Betting the Stanley Cup Final

Justin Cuthbert breaks down his process for Stanley Cup and Conn Smythe futures betting before Game 1 between the Colorado Avalanche and Tampa Bay Lightning.

Video Transcript

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JUSTIN CUTHBERT: We are doing a "Yahoo Sports Hockey Podcast" short this afternoon. It's Justin Cuthbert, @JCCuthbert or @Cuthbets if you're looking for my gambling content, because that's what we're going to talk about now with a Stanley Cup Final betting preview. And of course, it's the Tampa Bay Lightning and the Colorado Avalanche in this year's Stanley Cup Final.

And if you've been following and tailing, then you're sitting pretty. This is going to be a little self-indulgent off the top. But I have to explain, excuse me, my process here in order to make smart bets for the Stanley Cup Final. And full transparency, I have futures bets on both teams. One is more lucrative than the other, and that's sort of reflected in the odds, but we'll get into all of that. But I kind of got to take you through from start to finish so that we sort understand exactly where we should be going here.

So Colorado opened the season at +600-ish, +650 maybe you could find it at, as the Stanley Cup favorites coming into the season. And I really wanted to find a way to bet them, but that seemed a little bit short to me, a little steep. I didn't really want to get involved at that price because I thought there might be an opportunity later on. That did present itself with the Avalanche kind of sputtering out of the gate. It wasn't too, too serious, but they didn't have the most dominant start. And I think the number jumped up to maybe 700 or something like that, and I jumped on it then.

However, as you probably know with all the commercials that you see, sports gambling became legal in Ontario where I am. So all the futures bets I had on certain sites got wiped away. So I lost that, had to rebuild. But thankfully, I had a lot that still survived and well, some that I wish didn't survive. But anyway, I had to look again for another way to get on the Avalanche.

And I was presented with this like boost opportunity at +400 when they were really like +350 or something. And I didn't love it, but I had the fear of missing out. I thought Colorado was the team to win this year. And I had been waiting for a price, and even that small little boost got me. But I jumped on at some point in April at +400.

And I also have the Lightning at +1,100 So they are the underdogs, and of course, that's reflected in what I have, but I got them I think after game 6 of the first round versus the Maple Leafs. So pretty happy with that number. Hoping, obviously, for financial reasons, that the Lightning do, in fact, win the Stanley Cup. But I think like, it's, oh, it's convenient, right, you have money on both of them.

Well, let me take you through everything that I did this year, because I think it's worth sort of talking about the building a portfolio aspect of sports betting, especially on futures bets. I've invested, full transparency, 9.5 units into the Stanley Cup market this season. I had three pre-season bets. One unit on the New York Islanders, awful.

A half a unit on the Florida Panthers, which was pretty good. And some of the reason why, in fact, I double, or went with Tampa Bay at +1,100 because I thought, OK, I'll have a decent number in the Conference Final and that team would be a favorite if the Lightning got past the Leafs, which I felt pretty confident in. Also had one unit on the Vegas Golden Knights, which was also an awful decision. So not a great start for me, although I did predict that the Panthers would be pretty good.

In season I added a unit on the St. Louis Blues at a really long price. I just thought, hey, this is one of the seven, eight teams that I think can win and the price did not reflect that. I think there were maybe like middle of the table and the odds were very good, so I jumped on that. And, of course, I got that boost, three units on Colorado weeks before the postseason began.

Now this process continues all the way up to it. So during round one, again, I got those two units on the Lightning down. And then during round three when it looked like the Rangers might have the Lightning, I put a unit on the Rangers as a break even failsafe, because I thought that they might go down and I definitely wanted this guaranteed profit, or at least guaranteed breakeven scenario in the Stanley Cup Final.

Now I'm not sure this is all positive expected value and all that stuff that you hear when receiving or giving gambling advice. But I do believe in building, as I mentioned, a futures portfolio, and investing in a market, and more importantly, rectifying mistakes. If I didn't rectify mistakes, if I didn't bet back into this market, I'd just be down two and 1/2 units I think it is.

I try over the course of the season to pick up value in all applicable markets. And now with the Avalanche and Lightning guaranteed to win, one of those two teams, I'm guaranteed to be up 5.5 units at least and as many as 12 and 1/2 units if the Lightning do, in fact, hoist the Stanley Cup.

Now more self-indulgence. Because the best example of building a position or buying or investing into a market that I have, at least right now, is the Conn Smythe Trophy. Now that process obviously began at the start of the postseason. I put down five 1/2 unit bets as a start, just to sort get the ball rolling. So half units on Johnny Gaudreau, because I thought Calgary had a decent chance to be in a Conference Final. Aleksander Barkov, because I believed in the Florida Panthers at the time. Andrei Vasilevskiy, Nathan MacKinnon, and Cale Makar.

