What seems unlikely now could become inevitable by 2028 if the Montreal Canadiens continue on this trajectory: Connor McDavid could sign with Montreal as a free agent when his current two-year deal with the Edmonton Oilers expires. This isn’t about market myth or sentiment. It will hinge on the world’s best player believing that it is the strongest path to winning.
Connor McDavid in the Canadiens’ Top Six Would Be Unstoppable
First line: Ivan Demidov alongside McDavid and either Alexander Zharovsky or Michael Hage. Juraj Slafkovsky with Nick Suzuki and Cole Caufield as their second line.
The Canadiens won six Stanley Cups between 1965 and 1979 with rosters so full of future Hall of Famers that some played only supporting roles. That era ended, and what followed was a franchise that relied more on goaltending and organizational pride than on offensive firepower. The 1986 and 1993 championships featured Patrick Roy standing on his head, not an embarrassment of skill up front.
Suzuki, Caufield, and Slafkovsky Lead Montreal’s Rising Core
The talent added over the last three seasons has built up a roster the franchise hasn’t seen in roughly 50 years, where skill isn’t just concentrated at the top; it is layered, with a defensive corps developing behind it that could make the team genuinely tough to beat in a way that pure offensive teams usually aren’t.
Suzuki has become one of the most complete centres in the NHL, posting 89 points in 2024-25 – the best individual season by a Montreal centre in nearly two decades. This season, he is on track to surpass that. Caufield, who scored 37 goals last season and has 35 with 22 games remaining this season, holds the franchise record for overtime winners and is aiming for 50, which no Canadien has done in over three decades.
Related: Suzuki and Caufield Are Canadiens’ Most Dynamic Duo in Decades
Slafkovsky, who many doubted for two years, is now among the most physically-dominant power forwards in the league, leading the team’s forwards in high-danger goals and top-speed bursts, turning wall battles into offence at a rate that even caught NHL legend Jaromir Jagr’s attention after the 2026 Winter Olympics.
Demidov has already proven that his offensive intelligence is legitimate, creating chances through anticipation and knowing where a play is heading two steps before most players. He is on track for 67 points, which would be the second-highest rookie total in the past eight years.
Second round 2025 pick Zharovsky broke the Kontinental Hockey League record for points by an 18-year-old this season, demonstrating how his creativity and instincts in tight spaces have already adapted to the professional game. The right winger’s skill set projects extremely well alongside elite linemates.
Hage is not just a backup plan; he is a fluid, powerful skater with a heavy shot and playmaking ability that make him a legitimate top-six option on his own, should Zharovsky’s timeline require patience.
Montreal already boasts one of the NHL’s deepest pools of young talent, and that’s before mentioning last season’s rookie of the year, defenseman Lane Hutson. This speaks volumes about the current state of the franchise. Oliver Kapanen also deserves a mention, sitting among the rookie leaders in goals this season with 19.
Why Canadiens’ Roster Could Tempt McDavid
Throughout his career, McDavid has been the league’s most dominant player, supported by a few elite teammates, while hoping the rest of the team can meet his standards. He understands the challenges of working with narrow margins, having played in two Stanley Cup Finals without winning a championship.
If projections hold, he would be joining a Montrean team that would not be asking him to carry it, but one that is already producing at an elite level. The roster is young enough that its best years are still ahead, and it retains cap flexibility to add rather than subtract as its window opens.
The salary cap is confirmed at $113.5 million by 2027-28. A $15 million commitment to McDavid is workable within a payroll that has deliberately avoided long-term deals that force yearly scrambles to stay afloat. The Oilers remain dangerous. Nobody serious is dismissing them. But they have only come close. They have not won a Stanley Cup. Thin margins can create doubt.
Related: Connor McDavid’s Legacy Being Tarnished After 2nd Straight Stanley Cup Final Loss
By 2028, the question will not be about market size or loyalty. It will be about conviction. If McDavid believes the Oilers give him the clearest path to a Cup, he will stay. If he looks at Montreal’s ascending core, its cap flexibility, its depth through the middle, and sees a team peaking at exactly the right moment, the calculation changes.
McDavid’s Legacy Could Be Defined in Montreal
A Cup in Montreal would be extraordinary. It would end three decades of suffering in one of the most hockey-obsessed markets on the planet. Still, McDavid has not given everything to the game to settle for a single championship and a parade. He has watched immortals like Wayne Gretzky, Mario Lemieux, and Sidney Crosby and understands what separates a legacy from mere excellence. The best don’t just win, they win again and again. That is what the Canadiens’ core could give him.
Demidov and his linemate, whoever they might be, won’t peak in 2028. They’ll still be peaking in 2031. Slafkovský will be entering the years when dominant power forwards become genuinely unmovable. Suzuki and Caufield will be in their prime. Stack McDavid on top of all that, and the Canadiens wouldn’t just be building a contender; they could be a dynasty.
If it’s not the Oilers, McDavid will be looking for a team built to win often, whether he says it publicly or not. He doesn’t want one brilliant run that’s followed by a rebuild, or a window that demands everything go right for one specific spring. He wants a team whose goal every October is clear.
Montreal’s Chance at Another Dynasty
Consider what building a dynasty would mean to the city. The Canadiens have 24 Stanley Cups, but haven’t won since 1993. Entire generations of Montrealers have grown up without a parade, hearing about the franchise’s legendary past daily. That gap is hard to reconcile because the drought isn’t just a statistic; it permeates every broadcast and every conversation about the Canadiens.
The day it ends, the city won’t just celebrate; it will erupt. If that breakthrough happens with McDavid at the centre and the wins begin to pile up, the conversation quickly shifts from ending the drought to asking whether this group can achieve something unprecedented in the salary-cap era. Winning multiple Cups in Montreal with McDavid leading the way would cement his legacy and mark it as a defining era in Canadiens history.
