Connor McDavid’s chances of winning a Stanley Cup with the Edmonton Oilers remain alive — but the road is treacherous
While his individual brilliance puts the team within striking distance, hockey is the ultimate team sport. Success demands more than just one superstar.
If the Oilers can shore up their weaknesses and find consistency, they absolutely have the talent to win it all.
But if history repeats itself — defensive breakdowns, goaltending errors, missed opportunities — McDavid may one day have to chase that ring elsewhere.
If the Oilers turn it around and finally win that elusive Cup in the next season or two, all of this becomes moot.
McDavid stays. Statues are built. Legends are written.
But if Edmonton keeps falling short, and if the cracks in the foundation grow wider, then we may see the end of an era.
Stan Fischler’s suggestion might seem far-fetched now, but sports are full of shocking moves that once seemed impossible. LeBron James left Cleveland. Tom Brady left New England. Wayne Gretzky left Edmonton. Connor McDavid?
Also Read: Leon Draisaitl’s Custom Connor McDavid T-Shirts Marking 1,000 Points Go Viral
Table of Contents
Connor McDavid: Hockey’s Uncrowned King
Connor McDavid’s career has been a display of brilliance, consistency, and generational talent.1
Since being drafted first overall in 2015 by the Edmonton Oilers, McDavid has become the face of the NHL, the gold standard for offensive production, and a perennial Hart Trophy candidate.
Yet, for all his personal accolades and statistical dominance, the one thing that continues to elude him is hockey’s ultimate prize—the Stanley Cup.
Despite leading the league in points multiple times and delivering jaw-dropping highlight reels nightly, McDavid’s name is still missing from the list of Stanley Cup champions. And in hockey, that matters. A lot.
Looking forward to lacing them up for Canada at #4Nations Face-Off! @Rogers customers be sure to enter for your chance to win a VIP trip to watch us play live at https://t.co/JOA0LNYe1t #BeyondTheSeat @NHL @NHLPA https://t.co/8WrJZYjdth
— Connor McDavid (@cmcdavid97) January 26, 2025
The 2024 Heartbreak: Inches From Glory
The Edmonton Oilers’ most recent playoff run felt like a script written for redemption. Down 3-0 in the Stanley Cup Final, McDavid and the Oilers clawed back with gutsy wins, tying the series and forcing a decisive Game 7.
Hopes soared. Yet in the biggest game of his career, the Oilers fell just short—again.
It was a crushing blow for a team that had seemingly turned the corner and, more poignantly, for a player whose legacy now balances on a knife’s edge.
If McDavid were a quarterback or NBA superstar, this would be the equivalent of reaching a Super Bowl or NBA Finals only to walk away without the trophy—agonizingly close, but not quite enough.
Connor McDavid: Stanley Cup or Bust
The Weight of Greatness
No player in the NHL faces more pressure than Connor McDavid. Wayne Gretzky had his Cups.2
So did Mario Lemieux, Sidney Crosby, and Alex Ovechkin. Each had to climb the mountain, often facing years of frustration before breaking through. But time, even for the greats, runs out.
McDavid is still in his prime, but he’s also not the 19-year-old phenom anymore. The Oilers have built around him—Leon Draisaitl, Ryan Nugent-Hopkins, and a rotating cast of role players—but something always seems to go wrong.
Whether it’s goaltending inconsistencies, defensive lapses, or bad injury timing, Edmonton has never quite sealed the deal.
And that persistent failure raises the inevitable question: How long is McDavid willing to wait?
The Gretzky Parallel: History Repeating Itself?
In 1988, the hockey world was stunned when Wayne Gretzky was traded from Edmonton to the Los Angeles Kings.
The trade shook the sport and marked a pivotal moment in NHL history. Though the circumstances were different—Gretzky was traded, not a free agent—the echoes of that move still resonate.
McDavid isn’t Gretzky, but the parallels are impossible to ignore. A generational talent in Edmonton, held back not by individual failure, but by a team that couldn’t quite get over the hump.
Hockey insider Stan Fischler recently floated the possibility of McDavid pulling a “Gretzky”—leaving Edmonton in pursuit of a Cup, potentially with a franchise like the New York Rangers.
It’s speculative, of course. But it’s not unreasonable.
Connor McDavid: New York Rangers
A Tempting Destination
The Rangers are among the NHL’s most prestigious franchises, both historically and financially.3
With a current valuation of $3.5 billion (per Forbes), they have the resources, the market, and the mystique to lure any player. Add to that a passionate fan base and a roster already brimming with talent, and the picture becomes even clearer.
A move to Madison Square Garden wouldn’t just give McDavid a new hockey home—it would turn him into a global superstar.
It’s the biggest stage in the world, and McDavid could elevate his brand beyond anything possible in Edmonton.
He’s already the best player in hockey. New York would make him the most famous.
Contract Realities: Free Agency Looms
As of now, McDavid is under contract with the Oilers through the 2025-26 season. But NHL timelines move quickly, and decisions about a player’s future are made well before the final year of a deal.
If McDavid signals any uncertainty about re-signing, Edmonton would be forced to make an impossible choice: risk losing him for nothing, or trade the most talented player of his generation.
