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The Degenerate’s Guide To Gambling: Stanley Cup Playoffs

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stanley cup playoffs

What a Sunday in Augusta. Even with some of the top guys like Spieth and Rickie falling off late, Sergio Garcia and Justin Rose gave us some dramatic theatre to watch on the back nine. As you all know, Sergio made a charge after back-to-back bogeys on ten and eleven to force a playoff. His eagle putt on 15 was easily the moment of the tournament for me, followed closely behind by Kuchar’s ace on 16. While there wasn’t great golf all weekend thanks to the high winds on Thursday and Friday and the world number one not even teeing off, it ended with a great storyline, which is great for the game. In an attempt to not be overshadowed, your league MVP Russell Westbrook went for 50-16-10, which was topped off by a game winner from 30 feet. The triple-double average is now a sure thing, but until he’s given the MVP by Adam Silver, I’m going to keep putting this up.

On to this week. The NBA finishes its regular season slate, the best playoffs in all of sports start on Wednesday in the NHL, and there’s a free UFC card Saturday night on Fox. Here’s my weekly attempt to help you guys from getting knee-capped by your bookie.

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Eastern Conference

This side of the bracket is so one-sided that it’s really not fair. The three top teams in the Metropolitan division are three of the four best teams in the NHL. With the ridiculous seeding format the NHL uses to promote division rivalries, we get stuck with this nonsense where two of them will be eliminated before the conference finals. On the Metro side, you have the Presidents’ Trophy winning Capitals taking on Toronto. The Caps have too much all over the ice for a young Leafs team to contend with, and I expect this to be done within four or five games. Caps are -210 at home, and the odds should be closer to even for games three and four in Toronto. Then you have the Penguins and the Blue Jackets, the biggest first round travesty. With two of the best teams in the league, this feels like a conference finals matchup. I’m taking Columbus in this one, and that’s with full disclosure that I’m a huge Jackets fan, and will be in the building for game three on Sunday. The Jackets will ride the league’s best goaltender, Sergei Bobrovsky, and get just enough offense to take down the Pens in six or seven games. The Jackets are +135 on the road, and should be around -140 when in Columbus.

On the Atlantic side, we have the Rangers taking on the top seed Montreal Canadiens and the Bruins taking on the Senators. The Bruins/Senators series could be super interesting. Boston really hasn’t played great hockey all year with the talent they have, and took advantage of a weaker Atlantic division to get into the Cup playoff. With guys like Pastrnak, Marchand, and Tuukka Rask, I expect them to take out the Senators with talent alone. The Sens play a slow, methodical style of hockey, and can wear on you, which is why I expect another six or seven game series. Boston is coming in a lower seed, but is -125 on the road in Ottawa. Montreal and New York is going to be a head-turner in my opinion. Montreal is the top seed on this side, and have done so with terrible offense and great goaltending from Carey Price. New York has been up and down all year, but still came up with 102 points in a ridiculous Metropolitan division. I’ll take the Wild Card Rangers to take out the Canadiens in a series where Henrik Lundqvist returns to form in goal. The Rangers are +120 in Montreal, and should be a slight favorite in games three and four when they come home to the Garden.

Picks: Washington Capitals, Columbus Blue Jackets, Boston Bruins, New York Rangers

Western Conference

In a year that the Western Conference has shown to be the weaker conference, I believe that they have the league’s best team. Though Washington has the Presidents’ Trophy for the second year in a row, the Chicago Blackhawks are the team to beat going into the playoffs. The ‘Hawks get the Nashville Predators in the first round, which is a less than ideal draw. With talent upfront like Forsberg and Johansen, P.K. Subban on defense, and Rinne in goal, the talent is there for the first round upset. Chicago gets the -170 odds at home, and then should be about even when in Nashville. Chicago will win in five or six games, so I would ride the guys in the red sweaters.

Staying on the Central Division side, you have the Minnesota Wild and the St. Louis Blues. Minnesota hit a cold streak toward the end of the season where they came back down to earth from where they were around the all-star break. I expect them to get by Tarasenko and co. in the first round, but it will not be an easy matchup. Minnesota is a -150 favorite at home, and could be a slight road dog in St. Louis, but expect them to win in six or seven to set up a great Minnesota/Chicago second round matchup.

The Pacific division has gone through twists and turns over the second half of the season. San Jose seemingly had a stranglehold on the division, but a few of their top guys have been nursing injuries to close out the season. Couple that with Edmonton and Anaheim getting hot, and you now have them playing on the road in Edmonton in the first round. Look for Connor McDavid to put on a show in his first playoff appearance. The kid, in only his second year, is arguably the best player in hockey. Oilers fans have been waiting to get back to the postseason for a while, and I expect the team to jump on the opportunity they have in front of them. Edmonton is another team with -140 odds at home, probably about even on the road, so if you ride them, you should end up in the red. Calgary and Anaheim is a fun first round matchup as well, with the other Alberta team making it into the postseason after a long layoff. As much as I want an all-Alberta second round between the Oilers and the Flames, I have to pick the streaking Ducks. Between the combination of Perry and Getzlaf, along with their young goalie in John Gibson, the Ducks should have no trouble pulling this out in five or six. Gaudreau and Tkachuk make for a great young nucleus in Calgary, but they’re just not ready. Anaheim is -160 at home; ride the Ducks.

Picks: Chicago Blackhawks, Minnesota Wild, Anaheim Ducks, Edmonton Oilers


After last week’s entertaining yet controversy-ridden UFC 210 in Buffalo, we get a free fight card this week on FOX. The two majors fights worth note are Demetrious Johnson (-800) taking on Wilson Reis for the Flyweight Title, and a de facto title eliminator between Jacaré Souza (-225) and Robert Whittaker. Let me start off by saying that Johnson is the absolute safest bet in all of sports at this point. He’s going to break the record for title defenses in a row in the near future, and he is the perfect fighter. He hits you, often finishes you, and never gets touched. With that comes insane odds and low payouts, with him sitting at -800. I’m hoping that after this fight, he takes a super fight with one of the big three at 135 lbs (Garbrandt/Dillashaw/Cruz).

The middleweight bout between Souza and Whittaker is puzzling to me as far as the odds go. Souza is a former Strikeforce champ who can and has competed against and beat the who’s who at 185 lbs, whereas Whittaker is a blossoming star from Australia whose best win is vs. Derek Brunson. I was expecting something in the realm of -400 for Jacaré, so -225 is a steal. With these long odds on both fights, the move here is to parlay them. In my eyes, I see both of these fights as locks, so betting $100 on these seemingly sure things will get you sixty cents on every dollar. If you’re going to put down money, make it worthwhile and parlay the two.

Pick: Parlay Johnson (-800) and Souza (-225)

Image via Shutterstock

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Great American, mediocre student, terrible golfer. For lukewarm takes, you can find me at @mel_kiper_sr on twitter, or hit the inbox at

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