Who will win the 2027 NHL Stanley Cup?
With the 2026 NHL Draft and the first day of “Free Agent Frenzy” in the books, it’s a good time to take a look at which teams improved themselves, which teams took a step back and the teams that remained status quo, allowing teams that were in their rear view mirror prior to July 1, 2026 to leapfrog past them.
Washington Capitals
I am going to start with the Washington Capitals. The Caps missed the playoffs by three points last season despite having 10 more regulation wins than the Philadelphia Flyers, who claimed the eighth spot. Today, the Caps announced that Alexander Ovechkin will return for a 22nd season and one more chance to win a Stanley Cup, with the off-season additions the team has made. Acquiring Alex Tuch in a sign-and-trade with Buffalo, Jordan Kyrou from St. Louis (for Connor McMichael), and free agents Boone Jenner and Vincent Desharnais provide the Capitals with significant upgrades. Twelve days ago, Washington was 50/1 to win the Stanley Cup and is now 22/1. Their odds for winning the Metropolitan Division have gone from 10/1 to 4/1, and they have gone from 25/1 to win the Eastern Conference down to 11/1.
NHL Futures Best Bets:
Capitals to win the Metro Division +400
Capitals to win the Eastern Conference +1100
Edmonton Oilers
The clock is ticking in Edmonton. Connor McDavid signed a two-year extension that starts this season. The Oilers made a controversial hire with Mike Babcock taking over from Kris Knoblauch as the new head coach. The spotlight is going to be on this team from day one of training camp, and the Oilers, who are notoriously slow starters, would do themselves a favor by coming out of the gate with a winning record in October. An “average team” is what McDavid called the Oilers last season, who were eliminated by the Anaheim Ducks in round one of the Stanley Cup Playoffs in six games.
I do have the Oilers as one of the “winners” of Free Agent Frenzy. Edmonton was able to move Darnell Nurse and his entire $9.25 million salary to the San Jose Sharks. In return, the Oilers received 24-year-old blueliner Shakir Mukhamadullin, who can slot in on the Oilers’ third pair. They signed former Pittsburgh Penguins defenseman Ryan Shea, resigned Connor Murphy, whom they acquired at this past year’s trade deadline, and already their blueline looks better than it did at the end of last season. Goaltending has been the biggest issue in Edmonton for the past five years. Edmonton had hoped that Tristan Jarry, who had won the Stanley Cup with Pittsburgh, would be an upgrade over Stuart Skinner when they made the goalie swap early last season. That ended up being a horrible trade for Edmonton. Late on Wednesday, the Oilers signed Stanley Cup-winning goalie Freddie Andersen to a one-year, $1 million deal (plus $1.8 million in incentives) as well as acquiring former Sabres goalie Devon Levi. While I have had my questions about Andersen over the years, he is an upgrade over Jarry. It will be interesting to see if the Oilers go with a tandem of Andersen and Levi and send Jarry to the minors.
NHL Futures Best Bets:
Edmonton Oilers to win the Western Conference +450
Edmonton Oilers to win the Stanley Cup +900
Over their October point total (TBA) – Best Bet
Florida Panthers
After winning the Stanley Cup in back-to-back years and three consecutive trips to the Final, the Florida Panthers missed the playoffs last season. Their three Stanley Cup runs add up to an additional 68 games (14 games shy of a full regular season), meaning that this group essentially played four regular seasons over the past three seasons. Injuries to their number one center, Sasha Barkov (missed the entire season), forwards Matthew Tkachuk (31 games) and Brad Marchand (52 games), along with defenseman Seth Jones (52 games), were just too much to overcome.
Not only will this team be better rested heading into the 2026-27 season, but the additions of Matthew Tkachuk’s brother Brady and the return of defenseman Radko Gudas make the Panthers deeper and nastier. Opponents better have their heads up when they play Florida this season. The biggest change in Florida is between the pipes, where Sergei Bobrovsky was not re-signed (signed with Toronto), and Jacob Markstrom (originally drafted by Florida) and Akira Schmid are the new goaltending tandem.
NHL Futures Best Bets:
Florida Panthers to win the Atlantic Division +220
Florida Panthers to win the Eastern Conference +425
Florida Panthers to win the Stanley Cup +700
Best Bets to Make the Playoffs
San Jose Sharks (-140)
The Sharks missed the playoffs by just four points last season. Their 27 regulation wins were more than two of their division rivals, LA Kings (22) and Anaheim Ducks (26), who made the postseason. San Jose bolstered their blueline with the additions of Jacob Trouba (free agent) and Darnell Nurse (trade with Edmonton). Ivar Stenberg, drafted second overall last week, has a legitimate shot of making the team out of training camp. If you are on board with the Sharks earning a spot in the playoffs, then I would also grab Macklin Celebrini (+650) to win the Hart Trophy (regular season MVP).
Best Bets to Miss the Playoffs
Ottawa Senators (+120)
The Senators traded their captain, Brady Tkachuk, and while they did acquire William Eklund from San Jose, I see the Sens as one of the teams who made the playoffs last season taking a step back. Both Florida and Toronto, who missed last season, are better than Ottawa in my opinion.
Philadelphia Flyers (-185) and Pittsburgh Penguins (-210)
If you have the bankroll that allows you to make this a two-unit play, I would highly recommend playing both these teams to miss the playoffs. The Penguins and Flyers were both pleasant surprises last season and exceeded expectations, but neither team has done anything to this point to make themselves better. I believe the Penguins and Flyers will be overtaken by Washington and New Jersey, knocking both out of the top three spots in the Metro Division. I see five teams from the Atlantic Division making the playoffs, leaving zero room for either Pennsylvania team.
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