Published on: June 21, 2026, 09:19h.
Updated on: June 21, 2026, 09:19h.
- The Toronto Maple Leafs are listed at +4000 to secure the Stanley Cup next season, with some sportsbooks offering +6000 odds.
- The Leafs have been active in the trade market, with several more moves anticipated in the coming days, establishing them as an appealing long-shot bet for the Stanley Cup before NHL free agency kicks off.
- The Boston Bruins are another intriguing long-shot option at +8000.
The most promising Stanley Cup futures bets often lie beyond the obvious favorites. These bets are on teams whose odds do not accurately reflect their potential. With the NHL Draft and free agency imminent, bettors have a fleeting opportunity to focus on long shots before offseason developments alter the betting landscape.
$4.4 Billion Valuation
The Toronto Maple Leafs hold the title of the wealthiest team in the NHL, boasting a valuation of approximately USD $4.4 billion, according to Forbes reports. The second-ranked New York Rangers stand at around $3.8 billion.
Last season was a major letdown for the Leafs, who opened October with +1600 odds to win the Stanley Cup, marking the ninth-shortest odds at that time.
As everyone knows, their season was fraught with struggles; they finished near the bottom of the NHL standings, fired General Manager Brad Treliving on March 30, well before the season’s conclusion—a clear indication of the season’s turmoil.
Bookmakers Hesitant
After the Carolina Hurricanes captured the Cup on June 19, sportsbooks quickly set their 2027 Stanley Cup futures.
Bookmakers are understandably cautious regarding the Leafs. The team’s odds see them placed as a middle-tier contender for the 2027 Cup, with +4000 at DraftKings, +3000 at FanDuel, and +6000 at Caesars Sportsbook. The Hurricanes continue to be favored at +700 on DraftKings.
The Leafs represent one of the most compelling long-shot futures bets in any major professional sport, especially with the NHL Draft (June 26-27) and NHL free agency (July 1) on the horizon. These critical events have the power to dramatically reshape team rosters, making this a unique betting opportunity that even die-hard Leafs detractors should consider.
New Management and Coaching Dynamics
On May 3, the organization appointed John Chayka as General Manager, followed by winning the NHL Draft Lottery on May 5, securing the coveted No. 1 overall pick in the upcoming Buffalo draft, likely to select Gavin McKenna, which could significantly revamp their first line alongside Auston Matthews and Matthew Knies.
Chayka dismissed head coach Craig Berube on May 13, and in the last week, he has taken significant action, recognizing that at least six roster moves are essential to contend for a playoff spot next season.
On June 17, he named Jim Hiller as the new head coach and initiated two substantial trades, recognizing the need to enhance the team’s defensive core. Goalie Joseph Woll and defenseman Simon Benoit were sent to the Philadelphia Flyers in exchange for promising defenseman Emil Andrae, goalie Samuel Ersson, and a third-round pick in this year’s draft.
Transformative Trade for Defense
Next, Chayka executed a major transaction by negotiating with the Tampa Bay Lightning to acquire the rights to what was projected to be the top free-agent defenseman available—Darren Raddysh. This strategic move attracted considerable interest from multiple teams.
In exchange for Raddysh’s rights, Chayka sent a fifth-round pick to the Lightning and signed him to an impressive eight-year, $68 million contract. Raddysh’s powerful point shot is a much-anticipated addition to the Leafs, having finished the previous season with 22 goals, 70 points, and a +21 rating, including 10 goals on the power play.
AHL Team Championship Win
Raddysh is also expected to revitalize the Leafs’ power play, which ranked 15th in the league last season at 21.3%.
Betting markets in Ontario are already featuring Raddysh with a proposition of +135 at FanDuel for scoring 65+ points next season.
Adding to the excitement, the Leafs’ AHL affiliate, the Toronto Marlies, clinched the Calder Cup, signaling potential reinforcements coming up from the minor leagues.
Available Salary Cap Space
This is quite a turnaround for an organization that has been mired in struggles for nearly a year.
With the salary cap slated to rise to USD $104 million for the upcoming season, the Leafs are positioned to make significant roster improvements.
As reported by PuckPedia, the Maple Leafs have approximately USD $18.8 million in cap room. With Max Domi potentially going on Long-Term Injured Reserve and trade talks surrounding defenseman Morgan Rielly (who earns $7.5 million annually), the team could have nearly $30 million in cap space as the offseason unfolds.
Noteworthy Mentions
The next ten days in Toronto could be pivotal, making those +4000 to +6000 futures more intriguing.
The market currently depicts them as a team that has failed rather than one undergoing a swift transformation.
For bettors looking beyond the Leafs, consider the San Jose Sharks who are also at +4000 on Caesars and +6500 on DraftKings. They boast an excellent prospect pool, emerging young talent, and $40 million in cap space, paired with the No. 2 overall pick in the forthcoming draft.
Bruins Present Significant Value
While not favored to win the Cup next season, holding a +6500 Sharks ticket could be preferable to many teams around +2500.
Additionally, bettors might want to consider the Winnipeg Jets, listed at +6000 on Caesars and +7000 on DraftKings, especially given their seasoned playoff experience and elite goaltending, as long as Connor Hellebuyck remains on the roster. If you’re betting with an eye towards next June instead of last April, the Jets are a contender to watch.
The Boston Bruins, sitting at +8000 on Caesars, boast elite talent in David Pastrnak and completed last season with 100 points, despite a first-round playoff exit against the Buffalo Sabres. This presents a significant value as they are not in rebuild mode, retaining $15 million in cap space while maintaining their core identity.