NHL Stanley Cup 2018-19 Betting Picks, Tips and Analysis

Adrian Dater

October 1st, 2018

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Quick Tips:

• Bet Pittsburgh Penguins to win Stanley Cup at +1800 with Karamba.
• Bet Winnipeg Jets to win Stanley Cup at +1150 with Karamba.
• Bet San Jose Sharks to win Stanley Cup at +1000 with Karamba.
• Bet Philadelphia Flyers to win Stanley Cup at +2500 with Karamba.

The National Hockey League is the Pandora's box of paradox for fans of NHL betting. Talk to people around pro sports, and the NHL often wins the day on the question of: “Which league has the most all-around parity?”

First-round playoff upsets aren’t just the exception, they’re the rule in hockey. An expansion team made it to the Stanley Cup Finals last spring, for crying out loud.

Yet, when you look at the list of Stanley Cup winners in the last 10 years, it comprises only five teams -- Chicago (three Cups), Pittsburgh (three), Los Angeles (two), Boston and Washington.

From 1995-2004, only five teams won the Cup (Detroit, with three), New Jersey (three), Colorado (two), Dallas and Tampa Bay.

An early look at the Karamba odds for the 2019 Stanley Cup favorite contains one big surprise as the favorite (Toronto Maple Leafs, at +800). If it happens, it’ll be Toronto’s first championship since 1967.

I’m here to tell you not to bet too much on that because, although the Leafs added a star scorer in the offseason, John Tavares, they still have to keep pucks out of their own net. Toronto’s defense and goaltending just aren’t there yet.

The Washington Capitals are the defending champs, but you get the feeling that was a one-and-done reign of power. The Lightning and Nashville Predators, teams rated right behind Toronto, are very good but not great.

These are my early suggestions as to where your money would be better allotted:

Best Bet to Win the 2019 Stanley Cup

Sidney Crosby badly wants another Cup. Without a doubt, the best play you can make right now is to bet the Pittsburgh Penguins (+1400 at Karamba). This isn’t a good bet. It’s a great bet.

Why? Because Crosby feels cheated out of what he thought was his destiny last spring. The Penguins of 2017 became the first team to win back-to-back Cups since Detroit in 1997 and ‘98, and it looked like a three-peat for Crosby was in store when they took a 3-2 Eastern Conference finals series lead on the Capitals.

Washington, however, overcame 45 years of playoff heartbreak to win the series, then the Final against the Vegas Golden Knights.

Crosby already will go down as one of the game’s all-time greatest players, but a fourth career Cup would separate him from all but a handful of players to have won it all that many times.

The Penguins have managed to keep their core of top talent still together in a salary cap era, and while guys like Crosby and Evgeni Malkin are both now getting older (each is 31), they are still young and healthy enough for a big run or two at a Cup.

Pittsburgh has a bunch of other guys who can score (Phil Kessel, Patrik Hornqvist, Jake Guentzel, Kris Letang), but perhaps the best reason for optimism is goalie Matt Murray. He had an up-and-down season in 2017-18, so he’ll be really motivated to prove he’s the same guy who led the Pens to back-to-back Cups before.

The whole theme of “Let’s Show the World We’re Still the Best” is why I like the Pens so much this season.

Top Canadian Pick to Win the 2019 Stanley Cup

Three other teams (Toronto, Nashville and Tampa Bay) are better favored to win it all than Winnipeg. Of those four teams, however, I believe the Jets (+1150) will prove the best of the bunch.

It’s hard to find any weakness to the Jets. They have a bunch of really excellent forwards (Patrik Laine, Mark Scheifele, Blake Wheeler, Nikolaj Ehlers), some premier defensemen (Dustin Byfuglien, Jacob Trouba, Josh Morrissey) and a top young goalie (Connor Helleybuyck).

The Jets beat 2017-18 President’s Trophy winner Nashville in the second round of the playoffs before being upset by Vegas in the Western Finals. They’re a young team that seems to have the grit and drive to not recede.

If that was their “learning how to win through losing” moment, then this could definitely be the first Canadian team since Montreal in 1993 to bring home Lord Stanley’s silver punchbowl. Bet the Jets at +1150 with Karamba.

San Jose a Tempting Stanley Cup Pick

Not only did San Jose general manager Doug Wilson snag the best player on the trade market this summer in high-flying offensive defenseman Erik Karlsson, he didn’t give up any blue-chip prospects in return to the Ottawa Senators.

The Sharks have probably had better rosters than this one in recent history, yet despite some Presidents Trophy seasons, they haven’t been able to win it all. With Karlsson added to a very good Sharks blue line that included Brent Burns and Marc-Edouard Vlasic, San Jose (at +1000 with Karamba) is worth some risk at the betting window.

The Sharks still have some worries with age. Center Joe Thornton is 39 and guys like forwards Joe Pavelski and Logan Couture are starting to get some miles on them. But Karlsson gives them, along with Burns, probably the best 1-2 punch on defense -- at both ends of the ice -- in the league.

Top Stanley Cup 2018-19 Sleeper Pick

The Philadelphia Flyers are the best sleeper pick. They probably need another good defenseman, and problems/Flyers goaltending have always gone together like peanut butter/jelly.

But at these odds (+2500 at Karamba), the Flyers make for an attractive sleeper pick to win it all for the first time since 1975.

The Flyers might have the deepest group of forwards now in the NHL, with free agent James van Riemsdyk added to a powerhouse that already included Claude Giroux, Jakub Voracek, Wayne Simmonds, Sean Couturier and Travis Konecny.

The Flyers will be one hell of a tough team to stop from scoring. Can they keep the puck out of the net enough to win an actual championship? That remains debatable, given the personnel on defense and goaltending. But this could be one year where the saying goes, “Offense won a championship.”

Take a flier on the Flyers at +2500 with Karamba.