The power is increasingly shifting toward star players in the NHL. Like in the NBA or NFL, players have learned how to leverage their status to control their futures.
If McDavid wants out, even without demanding it, he could subtly steer the Oilers toward a trade—or simply wait for free agency.
Legacy on the Line: Rings Define Greatness
Fair or not, greatness in sports is often defined by championships. Dan Marino was an all-time quarterback, but he’s remembered just as much for not winning a Super Bowl.
Charles Barkley, Patrick Ewing, and Steve Nash were legends of the hardwood—yet a missing ring haunts their legacies.
McDavid is rapidly approaching that conversation in hockey. Everyone knows he’s elite. Everyone knows he’s generational. But in a sport where names like Crosby, Gretzky, and Yzerman are enshrined in Cup lore, McDavid’s lack of a title looms large.
If he wants to be remembered as not just the best player of his era, but an all-time winner, something may have to change.
Edmonton’s Window: Is It Closing?
- The Oilers’ recent runs show they are close—but being “close” year after year can become a trap.
- Window-chasing teams sometimes mortgage the future to win now, only to fall short and then collapse. Edmonton still has talent, but the Western Conference is brutal, and nothing is guaranteed.
- Goaltending remains a question mark, and defensive depth is always a concern. Draisaitl is incredible, but he’s also set to become a free agent in 2025. If he leaves, that could signal a domino effect. McDavid might not want to be the last one holding the puck in Edmonton.
- From a loyalty standpoint, McDavid owes Edmonton nothing more than what he’s already given: generational greatness and unrelenting effort.
- But emotionally, fans will always hope he stays. The idea of him hoisting a Cup in orange and blue is deeply romantic—a storybook ending.
- Yet pragmatism has a way of trumping sentiment. If McDavid believes he can’t win in Edmonton, then moving on isn’t betrayal—it’s ambition.
Also Read: Connor McDavid’s Response to Matthew Tkachuk’s Punches During the Stanley Cup Final
Can Connor McDavid Get a Ring with the Oilers?
Breaking Down the Chances
Connor McDavid is widely regarded as the most electrifying player in the NHL today.
His speed, vision, and playmaking ability have made him the face of the league, but there’s still one accolade missing from his resume — a Stanley Cup.
As the Edmonton Oilers grapple with the pressure of postseason play, fans and analysts alike are left wondering: What are the chances McDavid finally gets a ring with the Oilers?
Let’s examine the current playoff scenario, McDavid’s role, team dynamics, and what the future holds.
A Rough Start in the Conference Finals
The Oilers seemed poised to steal Game 1 against the Dallas Stars in their Western Conference Final matchup.
They had momentum, defensive discipline, and offensive creativity working in tandem — until it all fell apart in the third period. Dallas stunned Edmonton with a five-goal onslaught, flipping what looked like an Oilers win into a painful loss.
Losing the opening game in such dramatic fashion has had ripple effects. According to FanDuel, Edmonton’s title odds dropped to +380, making them the second-least favored team among the final four.
Although a Game 1 loss doesn’t seal a team’s fate, the psychological blow was real.
Connor McDavid: Brilliance Under Pressure
McDavid’s brilliance is unquestioned. A multiple-time Hart Trophy winner and Art Ross recipient, he consistently ranks among the league leaders in points.
But his performances in the playoffs have sometimes been overshadowed by defensive lapses or lackluster goaltending around him.
Still, McDavid has carried the Oilers deep into the playoffs before — reaching the Western Conference Final in 2022 and now again in 2024. His commitment is clear. The real question is whether the rest of the team can rise to his level.
The Supporting Cast: Strong But Inconsistent
Leon Draisaitl is the perfect co-star for McDavid, providing scoring and a physical presence. Zach Hyman has been a goal-scoring machine in the postseason. Evan Bouchard, an emerging two-way defenseman, has impressed with his offensive flair.
However, inconsistency haunts the Oilers. Players like Ryan Nugent-Hopkins, Evander Kane, and Darnell Nurse have had their moments but haven’t always shown up in crunch time.
Edmonton’s defensive breakdowns — like the one seen in Game 1 — are a recurring concern.
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Goaltending Woes Continue
Goaltending remains Edmonton’s Achilles’ heel. Stuart Skinner has shown flashes of brilliance but also periods of extreme vulnerability.
The team’s inability to find a consistent, elite-level goalie could ultimately be what derails their Cup ambitions.
Past teams with legendary forwards — think of Alex Ovechkin’s Capitals pre-2018 — were often undone by inconsistent netminding. McDavid and the Oilers are in a similar boat unless this critical piece is resolved.
Coaching and Tactics: A Mixed Bag
Head coach Kris Knoblauch has made notable adjustments since taking over midseason.
His approach favors speed and high-tempo offense, perfectly suited to McDavid’s game. But the lack of defensive structure at key moments continues to be an issue.
Game 1’s collapse was partly due to poor in-game management. Defensive coverage fell apart, and there were no timely timeouts or tactical changes to stem the bleeding.
To win a Stanley Cup, coaching needs to be as elite as the players.
Also Read: Connor McDavid’s Playoff Controversy: Fans Demand Suspension for High Stick on Carson Soucy