So what I'm doing here, at least what I'm doing when I'm thinking about the Conn Smythe Trophy, I'm identifying teams that have a chance to win and the player who will likely receive the credit if those teams do win. And now three of those five are still applicable in the Stanley Cup Final. I had Vasilevskiy at +3,300. He's now down to +400. I had Nathan MacKinnon at +1,400, he's down to +210. And Cale Makar at +1,800. He is the favorite right now to win the Conn Smythe Trophy at +200.

So seeing these prices drop is an awesome thing, obviously, that's what you want to see. But this is a one outcome event. So you can't cash all of these bets or take advantage of the fact that all these prices have dropped. But if you do build that futures portfolio, if you build that position properly, you'll be in great shape, and I am in great shape holding on to those three tickets. And I did add, because that's what you do. You continue to mine value over time, even if you liked what you saw out of round one with Makar, MacKinnon and Vasilevskiy.

So after round one I put a half unit on Jacob Slavin, because I thought Carolina had a decent chance to go far. That proved to be an awful decision. But it was +2,700. It was worth sort of a little hedge. I put a half unit on Jordan Binnington at a large price. I think it was +5,500, because if anyone, if Colorado was going to trip up, it was St. Louis, who was next up for them. And that was a really long shot odd. And a chance, I thought St. Louis had to go to the Stanley Cup Final and Binnington was going to play that key role.

I put another unit on Andre Vasilevskiy at +2,900 at the time, and another unit on Cale Makar at +650. Then after round two, I put another unit on Nathan MacKinnon because he was just a megastar in that series versus St. Louis. And another unit on Andrei Vasilevskiy at +850. Again, same sort of thing happened for me in round 3.

As a hedge, I grabbed Igor Shesterkin, one unit, because the Rangers were threatening. And if anyone was going to get credit for that, it was going to be Shesterkin. Shesterkin was going to win the Conn Smythe Trophy if the Rangers won the Stanley Cup. So I thought at a long shot odd and an ability to basically cover off any loss, that was a decent hedging opportunity, especially with how much I had on Andrei Vasilevskiy.

So all told, 8.5 units so far into the Conn Smythe Trophy market. And a Vasilevskiy wins, we stand to improve that by four or five times I think and close to double that or maybe even more with Makar or MacKinnon winning, which is great being up 8.5 units minimum unless there's one sneaky underdog that we'll talk about a little later. That is a great upshot if you're gambling on this market.

We do have that one blind spot though. I'll get into it now; why not. And that's the emergence of Nikita Kucherov, who inexplicably in my mind, has shorter odds to win the Conn Smythe Trophy compared to Andrei Vasilevskiy. And this is something I disagree with wholeheartedly. Not because I stand to profit majorly if Vasilevskiy wins. I just don't think there's an argument for Kucherov beyond like a lifetime achievement award sort of thing.

Like just looking at what they've done through three rounds, I would give Vasilevskiy the edge, even though Kucherov as the leading scorer for the Tampa Bay Lightning. But more important than that I think, I think the situation in the Stanley Cup Final sets up perfectly for Vasilevskiy to shine. But if in some way Kucherov gets the edge, let's say there's a couple of hat trick, he plays out of his mind, he's one of the main reasons why Tampa lifts the cup, I might have to identify that at some point.

Like if he has a major performance, I might have to bail out. I might have to throw something on Kucherov during the Stanley Cup Final to ensure some profits, even when the Lightning just winning the Stanley Cup will cover all that off. I just want to make sure I don't waste away the fact that I have such great odds on Vasilevskiy and the ability to double up, at least if Colorado wins the Stanley Cup.

Anyway, I think it was important to preface the betting opportunities that the series presents with that context, because it's going to impact what I'm going to do here, what I'm planning to do. And part of the reason why it's important, is because I like the Tampa Bay Lightning. And again, I stand to profit more so from the Lightning winning than the Avalanche winning.

There were some +170s hanging around early on the Lightning. For the team that has the superior netminder, regardless of who goes in for Carolina, or Colorado. They should get the bigger boost from the injury list with Brayden Point being closer, at least it seems than Nazem Kadri, and probably more capable when it comes down to it.

And they also have the history of not just winning the Stanley Cup the last two seasons, but solving opposing teams is really their forte. So if I didn't have money on each and more to gain with a Tampa victory, I would have played the Lightning to win the series at +170 immediately. And I still would advocate for it at +155, where it stands currently, because I believe this is closer to a coin flip series.

I would also look at the series spread. And the Lightning +1 and 1/2 games, so to either win the series or lose in 7, is at -150. That's what's being offered on the Lightning right now. And again, it makes no sense for me to lay the juice on an outcome like that in my position. It just, I don't, if we're going to go to positive EV, I don't think that's positive expected value.

But I would be all over it probably if it was more in the -120 range, where it's more, or closer to an even money scenario. But I do think that's a decent way to play it if you're just looking to jump in now and bet on the Stanley Cup Final without really anything else going on. But in my position, I think it's putting in a little less to win a little bit more, as to not like carve into the profits I've already secured.

