Posted on: June 21, 2026, 09:19h.
Last updated on: June 21, 2026, 09:19h.
- The Toronto Maple Leafs are at +4000 to win the Stanley Cup next season, with some books having them at +6000
- The Leafs have made a flurry of recent moves, with more likely on the way over the next few days, making them the top Stanley Cup long shot bet before NHL free agency starts
- The Boston Bruins, at +8000, present another good long shot betting opportunity
The best Stanley Cup futures bets aren’t always the favorites. They’re the teams whose odds fail to reflect their true upside. With the NHL Draft and free agency just days away, bettors have a narrow window to target long shots before offseason moves reshape the market.
$4.4 Billion Franchise Value
The Toronto Maple Leafs are the richest team in the NHL, with an estimated valuation of USD $4.4 billion, if you believe those Forbes stats. The New York Rangers are second, at around $3.8 billion.
The Leafs were one of the NHL’s biggest disappointments last season, opening last October at +1600 to win the Stanley Cup, the ninth-shortest odds on the board.
Everyone knows how that turned out. The Leafs were awful for a slew of reasons, finished fifth last in the NHL, and fired their General Manager, Brad Treliving, March 30, before the regular season even ended. That’s how badly their regular season went.
Bookmakers Skittish
Sportsbooks, just days after the Carolina Hurricanes hoisted the Cup (June 19), posted their 2027 Stanley Cup futures.
Bookies are skittish when it comes to the Leafs, which is completely understandable. The Leafs are middle tier on the futures board for Cup winner in 2027, +4000 at DraftKings, +3000 at FanDuel, +6000 at Caesars Sportsbook. The Hurricanes are betting favorites to defend their title, at +700 at DraftKings.
The Leafs are also one of the best long-shot futures bets on the board in any major professional sport, with the NHL Draft (June 26-27) and NHL free agency (July 1) just around the corner. Both the draft and free agency can dramatically reshape a roster, making this a betting opportunity that even the most ardent Leafs haters shouldn’t turn their backs on.
New General Manager, New Coach
The organization hired John Chayka as GM May 3, followed by winning the NHL Draft Lottery May 5, securing the No. 1 overall pick for the draft in Buffalo (likely to be Gavin McKenna, which could potentially remake their No. 1 line, along with Auston Matthews and Matthew Knies).
Chayka fired head coach Craig Berube May 13. Then this past week he really went to work, knowing the Leafs have at least six roster moves to make if they plan on getting back into the playoff conversation for next season.
He hired a new coach (Jim Hiller) on Wednesday (June 17) and followed that by swinging two substantive trades. Knowing he needed to start re-working the team’s back end, goalie Joseph Woll and defenseman Simon Benoit were traded to the Philadelphia Flyers for young defenseman Emil Andrae, goalie Samuel Ersson and a third-round pick for this year’s draft.
Raddysh Trade Remakes Defense
Then Friday, Chayka swung huge – a sign and trade with the Tampa Bay Lightning to secure the negotiating rights to what would have been the top free agent defenseman available once the market opens, no doubt attracting a lot of interest and bids involving multiple teams – Darren Raddysh.
Chayka only sent a fifth-round pick to the Lightning for Raddysh’s rights, then signed him to an eight-year, $68 million contract, a major cog in remaking the team’s back end. Raddysh has a cannon for a point shot, which the Leafs haven’t had on their roster for decades, finishing last season with 22 goals and 70 points, a +21, including 10 power play goals.
AHL Team Wins Championship
He’ll help turn around a Leafs’ power play that dipped to 15th in the NHL last season, at 21.3%.
The hockey-mad Ontario market is already being offered Raddysh betting markets – Raddysh to scored 65+ points is +135 at FanDuel.
Then Friday night, the Leafs’ American Hockey League (AHL) team, the Toronto Marlies, won the Calder Cup, the AHL championship, suggesting help is on the way from the minor league affiliate as well.
Salary Cap Space
Not a bad week for an organization that had been in a depression for nine months.
The Leafs, with the salary cap going up to USD $104 million for next season, can spend their way out of the doldrums.
According to PuckPedia, the Maple Leafs have just under USD $18.8 million in cap space. With Max Domi, making $3.75 million this upcoming season, possibly going to Long-Term Injured Reserve, plus trade rumours building around defensemen Morgan Rielly, making $7.5 million per year, the team could potentially be looking at closer to $30 million in cap space to spend as the off-season evolves.
Honorable Mentions
The next ten days could be a game changer in Toronto, putting those +4000 to +6000 futures into focus.
The market is pricing them as a failed team rather than a team undergoing a rapid rebuild.
Honorable mentions, alongside the Leafs, for bettors?
The San Jose Sharks, +4000 at Caesars, and +6500 at DraftKings, for one. Talk about a lottery ticket – one of the best prospect pools in hockey, elite young talent already arriving, assets to make major trades, and $40 million in cap space according to PuckPedia. The Sharks already own the No. 2 overall pick in the upcoming draft.
Bruins Offer Big Value
Are they expected to win the Cup next season? No. But would bettors rather hold a +6500 Sharks ticket than many +2500 teams? Absolutely.
Bettors could also look at the Winnipeg Jets (+6000 at Caesars, +7000 at DraftKings, $21 million in cap space), a proven playoff team, with elite goaltending (as long as Connor Hellebuyck doesn’t get traded), a huge equalizer in the post season. If you’re betting for next June rather than last April, Winnipeg is worth the consideration.
The Boston Bruins are +8000 at Caesars, with David Pastrnak still an elite star, and the fact they finished the season with 100 points, losing out to the Buffalo Sabres in the first round of the playoffs, that’s big value. Unlike San Jose, the Bruins aren’t rebuilding, and hold $15 million in cap space. They know their identity.
Recent Comments