forever. I will. Yeah, I don't think it matters. The point is that when we've got-It was a third, though, wasn't it? Probably was. The point is, I think the least went into this year thinking, We hope that we don't have to make a move at the deadline for a depth defenseman. In fact, I think if they're going to make a move for anything, it's going to be a center. I think they're making a move for a center at some point. Unless Domi's looked pretty good on that third line. I think he's probably better suited at the wing, but I will take that. I would love for them to add to depth scoring at the deadline. Steve?
Yes.
Let's clarify and give you some credit. Because he was a hurricane. The Ducks acquired Kareil Sleps from the hurricanes for Labushkin, who then they flipped to Toronto for a sixth round pick. The way that Toronto got Elia Labushkinkin last February was in a three-way deal via the Carolina Hurricane, but no third was involved there.
Steve Dangle, Adam Wylde and Jesse Blake discuss the Toronto Maple leafs decision to trade defencemen Timothy Liljegren.