So where I'm going to play the series or what I'm looking at right now is the Lightning in 6 at +575 and the Lightning to win in 7 at +575 as well. Both of those are very interesting to me, because I think if the Lightning are going to win, those are the most likely scenarios. And of course, +575, even if you make both bets, very nice profit.

Colorado to win game 1 and lose the series also caught my eye at +475, but I think I'd rather consider betting the Lightning to win the series if they lose game one rather than playing that. Because I don't really know what game 1 is going to look like. The price probably wouldn't be +475 on the Lightning if they do lose game 1.

But like this rest versus rust thing is tricky, right, because we saw with Tampa the rest did not really benefit them at all. And Colorado has had nine days off here between these, the Western Conference Final and the Stanley Cup Final here. But they also play at altitude. And I don't know how that's going to affect the Lightning coming in or how this series is going to look like immediately. I mean, the Lightning really are a team that gets a read on opponent first and then figures out a way to beat them.

They've lost two of their three game 1s so far. So I just don't want to mess with that. And I think it would be wiser to just wait and see if you want to put a series bet on the Lightning, because there's a good chance they lose game 1. And there's also a good chance that Colorado has a lot of it early on I think, and the Lightning winning a little bit later, and that's why identified Lightning in 6 and Lightning in 7 as potential bets for me.

Other things to consider. Series total games over 5.5 is -180. The problem with it is going to be real sweaty of Colorado wins the first two, because then they only need to win one in Tampa Bay to have that opportunity to close out in 5 on the road. And then you've spent a lot to make very little at the -180, even though I think it going over 5, getting to a 6th game is very, very likely.

But the series total over 6.5, so going 7 games +210 is interesting. Of course, you need a game 6 not just to happen, but for the result of it to go your way in order to win. But I think it does set up for a hedge out opportunity with that + money. You've secured your profit. If you're confident in the series going to game 6, you can find a way for that to work for you.

As for the Conn Smythe Trophy, I think it's hard to play either Cale Makar or Nathan MacKinnon at +200, +210, +220 each. It's a coin flip series, it's a coin flip between them. So I think right there, the value is sucked out. I go back to Andrei Vasilevskiy, who's the value play, at least in my eyes, at +400. I cannot imagine voters wouldn't want to vote for him given the opportunity it provides to tell a legacy story. This is a goaltender threatening to be the best at his position of all time, if not the most clutch and critical piece to a modern day dynasty. The narrative is there.

But more importantly, the numbers back up that narrative, which sort of makes it a slam dunk, at least for me I think. I guess the voters, as I mentioned, could go Kucherov, who has the more points than anyone in the last three previous post seasons combined by like a mile. He has been fantastic. He has been someone who's maybe, could be considered at least a little bit hard done by.

But its legacy over sympathy for me all day. So if you don't have a position on the Conn Smythe, I would be looking at Andrei Vasilevskiy +400. It was +450 when it opened, I believe, and yesterday or when it reopened after the Stanley Cup Final was set, I believe that was to start the week. But again, as I mentioned, I have to consider the possibility of Kucherov winning and making a bet to cover my ass.

The other name, and I really think it's a four-horse race, but Steven Stamkos maybe is on the fringe of that discussion. If he was lights out, there's a chance I guess, because the narrative is also there. The personal redemption arc is there. But he would have to be spectacular I think to wrest it away from either Vasilevskiy or Kucherov in the event that the Lightning win.

So to tie up my plans here with either outcome creating profit, if you've been following me, then you're in the same position, and the payouts reflecting the current odds where you get a little bit more to bet on the Lightning, a lot more, actually, I'm going to hold off until at least game 1 and see if it's worth betting on the Lightning in series.

But for now, I'm going to scoop up some longer shot markers just to hold for later on, low risk to set up either hedging or cherry on top opportunities. So the Lightning in 6 and 7 at +575 each. I'm going to call those official plays. And hopefully, if you're following along and you're invested in the Conn Smythe Trophy market, it's Vasilevskiy and not Kucherov if the Lightning cash either at 6 or 7. It's Vasi who leads the Lightning in terms of importance in those late series elimination opportunities.

We're just catching up to the betting thing like everybody else, because of course, it was legalized this year. But hopefully, we're going to infiltrate it more and more into our coverage. Obviously, we have here in the Stanley Cup Final, but as we set up next year, we're going to do a lot more of this and figure out ways to try and make some money, specifically in the NHL futures market, because that's my favorite way to bet on sports.

We will have the Stanley Cup Final on lock here at Yahoo Sports. We got "Zone Time," we got the "Yahoo Sports Hockey Podcast," we've got in the mentions making its return with Omar. It's all great stuff over the next two weeks with a dream Stanley Cup Final. I hope you follow along with us. And I hope you make some money and cash some of those Conn Smythe futures.

You can follow me @JCCuthbert and @Cuthbets. We'll have more and more betting and NHL content to go. We'll take a little break in the summer, but we'll be back and it's going to be a great Stanley Cup Final. So Thanks again for listening and thanks for tuning in this entire season. It's been a great year and it's been capped off with a fantastic Stanley Cup Final.